Trying Too Hard

trying too hard style fashion

The concept of “trying too hard” irks me. People are constantly being criticized for putting forth minimal effort, and yet we censure them for being overly enthusiastic, too. Talk about a lose-lose proposition.

And yet, I’ve gotten several reader questions about “trying too hard” stylistically, and I understand why. When I was 13, I felt certain that simply OWNING and WEARING cool clothes would make me cool … but when I got my hands on an entire Esprit ensemble and wore it to school, I was still shunned. And the feeling I had? Trying too hard. Specifically trying too hard to fit into a group that didn’t want me, trying too hard to adopt a style that had nothing to do with my own tastes, trying too hard to be someone I’d never be.

As an adult, I’m still susceptible to the delusion that buying and wearing cool stuff will make me cool. But I’ve learned that even cool items can become uncool if they clash with the wearer on a personal level. In my opinion, there are three main actions that will trigger that “trying too hard” feeling:

  • Wearing something that doesn’t feel like it aligns with your personal style
  • Dressing specifically to attract attention or garner compliments
  • Crafting looks that feel over-the-top or excessively showy to you

We all do these things on occasion, and they are healthy and normal. How else are we supposed to expand our wardrobes and allow our styles to evolve if we don’t wear items that fall outside our comfort zones? What’s wrong with wearing something we know looks amazing and hoping that friends will dish out a few much-needed compliments? What fun is life if we don’t get glam and dramatic sometimes? Making a habit of any of these three, though, may cause you to feel off-kilter, lost, and potentially like you’re … well, trying too hard.

That said, my guess is that folks who are frequently plagued with worry about their levels-of-stylistic-trying may have to deal with peer scrutiny, a vocal and judgmental friend group, or some form of outside input that creates fears of dressing “the wrong way.” Dealing with someone who verbalizes negative opinions about the dressing choices of others – not necessarily yours, but even celebs or strangers – can give a gal a complex. Because in a neutral or supportive environment, showy outfits generally generate discussion and neither the wearer nor the observers feel compelled to deem them “good” or “bad.” A neutral or supportive environment will often encourage self-expression and see behavioral changes as points of interest instead of potential threats. But a judgmental environment will cause self-consciousness, doubt, and fear of retribution for branching out or rocking the boat.

I believe that confidence is the key to overcoming concerns of trying too hard. If you have a highly vocal peer group to contend with, push yourself – and them – a little at a time. If an entire outfit is too scary, wear one or two pieces that you feel might verge on “trying too hard.” If they draw comments, deflect them with humor. One of my favorite ways to defuse situations is to laugh along with the commenter. β€œHahaha, I know! Isn’t this WILD?” tends to work wonders. You’re acknowledging that you’re doing something different, reinforcing that you’re enjoying the exploration, and showing that you have no intention of being cowed into some sort of apology for your tastes and stylistic choices.

Now, if your internal voice is putting a damper on your efforts to explore new avenues of style – if it’s just you who is cooking up fears of trying too hard – here’s my advice: Fake it. Wear items or outfits that feel uncomfortably bold, and pretend like you totally own the looks. Whenever you pass a mirror, look at yourself and say, “I look AMAZING in this!” Walk tall, mind your posture, and smile. Keep it up, on a schedule if necessary: Twice a week, then three times, then four … Eventually, you’ll feel as confident as you look and those worries about trying too hard will begin to dissipate.

Image courtesy Dave77459.

Originally posted 2011-04-27 06:19:27.

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68 Responses to “Trying Too Hard”

  1. Autie

    What a great post. I remember a girl was moving in on “my” guy (somehow that’s always how it goes) and she dressed like a punk rocker – in fact, she WAS a punk rocker. So I thought I’d have the upper hand if I went from my breezy, chambray shirt style to her dark, skinny jeans + band shirts look. It’s embarrassing to look at pictures from that phase, especially because the guy liked how I dressed BEFORE I changed my look. Good thing the girl moved away, haha! Thanks for the reminder to just be me.

  2. Laura

    Even at 28, sometimes feel like I’m “trying too hard” when I wear an outfit that’s just not ME. It’s taken me awhile to figure out what I like and define my own personal style, and when I don’t get it right or step out of my comfort zone to an extreme degree, I just feel like I’m in a costume. Like, I’m Laura Dress Up As Something rather than just Laura.

    But honestly, I admire those who are willing and comfortable trying something new and shaking up their own style. I think the whole “trying to hard thing” only applies when someone isn’t themselves in their outfit. I think dressing flashy or for attention actually suits some people (a la Dolly Parton or Lady Gaga.)

