Dressing for Yourself and Dressing to Put Others at Ease

It is not your job to  dress in a way that  makes everyone  in your social circle  feel completely  comfortable.

A few months ago, I met with a client who was working on several self-consciousness issues. She was a tall woman, and had to endure an endless stream of height-related commentary from friends and strangers alike. Her mother had instilled in her the belief that her ankles and feet were huge and unsightly, and was struggling to make peace with that. She loved fun clothes and dressing up, but lived in a community where folks attended just about every event from “night at the gym” to “night on the town” in the same casual, comfy duds. We talked at length about this last one, and she said, “I have one friend who I’ve never seen in anything but a fleece and jeans. I wouldn’t want to head to a girls night out in a frilly dress and make her feel uncomfortable.”

And I stopped her. I reminded her gently that it was not her job to dress in a way that made everyone in her social circle feel completely comfortable. In fact, I pointed out that to attempt such a feat would be to set oneself up for failure! We cannot constantly anticipate the feelings or predict the needs of others. We have no control over those things whatsoever, no matter how hard we may try. To charge oneself with dressing in a manner that puts all others at ease would mean sacrificing any hope of self-expression, not to mention the infinite frustration of guessing at how friends and strangers alike might react.

Now, I DO believe in dressing as a social act. Wearing traditionally appropriate attire to important, career-related, and socially focused events can help make interpersonal communication and understanding more effective. And I also understand that being the one relentlessly dressy, unfailingly casual, or just plain different dresser in a group with set practices can cause friction and strife. Furthermore certain social circles have more unwritten rules than others, and dressing is often in the bylaws. I am not saying that you should wear what you want absolutely everywhere and under all circumstances and expect total respect and acceptance from everyone you meet. That’s not how our society currently functions.

But I think it’s important to acknowledge that social pressures to conform – especially among friend groups, and especially when it comes to dressing preferences – can feel restricting. If you show up for girls night in a dress and your fleece-wearing friend feels uncomfortable (or vice versa), that will be awkward for both of you. But is it your responsibility to manage your friend’s response by changing your behaviors? Why? It’s very possible that she is reacting to how your choices make her feel about herself and her choices. You may have made her feel underdressed or overdressed, which many people connect to feeling socially underprepared. You may have done something out of the ordinary that caused her to worry about social balance within your friend group. You may have reminded her of another person in her life that makes her feel uneasy through unexpected choices. Regardless, it’s her feelings about herself, her place, her role, her appearance, or any number of self-focused things that are coming to the fore.

And that’s no judgment call on her! Change is unnerving, and when someone looks or acts differently than we expect, we cannot help but feel surprised and caught off guard. And if a friend shows up looking drastically different from you, that can feel upsetting and cause anxiety. But that doesn’t mean that one person must change while the other holds her ground. Finding ways to open up discussions, make compromises, or work within multiple people’s comfort zones can go a long way. And if, in the end, you choose to change your dressing choices to alleviate social friction, that’s totally valid. In some cases, it’s just not worth standing your sartorial ground. But remembering that it’s not your job to soothe everyone, dress for everyone else’s comfort, or anticipate everyone else’s dressing preferences can feel liberating and allow you to gently push at some of those social boundaries.

Your style job, as I see it, is to dress in a way that makes you feel comfortable, powerful, and like your best self. Your style job is to find clothes that celebrate your body just as it is, and make you feel gorgeous, luminous, and unique. Your style job is to dress for YOU.* And that can be challenging enough without tacking on the preferences and expectations of everyone around you. You’ll have to tweak your look on occasion to accommodate certain social expectations, and you’ll actively choose to do so on others. But I would encourage you to focus on your own desires and preferences as often as you can, and think as little as possible about which people might be made uneasy if you dress up or down, if you choose a skirt or jeans. It’s admirable to want those around you to feel at ease, but it’s not your job to dress for their comfort.

