Reader Request: Internal Style Conflicts

What do you do when your dressing preferences clash with expert recommendations for flattering your figure?

Reader Sarah e-mailed this request to me:

I’m short and small-boned and hourglass-shaped, and I can find lots of advice for dressing that body type (full skirts, v-necks, nipped waists, tailored pants, etc.). However, I feel like there’s a clash between my body type and other elements: my face (apple-cheeked, not conventionally pretty), my hair (very short), and my personality (tomboyish, casual). When I wear skirts and dresses, which I do think suit my body, I feel very self-conscious, like I don’t match what I’m wearing. Clothes that I feel more like myself in (bootcut jeans, casual graphic tees) do not make me look my best. I wonder if other women struggle with this type of conflict, and how they deal with it.

In my opinion, this is a very important question. And I’m sure it’s one that many of you grapple with, if not constantly then occasionally. The world is brimming with rules and opinions about what “works best” for your figure type, and in exploring those recommendations you may find that they DO make you look traditionally stylish … but that some of them feel wrong, costume-y, or just plain uncomfortable. There’s no one right way to resolve this conflict, of course, but here’s what I told Sarah:

_ _ _

The “looking your best” you’re focusing on has to do with maxims of traditional figure flattery. As a petite, hourglass-shaped woman those maxims will definitely push you toward v-necks, belted waists, knee-length or above skirts, and lots of traditionally “feminine” silhouettes and garments that will define your figure and balance your proportions. And although those styles probably make you look great by magazine-approved beauty standards, you just don’t feel like yourself in them. And in my opinon? THAT is a far more important consideration.

Looking good can impact how you feel, leading you toward more self-care-focused activities or bolstering flagging confidence. This is why I write about that look good-feel good connection: Because for many women, dressing in ways that make them look amazing can help them unlock positive feelings about themselves overall. But since the socially-sanctioned “looking good” in your situation clashes so strongly with your internal self concepts and makes you feel disconnected from your physical self and appearance, this idea needs some tweaking. That connection works both ways: Feeling “off” or badly about how you’re dressed can really impact how you feel about your body and self. Negatively.

Dressing to conform to traditional style and figure-flattery rules is never, EVER required. By anyone. If anyone ever tells you that there is one right way to dress for your body type, please send them directly to me and I will slap them in the face with a large fish. It is your body, so you get to make the decisions about how to clothe and present it. End of story. OK, not end of story, but Very Important Bit of Story. You have experimented with the looks recommended to you by style experts and seen how those looks affect your figure. But if you feel more like yourself in casual, tomboyish attire – bootcuts, graphic tees – then that is your sartorial home base. And there is nothing wrong with that. As the very wise Erin said so eloquently back in the day, you don’t have to be “pretty.” In my opinion, it is far more valuable and important to be happy, fulfilled, engaged … pretty can help, but it’s very seldom the endgame.

It might be possible to merge the recommended and internal styles a bit. Since you’ve played around with skirts and belts and suchlike, you probably know which of those items really made you feel great about your body and your looks. Can any of those work their way into your home base style? Could you try a graphic tee tucked into one of those full skirts, maybe with a fun belt? Do a fitted v-neck with your bootcuts and a cool pair of oxfords? Maybe there is a sartorial middle-ground to be had.

But there might not be. And that’s completely fine. If dressing in those recommended clothes makes you feel like you’re pretending to be someone you’re not, that just won’t work. Not in the long run. You’ve got to wear clothing that makes you feel like yourself.

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Image courtesy Refinery Shop

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Originally posted 2013-07-31 06:05:30.

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26 Responses to “Reader Request: Internal Style Conflicts”

  1. ParisGrrl

    I spent a good part of my childhood railing against the colors and styles that other people thought I looked pretty in, and it took a long time before I started to feel I really had a handle on what worked for me internally as well as externally. In Sarah’s case, maybe she can try out a few “conventionally” flattering items with her comfort base–like a leather or fabric waist-accentuating blazer with her favorite graphic T and bootcut jeans. Perhaps add some additional bootcuts to her wardrobe in less-expected fabrics like velvet or corduroy for a dressier look without the dress. Or add some bold piece of jewelry or other accessory to jazz up her look. It’s fun to see what the style “experts” have to offer, but I think at the end of the day we should love what we wear, and not have it wear us.

  2. Judy Carpenter

    I’m 68, overweight, and in a similar place. Except my problem is one of styles. I love boho. The best pics on the internet have boho as wearing cut up jeans and mismatched things with a ton of jewelry. I can’t make myself do that. The jeans are out. I can’t wear jeans and I wouldn’t have cut up ones. The ton of jewelry is mostly in gold and not silver. And too much pattern makes me crazy. So far my answer to the problem is boho top, regular pants, fringe bag, and mocs. I’m very comfortable in this outfit type. Relaxed. And when it gets cooler maybe I’ll add more to the look. At 68 I don’t much care about the opinions of the general public and am looking to live time out in comfort with the colors and attitude of bohemian.