  3. Relatable Style

    I have no answer to most of your questions, as I don’t really remember ever feeling like I’m “trying too hard”. I do remember being perceived as such, though, when I got contacts over the summer when I was 14 and then got back to school. And a guy from my class, who I never had any kind of beef with and was also wearing glasses, immediately said to me in a hateful tone “Just go back to your glasses, you stupid cow”. Well, I did make an impression on me, but I shrugged it off and of course I kept on wearing my contacts. Who’s he to say what I’m going to do? Sheesh.
    Today, I do what you suggest in your post… If someone points out I’m wearing something out of the ordinary, I just say “Cool, right?” or something of the like. And that’s it. But I secretly hate that they even feel the need to point it out. Some women do it for amusement and to single you out, and while I don’t perceive it as particularly mean, I think it is petty. And petty is one thing I definitely don’t like!

  4. Cynthia

    Before I started style blogging, I had a habit of buying fabulous items that I loved and then not wearing them because they were “too much” for my super casual work environments where some of my colleagues look positively scruffy. I’ve been dealing with it by wearing some of my fabulous items, and buying even more fabulous items, and no one seems to notice (at least in a negative way). Sort of what you said — get accustomed to making an effort by slowly ramping up.

  5. Lisa

    I am so uncomfortable in “MY STYLE” that until I found your blog I was lost and would stay within my comfort zone. After losing weight, I wanted to shop shop shop…. but as I did… I noticed that I left the clothes hanging in my closet and always went back to MY SAFETY NET…. Thanks as always for this wonderful article…. I am making progress…. a little at a time… OH and the comments…from family and friends… I usually just smile and try hard not to show…how afraid I am to walk out of my comfort zone!.

    • christine

      I can relate to this. You’ll get there, just be patient with yourself. Congrats on the weight loss.

      One suggestion that helped me was to always say thank you whenever I received a compliment. The simple thank you shows I acknowledge the compliment and it helps me accept it as well.

  6. Alex

    Depending on how confident I’m feeling, I definitely have trying-too-hard days. I don’t think of them as a bad thing, necessarily. Pushing my style boundaries and learning how to put my own spin on trends I enjoy means I sometimes spend a lot of time putting together a pretty basic outfit. I’m okay with it. (I just keep telling myself that it will get easier and increasingly effortless with time!)

    Yesterday was one such day. I bought royal blue tights the day before on a whim and was eager to try them. My skirt ended up being a little shorter than I anticipated and, well, there was a LOT of blue (my legs are neither long nor thin/in particularly good shape). I looked in the mirror and thought, “Okay, I’m either going to look awesome or ridiculous today. Either way, going to act like it’s awesome no matter what.” I’m sure people saw me and thought, “Oh dear, trying too hard,” but I had a lot of fun and even got a few compliments–exactly how I like to deal with feeling like I’m trying too hard.

  7. Kristen

    Yes, I have felt that way. I think it happened to me when I entered the super professional office environment straight out of college and thought I needed to fit in by wearing button-downs and other really conservative pieces. And black pants. I actually HATE black pants, button-downs and really conservative pieces and when I re-built my wardrobe post-baby, I ignored buying things that fell into those categories and only bought things that felt like me, which is more brown-safari-style-based. I look professional, but feel like myself. Win win.

  8. Elissa

    Sal, this post is genius. Thank you for putting a voice to an issue I’ve had since I was an adolescent. I can absolutely relate to buying clothes simply to feel “cooler” only to find I was the same old weird me underneath. I believe that this is an issue of self-confidence – if I felt stronger, and better about my body, I would not feel the need to use my clothes as a tool for self-acceptance. Now that I’m blogging I definitely feel more pressure to ramp up my personal style, and I struggle with seeing my clothing choices as a tool for self-expression rather than for social acceptance. When I dress as I think I “should”, and try to fit myself into a mold that isn’t cut for me, I feel uncomfortable and out of balance. So I’m working on challenging that.

  9. Elizabeth

    Oh man, Esprit! I was certain they’d like me if I got Esprit too! My parents, who were not well off, arranged to give me an Esprit Christmas one year. My mother supplemented the trademark Esprit pieces with other stirrup pants in basic colors. In January when I returned to school they girls immediately ridiculed my non-Esprit pants and mocked me for wearing the same Esprit sweatshirts to school each week. Man, they were mean.

  10. Ashley

    I actually wrote a post last week on my blog where I expressed my frustration with feelings of not dressing like “me”. I was definitely trying too hard and wearing clothes that made feel uncomfortable. I was dressing for my blog and not for myself. So last week I decided that from now on I would dress for myself (not that I can’t still be inspired by others) and so far getting dressed in the morning has been a lot less stressful.

    Great post on a great topic!

  11. Bubu

    Wow, what a great post. Have definitely had that icky feeling and sometimes I can move past and sometimes I can’t. But almost always when I push outside my boundaries I really enjoy what I’m wearing, and don’t care what others think. But that voice inside, that caring and trying with your clothes and style, is somehow a sign of vanity or shallowness, can crop up and I have to take all i’ve learned about myself and my values and beliefs to not fall prey to it.

  12. Andi

    I don’t usually have problems with trying too hard, what I have problems with is that nobody in my immediate circle acknowledges effort to your face! For example, I can wear a great outfit or a new pair of shoes or a statement necklace and very few people say anything directly to me — but I hear later that they said something positive to my BFF or the hubs or….