*Assuming that you can. Some of us work in uniforms, some of us deal with strict dress codes, some of us have severely limited budgets … there are countless factors that may actively limit what you can and cannot wear. It’s a privilege to choose to dress for yourself, and not everyone has that privilege.

Image courtesy Nordstrom

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for alreadypretty.com. See Already Pretty’s disclosure statement for more details. Sustainable options are either used, handmade, made in the U.S., artisan made in non-sweatshop conditions, or made using sustainable/fair trade practices.

Originally posted 2013-02-18 06:32:24.

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30 Responses to “Dressing for Yourself and Dressing to Put Others at Ease”

  1. Heather

    It’s funny you bring this up. I have changed my wardrobe a lot recently because I have a portacath in my chest and I have always favored low v-necks and scoop necks before (I liked to show off my clavicle). I feel like making other people comfortable and being self confident are often tied to each other. With the portacath, low necks draw attention to my bandages instead, prompting people to ask questions about whether I’ve had heart surgery or if I’m “OK” — and THAT makes me less confident. Sometimes I wish that people could accept a little more variation, though, and be less nosy about their discomfort. So I have a bandage. Maybe I offer you some collar bone and cleavage with it?

  2. Jill

    Wayne Dyer tells a story (a teaching lesson, when he was a grad student) I’ve never forgotten:

    The self-actualized person shows up at a dinner party. Everyone at the dinner party is completely dressed up. And this person’s in faded jeans and a tee shirt. What would he do?

    The answer: He wouldn’t notice.

    I can’t imagine that I would ever get to that point! 🙂

    Kind of an extreme example, and it doesn’t mean that I don’t try to dress appropriately for specific events (wedding, etc) but most of the time, I’m simply dressing for me. Not to make others feel comfortable. 🙂

    • Anna

      With all respect to Wayne Dyer, who might well have been exaggerating to make a point, it strikes me that the person in this story, who “wouldn’t notice” (really??) is “self-actualized” at the expense of being unobservant or insensitive toward others.

  3. Lynn

    I love this. As a faculty member at a large university, I have colleagues who dress bady on purpose to show that they are too cerebral for such concerns and who sneer at those of us who want to dress professionally. I’ve given up caring, but some of the younger professors who need these colleagues’ support for promotion feel as if they are in a bind. I will send them this article and tell them to please themselves!

  4. Lark

    As someone who is an anxious person, I have to wonder if an important lesson here might be “teach yourself to assess realistically the possibility that your friends will be upset about your clothes”. I know that some people’s social circles can get pretty unpleasant – or at least, so I’m told! – but as a broad generality, I’ve never encountered an adult circle of friends where mere sartorial nonconformity was a cause of actual discomfort and ructions. A little commentary or a little ribbing, maybe – but that was always the flip side of compliments in circles where people actually noticed what others wore. On the other hand, I know that I can work myself up into fits of anxiety about how I talk, dress, etc and truly believe that some innocuous shirt or mannerism is going to cause a problem. Talking myself down from that is a very useful skill.

    As a faculty member at a large university, I have colleagues who dress bady on purpose to show that they are too cerebral for such concerns and who sneer at those of us who want to dress professionally. I’ve given up caring, but some of the younger professors who need these colleagues’ support for promotion feel as if they are in a bind. I will send them this article and tell them to please themselves!

    I work at a large university…not as faculty, alas. In a previous job here, I worked with people who dressed very, very casually (which was a boon to me, since a mere nice sweater and cotton pants that were neither cargoes nor jeans meant that I was the dressiest person on the floor). Perhaps the younger colleagues could take note of what the older ones wear and incorporate elements into their own dress? (I read about this as a sales tip in an old, old copy of Dress For Success and sometimes use it.) So if the older faculty wear jeans and a polo, perhaps the younger ones could wear dressier jeans, nice shirt and jacket? Or a nicer polo-like shirt and chinos if they don’t like jeans? Or if the older faculty tend to wear a particular casual color palette (lots of olive cargoes, for example) perhaps the younger faculty could incorporate those colors into a slightly dressier scheme? It might be worth looking closely at what the older faculty wear, too – what messages do their clothes send? Are they “cerebral” like lab researchers (polos with embroidered molecules, cargoes, jeans, fleece) or “cerebral” like the philosophy department (very disreputable suitjackets, oxfords that have seen better days, cracked old shoes once made by a fine maker)? The younger faculty could perhaps replicate the message but in different clothes – lord knows there’s enough molecule pins, virus ties, backpacks with equations on them, etc to mix up with dressier clothes, and of course all you’d need with the old-tweeds set is newer tweeds. The take-away would be to reinterpret what the older faculty wear so that the older faculty feel that the younger faculty are just the “crazy kids with their nutty styles” rather than people who don’t get it.