  3. AnnR

    I’d give some thought to what “look your best” means to you.
    Do you look groomed, clean, deliberate, at least marginally appropriate/respectful towards the situation? If you can answer yes then you can leave your concerns behind.

    Not everybody wants to approximate the Anthropologie look. Perhaps you’re more Eddie Bauer.

  4. Ry

    I personally was feeling very uncomfortable as I left the house this morning in a button down shirt tucked into a high waisted pencil skirt. Being 5’10” and fairly thin, I always get compliments when I wear similar things to the office, but I don’t feel like ME in them. I’ve struggled trying to find office appropriate pieces that I actually feel comfortable in. Things that don’t bunch up and wrinkle and feel tight in all the wrong places. 😛 Just give me a pair of black leggings and an oversized cardigan.

  5. Pretty pink

    This is such a great post and such an important question. Yes, I do struggle with this well. I am petite too (4, 11′) and have a big round face with apple cheeks which means a lot of things that look good on my body don’t quite mix with my face. While blazers make me look really good I feel very formal and uptight in them. Colorful statement necklaces can really pull my outfits together and they photograph so well but every time I wear them I feel heavy, huge and simply BIG. I stopped wearing them all together. On some occasions I still dress to look rather than feel but increasingly rarely !

  6. Lianne

    This could have been written by me. For much of my life, I just wore what I liked and ignored the style/flattery issue altogether. But recently I’ve been discovering that there are things I can wear that both suit my body AND my personality – cool jackets, belts that make me feel like a pirate, generally stuff that’s boyish in style but cut for curves plus just a hint of costume/dress-up – and I’ve been liking doing that. In fact, since I’ve started thinking about this stuff, I feel like a lot of the things I’m wearing are MORE ‘me,’ whereas before I was just defaulting to a kind of generic tomboyish uniform because I didn’t know that there was anything other than feminine clothing that could be stylish and fit my body.

    By the way, I actually think well-fitted boot-cut jeans tend to be really flattering on hourglass types! If you’re very hourglassy, you might need to get them taken in at the waist to fit well, though.

  7. Elizabeth Ann

    It might be helpful to remember that even when a particular item is the “right” or “wrong” one for your body type, fit still plays a major role. Boot cut jeans might be “wrong” for you, but properly tailored boot cuts are still going to look 100 times better than an ill fitting full skirt that hits you at an uncomfortable spot. If graphic tees and boot cut jeans make you feel good, think about investing in the perfect ones (or having your favorites tailored to fit in a flattering way). If a particular style or item is what makes you feel good, find a way to make it work for you rather than against you.

  8. Hannah K

    Awesome post!! One for the Sally highlight reel.

    (Plus what Lianne said–you can get any old style in a *shape* that “flatters” your figure.)

  9. dustwindbun

    This is definitely how I do things. I don’t feel like I can see myself accurately these days to actually judge what “looks good” because to my eye everything looks bad! So rather than feel bad about it I just stopped looking. (I mean I check for, is my hair sticking up inappropriately, is my skirt tucked into my underpants, how much cat hair am I wearing, and such, but I don’t look at “does this flatter me” any more. Aside from colors. Colors I can still see.)

    I pick out outfits and pieces that make me *feel* like I look good. I’m 5 feet tall and built like one of those ancient fertility idols (big shoulders, hips, and bust, and a round tummy poking out in front but small-waisted when seen from the front, if that makes sense). By fashion rules, I shouldn’t wear anything long, or capri pants, or tunics and leggings. Yeah, forget about that. I am a devotee of long duster jackets (I think of it like TV Tropes refers to them: “Badass Longcoats”), boots, gauchos, tunics, Danskos with anything, bracelet-length sleeves, and bright colors. I only wear “accessories” other than scarves on special occasions because I don’t like dealing with them. I don’t wear makeup outside of special occasions, and I don’t “style” my hair (both due to lack of patience/desire to sleep in even if it’s only for 30 more seconds). And I have no problem with horizontal stripes!

    I admit I’m privileged in that I’m young enough (31) and attractive enough to be unremarkable so I have an advantage there in doing what I want. Plus I already have a good job and a partner, so I don’t need to find one of either, and my partner lives two states away so I don’t “need” to dress up for him every day either… But I do find that things that “shouldn’t” be flattering on me often get positive reactions from people, and I have to think the only thing that’s changed is that now *I think* I look good!