    For those people who feel they get ignored or dissed when they dress up, it really is your social circle at fault and they may simply be stunned into silence by your awesomeness.

  13. style odyssey

    wow, great post. i think your observations are spot on.

    i never felt in high school that i was trying too hard. of course, that was the early 80s, and there was no such thing as making too much effort in those days, lol!

    fast forward to present day: one of the reasons i started a style blog was so i’d have a personal journal i could refer to through time, to note how my style evolves (or doesn’t), and to discover missteps as well as successes. i can look through and notice where i was trying too hard, which came from buying and wearing things that didn’t feel very “me”, all because i shopped emotionally (“hey, that’s cool, i’m buying it!”) editing one’s wardrobe is key to avoiding that trying-too-hard look.

    why have i tried too hard in the past? because i’m a creatively- experimental person by nature. i simply like to try out new things but i’ve learned to edit…it’s not easy sometimes, and i often wonder if there’s such a thing style-schizophrenia! πŸ˜‰ *lol*

  14. style odyssey

    i meant to add: esprit was the bee’s knees when i was in my late teens/early 20s!! well-made clothing that was uber cool. i’ll never forget when i could finally afford a few esprit pieces- they became my trendy wardrobe staples for several years. i wonder what happened to the brand…

    • M.

      It still exists, it is pretty popular in Europe, something along the lines of Gap or Banana Republic in terms of classic pieces. It is still too pricey for me, but sales can be good.

      • Pauline

        Is popular in Australia too. Now I am in the US I buy online and the sales are usually really good and the outlet store always seems to have a good array. Good for quality basics. I just had a little splurge there – as they’ve got a 40% off sale on.

  15. Rad

    I only would use “trying to hard” in a few contexts, but mostly I felt that way about a couple of my male friends, who were trying too hard to be accepted by a certain group of people. One boyfriend was a dedicated hipster who spent hours at consignment and vintage shops, trying to find the perfect everything. It wasn’t dedication to style that bothered me, it was the dedication to style with the hopes that the certain artistic community in Brooklyn (Manhattan born/bred Dalton school education artists, film makers, and publishing types) would suddenly accept him and take him into his fold. I guess it bothered me because I saw it as part of a larger attempt on his part to reject who he was, which was a public university professor from a somewhat humble immigrant background, who was also a lovable dork. It sort of made me sad. While I don’ disparage his choices, after a while his envy and dissatisfaction kind of stressed me out, so we stopped seeing each other.

  16. Casey

    Occasionally, like most women, I have felt like I was trying too hard. Usually it involved wearing a more extreme look or a style that I wasn’t quite sure was “me”. An example would be how for a period I wore a lot of very “costumy” vintage pinup looks from head to toe. I adore gals who pull this look off everyday with panache, but I found that for me I was trying too hard and never completely comfortable with how I looked (plus I was spending more time in front of the mirror each day that I really have time for!). So I took bits and pieces of what I did like and molded them into my own aesthetic sense. But I never would have discovered some things without going out on a limb, and yes, looking like I was trying too hard for a bit! πŸ˜‰

    That being said, a lot (and I’m not joking here) people still take the effort to point out how I’m dressed on a daily basis. Which I sometimes perceive is their way of trying to tell me I look (to them) like I’m trying too hard. What I think other people sometimes fail to realize is that some women (and men!) aren’t trying to be showoffs, but are just extremely comfortable with standing out from the crowd. I still like very theatrical, dramatic pieces and looks, even though people have and will perceive them as “trying too hard”. It’s just how I am! πŸ˜‰

    β™₯ Casey

  17. Jessica

    This has definitely happened to me. Part of the reason I started blogging was to motivate myself to put forth more effort in my work wardrobe. But, as soon as a I started “dressing up” my co-workers were very vocal and it began to make me really uncomfortable. There’s only so many times you want someone to ask you why you’re so “gussied up.” When I mentioned it to my mom, she told me not to pay attention, to keep dressing how I wanted and eventually they would get used to it. That’s a work in progress, but it is getting better and I love having more fun with my work clothes. Even if I have to deal with a few people bothering me over it.

  18. Sara

    I was just thinking of the phrase “trying too hard” this morning and here you’ve written so wonderfully about it! I agree with you that, with confidence, one can pull off pretty much anything. Posture is so hugely connected to confidence, something I didn’t realize until I started style blogging.

    For me, when I feel like I’m trying too hard, it usually means I’ve loaded up on accessories, or put some things together that feel different for me. I think there are wonderful lessons to be learned with wearing those things that are a bit beyond the comfort zone, that might feel “too hard.” When I wear those things, at the end of the day I usually feel pretty proud of myself for doing something that felt a bit out of the ordinary.

    Great post (as always, Sal).

  19. Mel

    I’ve never felt that I had a nice wardrobe, ever. It’s never been a case of trying too hard. I just recently (at the age of 59!) have become more attuned to style…having viewed it as a shallow indulgence all this time….not realizing that it’s really all about making the body I have look good, not so much about spending money frivolously.