    Happily, I’ve never worked with faculty who let their opinions on someone’s fashion sense get in the way of their opinions about the person’s work, but I suppose it takes all kinds.

  5. Brigitte

    I have a slightly dressier than average every day look than most of my friends (little jackets over t-shirts instead of sweaters; dresses and skirts instead of jeans; lots of jersey dresses with coloured tights; chunky jewelry), and while it used to be commented upon (“You’re looking fancy; are you going some place?” “Of course! Meeting you for coffee, silly!”; “Do you honestly wear this when you’re just working from home?!”; “If I’d known you were dressing up for dinner, I would have made more of an effort!”) I think for most of them now, it’s just how I dress and it goes without comments most of the time. But I know it makes some people in my circle of friends uncomfortable, and I don’t always know how to react when they make comments that are not exactly friendly. There was the request that I not wear a dress to a backyard BBQ (I wear dresses pretty much every day, but for a BBQ, I probably would have paired a jersey dress with comfy legging and flat sandals- I had to fish out jeans for the back of the closet, and just felt resentful that I was the only guest being told what to wear, really.), and there’s the passive-aggressive remarks, sometimes, from other women whose husbands have made comments to them about how nice I look and why can’t they (the women) dress up more like I do; these women then turn back to me to tell me to cut it out and not dress up if their husbands are going to be around!

    I just don’t know what to say to that. I don’t dress to make other women’s husbands notice me, but I do dress so that I give the best impression of me to everyone I meet, and that includes these women and their husbands. I’m not dressed provocatively, I’m not showing tons of cleavage, I’m just wearing pretty clothes in pretty fabrics that fit my body properly. I dress so that I like the shape of my body in the mirror when I’m alone at home, I dress the way I do because my husband find me attractive in the clothes I chose; I dress the way I do because it makes me feel confident that I’m looking my best. So what do I say to people who take my clothing choices personally?

    • Mary

      I’m interested in the answer to your question as well Brigette. I can’t claim that the scenario you described has happened to me a lot but I am currently making a shift in my wardrobe choices from jeans/tshirt/casual shoes to include dressier tops shoes and *gasp* dresses. Your comment made me realize I am not prepared at all for any potential comments on my new clothing choices.

      • Sally

        Brigitte – Oh lady, I’m so sorry to hear this. How stressful and confusing for you. This post about dealing with clothing commentary might be helpful in some instances: https://alreadypretty.com/2012/04/clothing-commentary.html

        But wow, I’m wondering if it’s time to have some heart-to-heart conversations with your friends. Either one at a time or in small groups. These women are feeling threatened by your dressing choices – and my guess is that ties into their own insecurities – and putting the onus on you to make that right. If it’s at all possible, I’d recommend talking to them and telling them what you’ve said here: You dress for yourself, it makes you feel good about yourself, it’s important to you, you are NOT doing it to make anyone else feel upset, being told what you can and cannot wear makes you feel miserable. Tell them this ties into your confidence and self-image. I hope that, confronted with that fact, your friends will want to support you in your decision to have fun with style as you feel works best for YOU. (Really hope.) Be gentle and as non-judgmental as possible, but firm, too.

        Mary, the post might also be helpful for you, since you’re in transition now and preparing for possible reactions.

