How do I feel better about my looks?

September 6, 2014 4:59 PM

Being the adult human being that I am, I'm not as thin as I was in my early 20s. Intellectually, I am fine with this. Emotionally, not so much? How can I be more confident about the way I look?

It's not that I don't want to lose weight, it's that, to be honest, losing the 10-20 pounds I could stand to lose is not going to make me look like my mental image of myself, circa high school/college. And I don't think it's particularly healthy to obsess about wearing a size two as opposed to a ten, which is a perfectly fine size for a grown ass woman to wear. But, I don't know, I guess I'm willing to hear "drop ten pounds" if that's the consensus.

Mostly, I'm just unhappy with the fact that, every time I see a full body photo of myself or catch myself in a mirror, I... don't look like what my mental image of my body has been for my entire life thus far. I was a scrawny kid, a skinny teenager, a slim twenty-something, and now... well, I won't call myself fat, but I'm no longer thin, either.

I'm sure I'm not dressing for my "new shape". There might also be an element of dressing my age at play. I don't like fussy clothes and have never had a particularly feminine aesthetic. It strikes me that when I (an early-30s woman) wear a baggy t-shirt and cutoffs with sneakers and no socks, I no longer look like a badass DNGAF tomboy. I look like a bag lady. Being short and pear shaped in a fashion moment when the current shape is baggy on top and tight on the bottom, with a side order of booty shorts and ankle straps, doesn't help.

How do I own this? Do I just keep being me, and if people think I look like a hot mess, so be it? (My work clothes are appropriate and I seem to be doing OK in terms of like what to wear to a nice dinner or a wedding or the like.) Should I radically alter some aspect of my life, and if so, what should that be? Is this an emotional problem to move past, or a physical problem to alter with better clothes and maybe some weight loss? Inspiration photos of a tomboy aesthetic as modeled by someone who isn't rail-thin Charlotte Gainsbourg, Diane Keaton, or Patti Smith would also be lovely.

posted by Sara C. to Clothing, Beauty, & Fashion (31 answers total)

Best answer: Is this an emotional problem to move past, or a physical problem to alter with better clothes and maybe some weight loss?

I don't think these are mutually exclusive ideas.

IMO your primary focus should be on your emotional and mental well-being (since your weight seems well within the healthy range). But, you may find it easier to come to terms with your new look - and therefore to maintain your emotional and mental health - if you can address the physical side of things, particularly through better clothing. There is, in my view, a real mood boost that comes through feeling confident in your appearance, and that can be easier to attain than simply willing yourself to feel good about yourself.

So, while I'm certainly not going to suggest you fret over a new diet and exercise regimen, you could probably benefit a lot from a new wardrobe. Unfortunately while I'm also short and slightly pear-shaped, my personal aesthetic is pretty feminine, so I'm not sure how helpful I can be with specific clothing recommendations. I will say that structured pieces, especially up top, can go a really long way in balancing things out and creating an overall slim look.
posted by schroedingersgirl at 5:25 PM on September 6, 2014 [2 favorites]

Best answer: You work at it like you work at everything else! I'm fat, and I love myself, looks included. It didn't just happen overnight. I had to work at accepting myself and then loving myself. Buying clothes you like helps, as does other self-care stuff like cosmetics (for me it's perfume and lip balm but lots of my fat friends are way into makeup), shoes, food you like, etc. I know I look this way for lots of reasons; I'm into butter, I come from round people, I'm clumsy, and I hate being hot/sweaty. I'm okay with all of those things! It's hard to separate fat stigma (you are not fat but this stuff is super ingrained into our culture) like if you're not skinny then you're lazy, or if you're not skinny you're automatically unattractive, from your self-image but once you do you'll be way better off! Get used to how you look, then get INTO it. If exercise makes you feel good, do that. If it makes you feel like shit, don't. But your body will always change, and being able to embrace it all the ways it looks is a great feeling.
posted by masquesoporfavor at 5:35 PM on September 6, 2014 [6 favorites]

Best answer: So, while I'm certainly not going to suggest you fret over a new diet and exercise regimen, you could probably benefit a lot from a new wardrobe.

For what it's worth, this is pretty generally true. People end to dress for a previous period in their lives, rather than for their current physical and social lives. Bodies change, so even if you were your high school weight the clothes you wore then probably wouldn't work, and even more our social worlds change.