    A blog recently had a posting about “What does your outfit say about you today”. The posting and comments really got me to thinking….my outfits say nothing. They’re just there. They don’t SAY anything.

    Aha! Light bulb goes on! I’m a really fun, lively person….what am I doing???? Why do I dress so boringly???? Stop that!!!! So I’ve been looking with a more critical eye as I put outfits together, dug out Mom’s cool scarves to try, starting using my jewelry more.

    Realized that I don’t accessorize enough. You know how you hear, get dressed, look in the mirror, take one thing off? Well, I need to look in the mirror and ADD two or three things. I can’t get over what a difference a scarf makes!

  20. Erin

    Wow. This article TOTALLY spoke to me. I mean, you really hit the nail on the head here! Who among us HASN’T felt this way at some point? But you put feelings into words in a very clear, well thought out way. I am highly impressed and will probably reference this article again in the future. Well done, you!

  21. rb

    I had forgotten about the “trying too hard” feeling until you posted this. Yes, I felt that with my first corporate job, wearing a suit and carrying a briefcase. I was 22. I felt like I was pretending to be a grownup.

    Now I’m 46 and don’t really worry about that sentiment. I might if I were wearing clothing too tight or revealing for me (the phrase “mutton dressed as lamb” springs to mind) but of course I don’t dress that way.

    OTHERS might see me as “trying too hard” on occasion because I am usually a fairly dressy dresser, but from my point of view, that’s their problem, not mine. πŸ™‚

  22. Tiffany

    your second action, the “dressing to garner compliments or attract attention” seems to be one of the more common mistakes I see in the world of style blogging, and I’ve fallen victim to it myself in the past. It’s easy to get caught up in trying to wear only the most comment-worthy outfits but if what you’re wearing doesn’t jive with who you are then it will show. It all boils down to motivation- intrinsic motivation to try new styles and push your own limits for self-growth is perfectly fine but buying those brand new Litas because every popular blogger you follow has a pair is ridiculous and it’s a surefire way of wasting money on things that won’t serve you well in the long run. As you said, it’s one thing to challenge yourself but it’s another to compromise yourself. People can see and sense the difference, and by trying too hard you’re only hurting yourself.

    (obviously all the “you”s are abstract and not directed at you specifically, Sally.) Great post, it’s good to have this reminder to BE OURSELVES.

  23. Maythe

    I’m so lucky in my friends. I can turn up to a party in jeans and a manky t-shirt and they love me, I can turn up in a corset and heels and they love me (with a side of extra drooling, which is nice). I’d question whether a friend group which is critical really consists of friends? Obviously ‘peer group’ includes family and co-workers you have no choice about interacting with but if ‘friends’ regularly diss you on the basis of your clothing choice they need a good friend-dumping in my view.

  24. Mouse

    I feel like I’m “trying to hard” if I try to wear anything fancier than jeans + t-shirt + zipper hoodie + sneakers or rain boots. When I do try, I feel like the ugly duckling who isn’t fooling anyone with my swan costume: a pitiable creature trying to step out of her place.

    • M.

      I used to feel like that and missed out on a lot of clothing items I did not dare to wear. How about trying Sal’s advice and switching one item at a time, maybe not wear sneakers one day, or some casual skirt instead of jeans? It helped me to gain more confidence, and even if you are not a swan – few people are – you can be a confident duckling, or an entirely water fowl altogether, if you don’t mind me carrying the analogy too far. Nothing wrong with jeans/sneakers/sweaters if it makes you comfortable, but I wish you luck in expanding your wardrobe if you yearn to wear different things.

      • Mouse

        Thank you for the comment. πŸ™‚ I was feeling a little bitter when I posted mine, as I’m sure you could tell, haha. Most of the time I’m pretty comfy in my jeans and hoodies, but when I went on a trip to another (much warmer) city last summer, it was far too hot for such clothes and I was forced to turn to skirts and summery shirts. When I was wearing those clothes, I felt like I actually wanted to be out in public and be seen, because I felt like I looked good.

        Then I came home and put all of my cool weather clothes back on. It’s just starting to get warmer this year, so now would be the time to start wearing skirts again, but it feels weird to get dressed up just to go to work. I don’t really know why, it just does. Which is kind of funny, because work is the ideal place to wear skirts! If I tried to wear them hiking or wherever, my legs would get all scratched up. I think a big part of it is just that I live in a small town, so (as the old saying goes) I’d be all dressed up with no place to go.

  25. M.

    Very interesting topic, would you be willing to extend on the theme a bit? I’d love to hear your and your readers comments. Several people here seemed to have to deal with some form of bullying based on “trying too hard” to fit in. Personally, it took me a decade after being bullied in middle school to actually wear what I would like, instead of being in constant fear of being ridiculed or accused of “copying”. I did not dare asking for popular items, since I felt that I was not allowed to wear them on account of being uncool. I got over it, but how much do you think does that affect peoples wardrobe choices way past school?