        • Brigitte

          I remember that post, and it was helpful! I think close friends just don’t care, but it’s acquaintances that are a big trickier to deal with I find. They are the ones who may not realize the way I dress when they see me at events (even casual ones) is just the way I dress all the time, and hence the comments. But I agree that it’s a reflection of them and not of me. If they feel bad because they perceive that I have “made an effort” and that makes them feel bad (that they didn’t maybe?), well that’s not on me, that’s on them. I don’t really owe them justifications past “I dress to put my best foot forward.” It’s just my own discomfort in saying this out-loud sometimes, as it can sound a little condescending, like I’m saying “Well, _I_ chose to dress to put my best foot forward, not my fault you decide to present yourself dressed in rags!” Do you know what I mean? But again, if someone wants to read offense where no offense is meant, there’s not much I can do but move on to someone else at the party!

    • f.

      Brigitte, that sounds really hurtful. I am surprised that your friends are putting so much weight on your clothing choices! It’s really sad but sometimes people who we’ve always thought were our friends, turn out to not really be as kind as we had hoped. Just know that you don’t deserve this and it’s pretty unfair for people in your social circle to treat you that way, just because you like to wear dresses!

      • Brigitte

        To be clear, it’s not exactly friends, but acquaintances, these women we all know who are friends of friends, or just part of the same church or clubs we are, and who may not know us as well. New friends may comment once, but not in a hurtful way, and as we see each other more, they realize it’s just how I dress and they just don’t notice anymore. So the weird comments are really just from acquaintances.

    • Anne

      Hi Brigitte. I’ve had a little experience with this too. Most of my friends have known me long enough to know that I am who I am and I wear what I wear. My truest friends are somewhat like minded. It’s those peripheral folks:soccer moms, moms at the kids’ school events, and the occasional relative that seem compelled to make comments. It always cracks me up, why are you threatened by a skirt? I have all sorts of breezy replies. I have had those little conversations with men as well. I tell them, “You wife is lovely as is, she can go shopping with me anytime but really, aren’t you glad that she’s hasn’t picked up such an expensive hobby?”

      • Brigitte

        Anne, I agree! Those are exactly the types of women- the acquaintances, the peripheral peeps who just hang around knowing me superficially and decide that a cute skirt is all I am and feel it’s ok to diss me based on it.

        • Anne

          My favorite response is, “I just needed a little pretty in my life today.” Who can argue with that?

          Also, as it happens, I have a mixed media painting in my bathroom that says, “Wear more skirts.” It’s a mandate right?

          • LK

            I get this from people too sometimes. I only experienced things as harsh as you have in high school where my girlfriends didn’t want me to meet their boyfriends etc because of how I dressed and I was trying to “steal” them. Please! I do get it from my friends from time to time that my clothing choices make them feel uncomfortable. I’m overdressed and I’m petite. Its the petite part in the fitted clothing that seems to upset them ,especially swimsuits. They are not petite and I have been told that sometimes my clothing choices make them uncomfortable and feel bad about their body. But I don’t really think its my responsibility to make sure my clothing doesn’t make them feel bad. Though I will never wear a bikini again in their presence! Not worth the glares!

            • Brigitte

              It’s sometimes similar in my case, but for a different reason: I’m actually plus-size! I know the fact that I look attractive and sexy, not in spite of my size or because of it, just because of who I am and how I present myself is something many women can’t wrap their heads around. Especially fellow plus-size women who have used their weight as an excuse for not making an effort to find flattering pieces, being in a state of mind of “Why bother?” because of a number on a scale or on the back of their pants. It’s like my wearing a cute outfit is an affront to their person somehow.

              But I can see it’s confronting maybe to think of yourself as unworthy of cute clothes and well fitting sweaters because you’ve gained weight since college, only to show up at a coffee morning to meet this new girl who’s probably a good 40lbs heavier than you and looks slimmer because of the cut of her clothes and more put together because she’s got cute jewelry on and some cute ballet flats instead of sneakers. Instead of thinking “Well, I should be able to put that together!” I think a lot of women just think “That b*tch! Who does she think she is?!” It’s not even most women, but it’s definitely the vibe I get from some of them.