And, these things aren't exclusive. You can dress flatteringly today, and if tomorrow you want to start a new diet and exercise makeover then that's ok too. Don't let the one be a barrier to thinking about the other.
posted by Dip Flash at 5:37 PM on September 6, 2014 [3 favorites]

It's not that I don't want to lose weight, it's that, to be honest, losing the 10-20 pounds I could stand to lose is not going to make me look like my mental image of myself, circa high school/college.

Why not? The rest of your question then goes on to talk about your weight and nothing else.

Just trying to unpack your issue here.
posted by unannihilated at 5:38 PM on September 6, 2014 [2 favorites]

Best answer: Buying appropriate clothes makes a HUGE difference. I'm 29. I've had two kids. This time last year, I had a one month old baby and 30 more pounds than I do now, on top of all sorts of postpartum body changes. I felt like crap. I did NOT want to buy new clothes. But, I did, and it was fantastic. Suddenly my body felt more acceptable. I don't have advice for your particular shape (I'm tall and pear-shaped, and dresses/skirts are definitely my thing), but I do recommend spending the time and money to create a wardrobe that makes you feel good when you wear it, EVEN IF you're going to lose weight.
posted by linettasky at 5:59 PM on September 6, 2014 [7 favorites]

Best answer: Ooh just thought of--you could sign up for Gwynnie Bee. I think they start at size 10 and are like the Netflix for clothes. I kind of hate their customer service and I think they charge a bit too much BUT having new things to wear constantly means I get a lot of compliments which feels great, and just..having new things is fun (and the first month is free so it's worth a shot). I think StitchFix or something would also work for you. I use GB since they're the only plus size option, so I'm not familiar with the others.
posted by masquesoporfavor at 6:04 PM on September 6, 2014

Best answer: I can definitely relate. In my 20s (1980s), I lost 80 pounds and worked out. My self-concept changed. But 9 years ago, I gained 3 sizes in 8 weeks; we don't know why (I see an endo). I still think of myself as the swimmer and ice-skater I used to be and am shocked sometimes by the mirror.

Should I radically alter some aspect of my life, and if so, what should that be?

I would urge you, if possible, to take up yoga and some form of weightlifting. I suggest this not for any potential physical benefits, but for the mental and emotional benefits!

(My work clothes are appropriate and I seem to be doing OK in terms of like what to wear to a nice dinner or a wedding or the like.)

Well, that is great!
posted by jgirl at 6:09 PM on September 6, 2014 [4 favorites]

I got over my extra 20 pounds after 40 body issues when my best friend, who I love dearly and who I think is beautiful, told me her weight and size. She and I are close in size. I would never think ugly things about her so I decided to stop thinking mean things about myself. I have also decided that everyone who eats and poops has a stomach that pokes out. It is natural and normal and I'm just not going to stress over it any more. Wear what you are going to wear and be comfortable. You are not trained or paid to fly a jet engine so you do not drive a jet engine. You are also not paid or trained to be a super model or an actress. So don't try and look like one.
posted by myselfasme at 6:21 PM on September 6, 2014

Best answer: I agree that new clothes help a lot. I am in a similar position; trying to figure out what to wear that is flattering at my current size and age is very different than when I was younger and trim and could wear whatever and still look good. And I, too, have generally had a style that's not terribly feminine, and I feel like more girly-type clothes are now more flattering, and reconciling that with my taste is tricky.

I'm still working on it myself, but in my case I'm finding that shirts with princess seams work well with either jeans or dress pants and fitted blazer-type jackets help me look and feel more put together. I'm also embracing dresses; I go for those that are fairly plain (never fussy/ frilly) but that have some ease or ruching in the stomach area to make my belly less obvious. (And I can wear them with boots and feel like a 90s riot grrl or something.)
posted by metasarah at 6:23 PM on September 6, 2014 [3 favorites]

Response by poster: Why not? The rest of your question then goes on to talk about your weight and nothing else.

Partially because, when I was 18, I weighed 95 pounds, and that's not a realistic goal weight for me at 33.

And partially because, frankly, when I was a 95 pound eighteen year old, I hated the same parts of my body that alarm me today. Losing ten pounds is not going to give me longer legs, skinnier upper arms, or magically make me not carry most of my weight in my butt/thighs. I am never going to have that long, lean body type that inspires me to pin a fashion editorial photo to my "Fall Style" pinterest board, no matter how few carbs I eat.