  26. Michelle

    I like a mix of casual dressing with dressy dressing. When I’m feeling down, I love to put on an outfit that makes me feel like an old movie star or otherwise glamorous lady.

    This went by without comment when I lived near Philadelphia. But when I moved to Florida – you very rarely see anyone in dresses, it is sandals and capris all the time. I have gotten funny looks for wearing dresses (and I’m not talking ball gowns, stuff I would have worn to work) to Mom’s Nights Out. If I put on a nice hat, it’s all over.

    If asked, I’d gladly explain that I’m not trying to hard to impress them, I’m trying to feel good about me! I stay at home mom, my daily uniform is extreme casual by necessity! Please allow me nights out to explore the rest of my wardrobe!

  27. Jenna S.

    I think it has a lot to do with the environment I’m in. I go to a fairly laid-back liberal arts college where it’s not normal for people to wear uniforms of t-shirts, hoodies, sweats, leggings, Uggs, flip-flops, elastic headbands, and bookbags. This irks me, because I normally pride myself on putting thought into my appearance and looking polished and put-together. For the first couple of years, any fashion risks outside of jeans and a casual shirt felt like I was trying too hard.

    I gradually pushed the boundaries, though, little by little, and now I’m comfortable wearing colorful flats and heels, silk blouses, funky jewelry, bright sweaters, cardigans, and structured totes to classes, meetings, and events. And the more I integrated these pieces, the more I started to notice that there WERE other people on campus who dressed like me; I just hadn’t really noticed them before, because I was so focused on the people who dressed differently.

  28. lisa

    Interesting topic and discussion in the comments so far. For me, “trying too hard” means wearing styles or items that don’t feel authentic and consequently end up making you feel inauthentic. I find this can happen often with trendy pieces since I’m more of a classic/preppy girl at heart.

  29. CC

    It has been years since I felt like I was trying too hard. The last incident occurred in grade school. I went to school wearing a long sweater and long skirt (it was the eighties, ok). Once I got to school, I took off the skirt and just wore the sweater with my white tights. Probably not a good look. I know I got made fun of. As the new girl, I always did. I think I hoped that dressing a little more like everyone else would change that. It didn’t. I think that moment was enough to remind me that I was happier just being myself regardless of what people thought. I think I’m lucky in that I’ve never been too concerned with fitting in. That was the only time I really tried. I was so uncomfortable and still got made fun of. Bad idea. Anyway.
    I work with youth and have spent the last decade reminding them to be themselves and trying to encourage them when they express themselves. It is so important to recognize that you don’t have to be like anyone but yourself. Being ‘cool’ really isn’t as fulfilling as you think it is. It is far more important to be you – whoever that is.

  30. Salazar

    This is such a timely post, because I’m at that point in my style evolution where I’m constantly confused between “trying too hard” and “trying something new.” And I have to admit, no matter how much I say I’m doing this for myself, there’s a part of me that’s always hoping to impress others as well. But I love your advice to “fake it”, because that’s so true. Part of being stylish is to be confident (or act confident) in what you wear.

    On a side note: I was reading through the comments and caught one about Esprit. Don’t people wear the brand anymore here in the US? I have some pieces by them, but my sister bought them for me in Germany so I can’t say…

    • Sal

      Yes! I still love Esprit designs! But when I was 13 the brand had just made it over to the States, and it was THE thing to wear. Like the young teen girl’s version of Prada.

  31. Lisa

    Thank you for doing the live chat today! what a blast… I am learning so much! Changing my lack of clothing style one day at a time!

  32. Megan Mae

    I felt this way times a million when I first started the blog. Comments like “Oh my – why did you get dressed up?” when I decided to wear a skirt or dress instead of jeans killed my self confidence. Nearly two years later my family has adjusted to my “new” look, and I’m now dealing The Voice.

    Sometimes I’ll put on a necklace and earrings, and take one piece off. Sometimes it’s a matter of changing shoes, adding a layer or different belt. There’s a point where “getting dressed” isn’t hard, and I have a handful of possible outfits at my fingertips any day. I may still feel overdressed to go to the grocery, but I feel good and that’s what is important.

    I totally use that line “Isn’t it WILD” or “Isn’t it GREAT” and a big ridiculous grin when people say things now. I love my clothes too much to let other people’s negativity affect me.

  33. Ana

    I think we have all felt this way at some time or another. When pondering these questions, I realized that many times when I felt that way, it is my own demons that made me feel this way and very few comments/looks from anyone else. Sure, if you wear someone very outrageous you may get looks, but I think many times we feel like we are trying to hard when we aren’t feeling quite right in our own skin.

    Think about it, many times I try to hard so I can look good when I am not feeling like I look good. OR I might be feeling like I am trying to hard when I am trying to be someone I am not. While this one can sometimes be positive, I think many of us or trying to please other people or fit into a certain mold when dressing and are not being true to themselves. Lastly, there are times when I feel like I am trying too hard to get some menial thing right about my outfit, hair, makeup, etc. and it really is my chaos in the attempt that makes me feel that I am trying to hard.