  10. Kat

    I sort of disagree that if you feel self conscious and costumey in a different style of clothing than you usually wear it means you are stepping away from ‘your style’. If your making any sort of big change (like t shirts and jeans to skirts and fitted things), of course it’s going to feel different and odd for a while. If you don’t have the best self confidence or body image, then *you* noticing the difference in your appearance is going to translate to *everyone else* noticing it to, making you even more self conscious. Which isn’t help by the fact that if you change like this around people you know, they are going to comment on it, and even if they are positive comments, it’s someone noticing.

    I say this because it happened to me! I wore nothing but tshirts and jeans for twenty+ years, and then i spent four months with my boyfriend in another country. We talked about how I didn’t care for the way I looked and made the decision to bring only one pair of pants. I lived in skirts and dresses and worn those pants exactly once, and while I felt super weird at first, i got used to it and enjoyed it after a while. When i got back home, there was a readjustment period of people noticing me wearing a totally different style, and of being slightly dressy when most people weren’t, and I felt self conscious all over again. But in the end, pretty much all I wear now are dresses and skirts and it feels more comfortable than my jeans every did.

    Now of course this isn’t the case for everyone, and I had always wanted to try wearing the things I do now, but felt too nervous and weird when i did to keep trying. Why are you trying to make the change in clothes? Is it because you are curious about the other style, or have a desire to look that way in the back of your head? Or is it because you feel pressured into it or fell like it’s the ‘better’ thing to do?

  11. BethL

    Excellent post!! How you feel in clothes, if they are “you”, is so important. For example, I do not like suits on me. On others, they work fine. If I wear a suit, I feel and look like a “fraud”.

    Sally’s is the best blog out there. 🙂

  12. Annabeth

    What I would say is, try to synthesize the silhouette and the mood. OK, a conventional skirt and sweater don’t work for you — but what about an edgier plaid, denim or leather version, paired with your favorite graphic T, crazy tights and Converse? That way you might rock the hourglass silhouette AND have the more casual feel you crave.

    This is, of course, when you’re hoping to maximize conventional figure flattery. When you’re not fussed with it, then wear what you like and have fun.

  13. Halo

    Sally’s advice is great. It makes me sad when people think they shouldn’t wear something because it’s not “flattering” or that they’re boxed into certain things because of body shape.

    Before reading this letter, though, face shape has NEVER crossed my mind as a consideration about personal style. Hairstyle and glasses selection, sure. But clothing? Am I missing something? This is an honest question, because it seems like any face should go with any style.

    • Sally

      Halo, I think face shape becomes a worry for some women – like Sarah, who feels her youngish, apple-cheeked face clashes with her preferred style – but agree that it doesn’t loom large on most figure-flattery priority lists. At least, I hope it doesn’t!

      • Halo

        I guess I’m just not at all computing what it means for a face to clash with a style. I also hope most people don’t give it much thought!

        • Sarah

          Hi Halo! I’m the Sarah that sent Sally the question. The big conflict for me is that my face is not pretty, which makes me feel odd in clothing that is. Because I have a very feminine figure but not a feminine face, it feels like a mismatch. Maybe most people don’t think of it, but it’s a problem for me.

          Thanks so much to Sally for posting my question, and to everyone for your responses!

      • Lynn

        I think it may for some of us. I had a heart shaped face for many years, but have aged into a squarish one. To me, it makes my clothes look different. Heart shaped seemed to go with curvier clothes while the squarish face fits with more geometric styles.

  14. Aya

    I too am short, apple-cheeked, and most at home in bootcuts! There are a number of conventionally nice styles for short women that I appreciate on others but would not ever choose to wear, such as the blazer/cuffed skinny jeans/heels look. My family thinks I look best in tailored shirts and slacks, and I think it’s too boring for me. They find my fashion choices weird, but accept it.

    My personal opinion is if you choose clothes that fit you well, in the styles you enjoy and feel rocking in, people will notice and compliment your style. A big one for me is getting bootcuts short enough that they are still bootcuts when I tailor them, and getting the waists taken in on everything, ’cause I’m broad-shouldered.

    And at least for me (I’m not saying this would necessarily be for you) I enjoy some costume-y elements mixed in with my style, so long as it doesn’t take me too far from home base that I feel physically constrained or uncomfortable. I favor boho type ragged hems and bits of lace sewn on and goth/punk mermaid skirts (I think of it as the skirt version of bootcut)

    I think guidelines are great in that they are merely guidelines. They give us information that we can then make informed choices on, such as whether to follow them, or ignore them entirely if they don’t work for us.

  15. Gracey the Giant

    Wonderful question and wonderful post. I struggle with this as well and some days have to try very hard to remember to add something to my look that is me (well, the me I am that day) because it helps me feel comfortable.