              • Anna

                Brigitte, I have been following your post and all the wonderful responses since you originated it, and I have to say that I admire your attitude and your articulateness tremendously, along with your nuanced insight into yourself and the people you meet. Now, the discovery that you are plus-size, like me, gives me further encouragement to amp up my own style a little more (which I have been doing slowly all along as a visitor to this site). You go, girl!

              • LK

                LOL I love your response Brigitte. I think you hit the nail on the head. I’m also a good 4-6 years younger than my girlfriends which doesn’t help. But you strut your stuff and look fabulous! All sizes can be beautiful, I wish women would learn that.

  6. sarah

    I love this post, Sally! I think it’s also useful to point out that if your client began to dress in a way that pleased her, that it would not be long before this style of dress became established as “normal” for her. Sure, people will comment, but eventually, they’ll settle down. Your friends will reorganize the way they think of you, to include the attribute, “dressed up.”

    As for the “why are you so dressed up?” question, I always found that honesty was my best friend. When I finally gave myself permission to wear all the pretty things that had been hiding in my closet, I would answer this question by informing people that, “This is how I always wanted to dress, so I’m trying to finally make use of these clothes that I always wanted to wear!” I never heard a negative response to this – ever!

    • Lizzi

      That response is fantastic, and I’m going to file it away for myself, because I’ve been trying to update my look lately, and while I’m lucky that I’ve gotten mostly positive responses to my efforts, I’m still struggling with the occasional “all dressed up” remark, because my old look could best be called “outdated college student laziness”…so *everything* seems dressy compared to that.

  7. Jessica

    I am getting more comfortable with being the dressiest person in my group of friends. I mentioned to my husband Saturday night that I was going to be slightly overdressed for our dinner outing compaired to the other wives. He quickly told me to wear what I wanted to wear – a beautiful red dress (It was Valentine’s day !!!) and the pearls he had given me for Christmas. There were comments made… but thanks to hubby’s encouragement I was fine. Next step is to not worry about it in the first place.

    I love the response that you’re wearing the pretty things you’ve always wanted to wear. That is SOOOO true for me.

  8. Shaye

    I’m often overdressed, and most times it doesn’t me. But one time a friend and I were going to the roller derby, and we made plans to dress up at our most rockabilly. I showed up dressed to the nines, and she was in shorts and flip-flops – she just hadn’t felt like dressing up! Which is fine, but I wish she’d TOLD me. I wanted to immediately go home and change, but then I was made to feel that my discomfort was putting a damper on everyone’s fun. I stayed, in what ended to being a ridiculous get-up, and eventually had fun, but never lost that vague sense of unease.

  9. em

    I’m someone who dresses much “nicer” than my family, social group, and community (they’re in ultra casual, rural wear and I am just several steps “up” from that). I have to wear what feels good to me, and if I had to wear the things they do, I think I would end up having depression, seriously. When the differences are occasionally more noticeable than other times, I will make a couple of self deprecating but happy types of comments, to hopefully put everyone at ease. Because I am usually the oddball, I think they feel comfortable as long as it’s established that I am NOT judging them in any way.

  10. Cléo

    First, I want to hug your client for being such a generous, thoughtful person! In general, I agree with you that it’s not “her job” and that dressing for others should not come at the expense of dressing for oneself, but I also think it’s a lovely gesture.
    In her situation, it sounds like the situation has been going on for a long time (under-dressing, I mean), which might now be understood as the unspoken “agreement” when she goes out with her casual friend. Rather than suddenly switching and upsetting a balance which is no longer desirable, it may be worth warning this friend in advance (“I cannot wait to show you this cute dress I just bought,” or just “I’m feeling a bit fancier lately, I will probably dress up a bit tonight” would work, right?)

  11. Leiah

    I work from home, and have had numerous comments like “you’re so lucky you don’t have to get dressed up every day!” or “well it doesn’t really matter what you wear, right?” or “you don’t even need to shop or think about clothes since you work from home!”