  34. Annie

    Thoughtful stuff. In our house we called that “chasing cool” and my children all knew it was a path to nowhere. Not once did one of them ever see where trying to be or do ‘cool’ made any difference, and that was of course because it was a lie about who they were. They were already perfectly themselves and confidence is more cool than anything else.

  35. Fashion Herald

    I bet everyone’s got one of those “chasing cool” moments! (love that phrase too!) Once I wore a tie-dyed shirt in high school and some Deadheads made fun of me for ages. That’s probably why I still don’t like the Grateful Dead πŸ™‚

  36. hillary

    Not surprised that yet again I find myself nodding as I read though. I struggle with the trying to hard and what that means to me and if I feel that I am being me or what i think is cool.

    On an aside. I thought I recognized the picture and I look down at where it’s from and its actually a really good friend of mine!! small world!

  37. masha

    Avoiding the appearance of trying too hard is a fairly central part of my professional wardrobe mojo. But I don’t feel that I have a conflicted relationship with this. The number one thing I try to project with my work clothing is a sense of confidently relaxed competence. I happen to work in a hyper-casual work environment—i.e. the #1 style bylaw seems to be that everyone should be ready to go camping at ALL TIMES. In this environment, looking relaxed and approachable simply requires wearing low-key and very functional clothing.

    Over a long period of time, I have figured out how to meet this casual standard, but also work in a little bit of my own sense of style. I can work in a fair amount of style, so long as the end product doesn’t appear to by “trying too hard.” That is actually my rule of thumb for evaluating an outfit. For example, I can wear a blazer with jeans, or I can wear slacks with a t-shirt. But slacks with a blazer is too much.

    Of course, when I am away from work, I do enjoy the chance to wear something flashy and impractical every once in awhile.

  38. Loren

    When I was younger I was really self conscious about my (I kinda still am at 24). I hate to admit it but in college I judged some girls rather harshly for dressing in a way I thought was ‘trying to hard’ because they had the confidence to wear things that made me uncomfortable (and showed off their bodies). Nothing really ‘risque’ but lots of shirts that showed cleavage, short shorts, tight t-shirts. These girls are now good friends of mine and while they all still appear to be more comfortable with themselves and their wardrobes than I am, they are all wonderful people and so much fun. But I remain the ‘weird alternative’ one. I’m a little more comfortable in my mildy risque outfits but these women still wow me with their seemingly effortless ensembles.

  39. bonnie

    My husband and I have friends who are in a much higher socio-economic bracket than we are. I have frequently had that trying too hard feeling when we get together with them. For instance, I wore a pencil skirt and heels to a dinner party only to arrive and find the other women in sun dresses and flip flops. I ended up feeling awkward and out of place all night, and mumbled some excuse about not having time to change after work ( No one asked. I just felt like I had to explain myself). I think what’s at work at these times is a definite feeling of class inferiority. The funny thing is these people are all very friendly and laid back, and wouldn’t dream of looking down their noses at someone else’s clothes.

  40. Lorena

    I love reading your posts.
    I always relate to them πŸ™‚
    You had me at the line you mention the “Esprit ” assemble – it kinda made me feel we were in the same school.

  41. Amy Beans

    On a related note, this post has hardened my resolve to wear the brightbright blue patent flats AND the yellow flats I just ordered to work. &^% ’em.

  42. Sarah R

    Michelle at 11:58, I totally hear ya. I live in Florida too, and believe me when I tell you that I live in dresses/skirts 90% of the time. And the LOOKS I GET…they can be unreal. From glares from the pajamas wearing curlers-in-hair mamas, laughter from the goth teens wearing all black (in Florida…seriously you’re gonna die of heat exhaustion wearing a trench right now) and then comments from senior citizens who declare how “lovely and sweet” I look. Little girls have asked me if I’m a princess at libraries (and all I’m wearing is a knee length skirt with sandals and a top, nothing crazy) and even at church, I’ve been asked “Why ya so dressed up?” Really? AT CHURCH? It used to bother me, a lot, and then it finally occurred to me that people were projecting their own insecurities onto me. Now I wear my dresses and skirts proudly. I do still get stares, but it doesn’t phase me anymore. I’m comfortable in my look.

  43. Eliza

    I definitely worry that I look like I’m trying too hard at times. I wear a lot of formal clothes, primarily because that’s the look I’m drawn to, but also because tailored pieces suit my body type better. I’m surrounded right now by girls who (for a variety of reasons) tend to have thinner and less curvy bodies than mine. They can throw on an oversized white tunic, leggings or skinny jeans and a pair of sunglasses and look chic. If I try to dress the same way, it really doesn’t work for my body type or personality. Instead, I wear what’s comfortable for me, but I’m very concious that I often stand out stylistically from the people around me, and that I may be judged because of that.