  16. SKP

    Yup, this is my problem too – having an hourglassy “super-feminine” body shape, but preferring more “boyish” (or gender-neutral) kinds of styles. As a teenager I just wore men’s clothing a lot, but it got to feel so awkward and lumpy. For me, there has turned out to be a middle ground. It consists of clothes that are cut to follow curves without overemphasizing them, and that have less-girly colors and styling.

    Traditional figure flattery advice has been somewhat helpful, but I also credit Sally for her posts about figure flattery priorities and about considering the specific optical illusions that are created by specific aspects of clothing. It gives you more options than just “wear full skirts”.

  17. Erika

    This really resounded with me! Grew up predominantly in jeans and flannel shirts (farm), stayed like that through early adult years. Have played about with dresses and skirts. Got depressed, wore black for years, gained weight. Lost weight, went on meds (other side effects) and started enjoying clothes again. Yep, there is an hourglass under all that fabric I was hiding in.

    What I found really useful in the experimental phase was thrifting and ebay. Sure, I picked stuff that looked good on me, but didn’t feel right. So passing it on doesn’t involve major financial woes.

    I’ll happily wear skirts and dresses these days but I still tend to jeans. And I still buy mostly off ebay. It’s the only way I can afford Vivienne Westwood!

  18. Erika

    Oops – forgot to add – if you want a femme edge, use makeup. I’ve just discovered bright lipsticks (47, what can I say, slow learner) and they immediately take you out of boy-territory.

    And weskits. LOVE the effect waistcoats have. They can nip in the waist AND provide a level of warmth over the back.

  19. Sonja

    Okay, so I still haven’t read through all the comments above, but I’m just itching to say something about this.
    I have been in a very similar situation a couple of years ago, because I’m petite and hourglassy as well (although well-rounded), and I had been a tomboy my whole life. I started to experiment more with clothing and style, have learned to walk in heels and have now as many skirts as trousers (maybe more).
    But – and here I agree totally with Sally – you don’t have to wear any of these things if you don’t want to. And I think, as she and some of the commenters have said above, this is true on several levels. First of all, you can wear whatever you feel comfortable with. As long as you look minimally appropriate for work and social events, do whatever you like.
    Second I would like to say that even “tomboyish” clothes can be flattering, if that is important to you.
    Bootcut jeans balance hourglass-hips beautifully. Simple tees can show of your waist if they are fitted, and flatter your face if they have a deeper neckline (crewnecks won’t do that, as I’ve learnt here on Already Pretty).
    A short, fitted moto-style jacket will emphasize your waist and bust. Shorts that are fitted around the butt and end at the knee will look as flattering as pencil skirts. Etc, etc.
    You can also work with colours – darker colours look more elegant and flattering, also a bit more powerful and masculine. In my opinion, a dark wash jeans with black sneakers and a fitted black tee will look more put together than a similar outfit in lighter colours.
    Personally I think I’ve now definitely left tomboy territory, but my personality is still similar – I have a mind of my own, can sometimes be bossy and opinionated, I like to know how things stand, and I like my clothes to show that. One of my biggest fear is to come across as too soft and feminine, so I like to create a balance within my style. If I’m wearing jeans and sneakers, I might put on some make up to soften my features, but with a floral dress, I might wear a spiky, rebellious hairstyle. I also tend to chose strong, saturated colours to show that I don’t like to do things by halves.
    Maybe that helps a bit?

    • Mollie

      Sonja, you captured my thoughts as well…especially wearing saturated colors for the all or none 😉

      Many great ideas, I have only one to add: boots! A few years ago a got a pair of tall black moto boots and they were the savior to this dilemma for me. I can wear a dress or skirt in a cut that makes me feel good about my body (but no feminine details–no lace, no ruffles, etc.) and add my moto boots and feel tough and strong and able to run and kick things.

      I still struggle sometimes, but this conversation has made me think that balance might be the key, b/w masculine and feminine elements for example.

  20. ModernSauce

    Great question and super great response, Sally! I love what you said about merging the two styles and finding a middle ground. Those “expert” style rules in the mags only work sometimes on me and I had to spend a lot of time figuring out my personality first and THEN see what looked good on me and what I felt good in (which also helped further define my clothing personality).

    I’m boyish/apple-ish in my body but have a very feminine face (if that makes sense) so sometimes trying to make my body look more traditionally feminine like style guides would suggest felt weird and sometimes just looked TOO feminine for my personality/body. But I found that if I dress more “masculine” – blazers, structure, dark colors – that it highlights my other ultra feminine qualities (lot of makeup, shiny accessories, heels) by contrast. Feels more “me” too!

    BTW – don’t know if that was a Frogman reference or you also slap people in the face with fish but it made me laugh either way. ; )