    I understand some people wish they didn’t have to worry about getting dressed up to go to work, but it’s so strange to me that people expect me not to care about my appearance because I work from home! Usually I tell them that I *have* to get dressed every day instead of working in my pajamas, otherwise I just can’t be productive! 🙂

  12. Kristin

    I’m almost always overdressed compared to my husband, but for the most part, he’s never said anything about it one way or the other. Otherwise I usually fit in fairly well with whatever group I’m with or for whatever the occasion is. Now that I’m working to revamp my style, I expect I’ll probably be hearing more comments in general from the people I interact with and I’m trying to mentally prepare for the ones that won’t be quite so glowing or complimentary.

    It’s funny though, as anxious as I can get about some things the thought that my clothing would make someone else uncomfortable or feel bad about their own choices doesn’t usually occur to me. I want to look nice, but I also want to be comfortable and happy so I wear the things I like to wear. I’m just trying to experiment and broaden my horizons now 🙂

  13. Sue K.

    I live in a small Midwestern town. The standard attire consists of jeans, fleece and tee shirts. I’m simply not comfortable dressing like that. When I was a teen I was always the first to wear what ever fashion trend was up and coming and I never thought anything about it. I didn’t judge the others who weren’t interested in that sort of thing, I did it for myself. Now that I’m looking down the barrel of 50, I notice the same thing. I’m dressing more for myself and I don’t even notice if it has an affect on others. I don’t judge them for what “works” for them and I don’t expect to be judged for what “works” for me. I often find that even though I might be the only one to wear something, soon my friends are jumping on the band wagon too. For instance, a good friend who dresses rather plain commented on a simple but large scarf I was wearing, the next time we went out, she too was wearing a generous scarf (which looked great). Quite honestly, perhaps being worried about making others uncomfortable is more about what might be going on in your own head and not your friends. I mean, there’s a reason you decided to change your way of dressing, search your heart and be sure there’s no judgment for the others who haven’t made that decision. Please, I don’t intend to be mean, I just know we are all human beings and we all have prejudices even though we don’t want to. Dress for yourself and don’t let what others might or might not be thinking worry you.

  14. RM

    This is something I think about a lot. My family and friends have FINALLY gotten used to the fact that I prefer dresses to jeans and shorts. Often I would hear, “Well, if I’d have known we were dressing up for dinner…” or “You’re so dressed up!” For years I just told them the truth, that I find dresses way more comfortable and flattering to my figure. Now I am trying to do more with accessories, and again: I put on a matching belt and shoes, that’s not over-dressed! I honestly often tell people that I’ve come from another event or have another one to go to just because I get so tired of the, “Why are you so dressed up?”

    The thing that bothers me is that sometimes people say I’m “trying too hard.” For years I have worked on a farm, on trails, or as a PE teacher. When I get home from work, I often put on something more “me”; i.e., a dress and accessories! It feels like “trying” to wear farm clothes and track suits! I just wish people would stop putting their insecurities on me, because as secure as I am, it does start to build up and make me feel less secure.

  15. Hope

    I am so glad to have found this conversation! So glad to have Brigitte and others share their stories. I have a new job and a co-worker who reacts to me negatively for no reason I could think of, and my supervisor confided that it was likely due to the way I dressed and presented myself. Although I am nearly 50, I was bewildered! This was outside my experience.
    See, I grew up without enough money to buy fashionable clothes. I have worked hard all my life and am now able to afford to look nice. Last year, during a period of self-employment, I undertook a self-study of style by reading this blog and others, and using that information to learn how to dress myself well.
    It feels like a triumph to me. Yet, with this gift of confidence and the celebration of my emerging style comes the backlash from — I hate to say it — other women. Or, at least this woman. For about a week I thought about what I put on in the morning in terms of whether it would annoy this co-worker. Then I realized how awful that was. I’m not going to say I have totally stopped caring, but I dress the way I want to within the parameters of my professional role.