  44. sarah

    so, here’s a great study in contrasts. My husband’s architecture firm just finished a 15 million dollar “remodel.” Kelly Wearstler did the interiors. 2.2 mil in furniture. chaching! There was a catered open house for all the people who worked directly on the project (landscapers, a few members of the arch firm, etc.) to see the finished project (holy MOLY). I’d been meaning to make a copy of the reid peppard winged headdress (a pair of taxidermy pigeon wings on a leather-covered metal headband) that Rumi was rocking on fashion toast last year. This seemed like *the* occasion.

    So I made it, and I dressed up. We ran a couple of errands before and after the open house, too. I drew STARES and double-takes everywhere we went around Seattle (whoa, people! it’s just headwear!). A few people at the open house commented on the wings – positively, though. But here’s what’s funny. My husband’s coworkers? Didn’t even bat an eye. I don’t even see these people all that often, yet they found my ensemble completely normal. It was a nice reminder in the midst of all those looks of how quickly anything can become “normal” if you just own it.

    It also helps to find those SUPPORTIVE friends who are interested in fashion and who will encourage you – especially the ones that will encourage you in your own aesthetic, even if your aesthetic differs from theirs. I have one girl in my life like this, and she probably doesn’t even know how amazing her constant, positive energy is. I’ll show her my gratitude by lending her my DIYed McQueen hat one of these days. =)

  45. Nethwen

    Insightful post.

    The “why are you dressed up” questions really bother me. Where I live, putting on a skirt makes you look as dressed up as if you had on a formal gown, if the comments are any indications. One day, when I had nothing but a skirt to wear, I got so fed up with the questions that I lashed out. Then my mom suggested that maybe when people ask, “Why are you so dressed up,” what they are really saying is “You look good.” I still feel self-conscious when I get the comments, but Mom’s idea gave me a different perspective and more tolerance.

  46. Starfire

    I’m not sure if I’m going through this at the moment or not with the whole “showing off my legs” thing. I definitely feel like I’m out of my comfort zone every time I wear my long-tunic-and-leggings combos into work…

    I keep half-expecting someone to take me aside and gently say “Oh honey, you know you shouldn’t be wearing leggings with *your* legs”… but I guess that’s only to be expected, given that I’ve spent my entire adult life feeling as though I’m morally obliged to hide them away for the good of society! In fact, no-one has yet to say a single negative thing; and I’ve even had some compliments on a couple of the tunics, and one of the pairs of boots I’ve worn (wooohooo! I can fit a pair of non-ankle-height boots! First. Time. EVER. in this country!)

    I’m determined to *keep* doing it though, unless I decide that it genuinely doesn’t look good on me. And if/when I make that decision, I want to be clear that “it doesn’t look *good* on me as a whole person”, rather than “it doesn’t make my legs look slender”, which nothing other than photoshop would manage! It’s hard to untangle those two concepts in my mind, but somewhere deep down, I believe it’s possible – that looking good doesn’t HAVE to equal looking as though I have fashion model proportions – so I’m willing to work at it.

    So yes, I’m definitely *trying* hard with this, because something in my gut tells me it’s worth trying for… but I don’t think I’m trying *too* hard.

    Does that make sense?

  47. Lisa

    I think of trying too hard as meaning stretching one’s style parameters beyond what one knows how to put together. For me, it would trying too hard wear too many accessories, or too eye-catching a get-up. Not that those things are wrong, per se, but for me it would involve trying and failing to pull off a look. That said, everyone should try too hard now and then, it’s the only way to learn, to do new things.

  48. coffeeaddict

    You did it again, Sally! Another excellent post and I got lost in all the comments and got nothing done today πŸ˜‰
    I really had to think hard on this one, but I think I’ve outgrown the trying to hard bug somewhere in my early 20s in college.
    When it comes to clothing, my bug is of a different nature: I hate to wear what everyone else is wearing. I have this need to be unique, not out of vanity but just the idea of blending in visually, stylistically like a herd of obedient sheep makes me shudder!

  49. Bex

    My absolute low point in this sense was a couple of years ago- I am tallish, and I went out for the night with a group of friends in a pair of absolutely KILLER shoes- tan sandals with a good five inch heel that I adore, and fit me perfectly. I felt so awesome in them, as I always do in a fabulous pair of high heels. Then I happened to walk past a group of women and managed to overhear one of them saying to the others, “What on earth does a girl that height think she’s doing in heels? She looks HUGE.”

    Ugh. It really hurt, and I really started to question my love of the heels as if wearing them was, indeed, me ‘trying too hard’ or ‘being something I’m not’. It took a year for me to convince myself that being tall wasn’t a bad thing, or that being five inches taller than my actual height wasn’t a bad thing either. My boyfriend hated the fact that a comment had taken away my love for my awesome shoes, and spent ages helping me get back into my heel love– but it was, ultimately, a fight I had to win for myself. I still feel a faint tingle of insecurity when I strap on my six inch stilettos – but now I fight it with a really good red lipstick and some sass. On the outside, anyway- I haven’t managed to fight the inner Voice as effectively.

  50. Terri Walton

    “Why are you dressed up” questions bug me too. I’ve also had that mental block where I feel like when I am attempting to push some style boundaries, I’m being a “poseur”. Then there was the time I went out to dinner with my husband wearing a grey and black striped dress, black tights, and engineer boots…only to run into a former co-worker who asked if I had started riding motorcycles.

  51. SusieQ

    I live in South Florida where the ‘typical’ outfit is shorts, t-shirt and flip-flops! Although that’s nice and comfortable I want to feel like I’ve actually made an effort. It’s just as easy to throw on a dress, belt and cute sandals. I do think part of me wants to stand out from the crowd and be original, not cookie-cutter, and have my own look rather than that of everyone around me.

    My workplace is the same. Although it is an office people are generally pretty casual (no jeans except Fridays though). But I tend to dress more professional than everyone else – and I’m completely ok with that.

    I believe that clothes and style are a reflection of oneself, so it’s quite important to me to dress in a way that shows that you care about how you portray yourself to the world.

  52. Lacy

    Great post, Sal! Just wanted you to know that you have officially inspired me! I’m wearing a dress today that I have owned for more than 3 years, and never worn. I love it, it fits my body type, and it’s cute…. but I didn’t want other people to think it “wasn’t me”. So today I’m wearing this dress, even though I’m just home with my kids. I’m going to take your advice about dressing up once a week and see how that makes me feel. I’m excited about it! πŸ™‚ Thanks for writing such an inspiring blog!

  53. style odyssey

    Me again. πŸ™‚ I came back to read some of the comments; such an insightful post, Sal!

    Thanks, M. and Pauline, for replying to say that Esprit is still out there.

    I wanted to add something else. The Florida people who commented, I can so relate to “why are you so dressed up?” questions! I lived on a Caribbean island for many years, where the uniform was board shorts, tank tops, beach frocks, and flip-flops (which I liked; I mean the uniform definitely had its place in my wardrobe!) However, anytime I dressed differently (real shoes, outfit), I got some odd remarks, especially “Why are you dressed up?” which to me, really means “Why are you making an effort?” (I honestly encountered people wearing cargo shorts and t-shirts to semi-formal events.) Most of us don’t equate making an effort with trying too hard but that was the prevailing attitude in the islands, as well as Florida, where I’ve also spend much time. It may be a challenge, but it IS possible to dress nicely- without “trying too hard”- but in accordance with one’s environment, as we tropical girls know! πŸ™‚

  54. Audi

    Oh gosh, trying too hard. To me this just smacks of high school cattiness and the most dreaded of insults, the accusation of being a “wannabe.” As if select people are genuine and anyone else who’s drawn to that style is only a cheap copy. Honestly I think all the feelings I’ve ever had of trying too hard have all stemmed from there. It’s utter BS. And to me the friends whose reaction you dread whenever you want to try out something new aren’t really friends at all. That’s a lesson learned the hard way, to be sure.

    At a young age I found it hard to figure out what my style really was, because there was so much outside pressure to fit in. Even as I got older and more secure in my tastes, it still took a concerted effort to shake off that stupid high school feeling of being scrutinized by people who deemed themselves qualified to do so. It wasn’t until after college that I realized I’m the only one qualified to determine what is and isn’t my style.

  55. Jessica

    Sally: Yes, I had exactly this problem. I was giving a presentation for work and I wanted to wear a suit, but the company culture was business casual. I didn’t want my colleagues to think I was trying too hard. My husband, after listening to my concerns, told me to just wear the suit. Wear it. Own it and just don’t think about what others think. I had a realization at that point and I wore that suit and incidentally felt great during my presentation and even got a few compliments on my attire. I was told it was the best talk of the entire conference!! So, I always try to remember: wear the suit!

  56. Alanna

    For me, the issue was always body confidence, especially in my teens. Baggy jeans and baggier band tshirts told the world I didn’t care what I looked like, I didn’t care that I was fat. Totally not true at the time, but hey. I thought “getting dressed up” would mean people could tell I cared about my appearance, that I was trying to look good, but at the same time I thought being fat meant I never actually WOULD look good, so don’t let people know you care!

    Total bollocks. I’m 24 now, still fat, but also good looking (on occasion), and I’m gradually carving out my own style (and actually buying clothes that fit me). Blogs like yours are a big part of this development – thanks for the words, the images and the support you put out there. It really does make a difference.

  57. Cel

    I usually feel like I’m trying too hard if I’m wearing something dressier than I’m used to, in a very laid back casual environment. Even if I feel totally smoking as I leave the house, if I’m wearing a neat, clean, put together outfit I’m happy about, if I wind up around slobbily dressed folks, I might feel like I tried too hard.

  58. lizanne

    I get harrassed at work if I even wear a simple skirt with boots! I get all kinds of comments I feel the need to respond to- the only thing that shut them up was when I said, “yeah- job interview today” but I wish I could wear a skirt every now and then without the attention!