My mom has exhibited signs of disordered eating and body dysmorphia ever since I can remember. I don't have the hottest track record on that stuff either, and up till now my solution has been to work very hard at not caring about my appearance. Which is something that is not really an option as one heads into middle age.

(Not that I am middle aged, but I'm going to be, someday, and I'd rather tackle it gracefully.)
posted by Sara C. at 6:28 PM on September 6, 2014 [11 favorites]

Best answer: I just want to say, "welcome to the club!" I have to stop myself from buying clothes that would have flattered the 20something me that do NOT suit the body I have now. Part of my problem was that I went through several years of being a broke student and not being able to afford lots of new clothes, and then when I finally could afford them, I'd undergone cancer treatment and instant menopause and my body had changed shape (yay menopause!). It took me quite a while to get used to the body I have now as opposed to the one I had the last time I could splash out on clothes.

I have found the website/blog You Look Fab to be a tremendous help in dressing for my current shape. They address a lot of the issues around dressing for the body you have, and their bloggers/posters are of all ages, sizes, and shapes.
posted by Rosie M. Banks at 6:41 PM on September 6, 2014 [2 favorites]

People have covered all the bases above so I'm just going to offer three suggestions:

a) A blog called tomboy/femme style. I love it and perhaps you'll find some inspiration, too?

b) Whenever you see someone with an outfit/haircut/accessory you love and a similar body shape to yours, ask them where they got it -- and then go check out the store/website/whatever yourself! (After all, nearly everyone loves genuine compliments.) This is the way I found my current local hairstylist and also the way I've found some great clothes from nearby. There may not be many people with your look or style around but, when you do, the potential lead will be worth the ask!

c) a pair of wonderfully tailored-to-fit trousers. Even if you can't afford a pair made just for you, you can probably afford one altered to fit perfectly and look amazing. (White socks optional)
posted by smorgasbord at 6:59 PM on September 6, 2014 [3 favorites]

Best answer: To me, it sounds like you need to work on your casual style and change it up a little. When you have a purpose for what you wear, like work or a wedding, you say you do fine, but when you're just hanging around, you feel like you don't look good. So maybe updating your casual choices might help, since you'll feel good if you think you look good.

I find that trying on clothes that I would normally never buy helps me solidify what I actually do want to see myself in. So if you're having trouble determining a style or picking something other than what you usually would, try on some stuff that is OK but outside of your comfort zone. Maybe a different fit of tshirt or unusual color, cargo skirt vs shorts, different jeans fit, etc. You'll either discover something that works that you didn't expect, or you'll discover the exact reason why you don't like that specific thing, which will drive what you do like.

In terms of your body, the thing that helped me was appreciating what I can do more than what I look like. For me this meant exercising and challenging myself with new activities that are intimidating but doable challenges. I remind myself that my body got me this far and it's just following orders that the DNA gave it, so it doesn't deserve any badmouthing, just like a puppy that doesn't know any better than to chew.
posted by blnkfrnk at 7:03 PM on September 6, 2014 [3 favorites]

I was never a skinny kid, but I am slowly and steadily getting bigger over the years. I do catch myself in a mirror or store window and see my slouchy shoulders and pokey tummy and go "Ugh, yuck." But then I just try to convince myself to drop it. I remind myself that I'm not willing to make myself uncomfortable in order to stop this from happening, and I try not to buy stuff that actively makes me look worse, so what else can I do? You can either fix the problem or decide to be okay with the problem. If this sounds flippant, it's truly not. I have this conversation with myself several times a day.
posted by bleep at 7:06 PM on September 6, 2014

What helped me a lot with this sort of thing is to realize that a body is a project.

Could you look like an Olympic swimmer if you wanted to?
Yes, if you were swimming 6 or so hours a day.

How important is this to you?
How many hours can you dedicate?

You have two options here. You can choose to accept this body, or your can choose to change it.

If you choose to accept it as it is and its future state, you don't have to make any big changes, and most importantly, you are not allowed to be upset about something that you can change but have purposefully chosen not to change and have chosen to love.

If you choose to change your body, welcome to the beginning of middle age, this will be work.
I don't know what kind of eating and exercising you do right now, but if you want to lose 10-20 pounds and you are already so small it will take you a long time to get there. (Maybe 4 months to a year, 5-6 hours a week?) When your goal is to lose weight or change your body, this project must come before almost all other projects. You will have work, you will have the gym and your food, and everything else comes after those two things.

If you give your all to the project of losing weight, you will succeed. If you do not give it your all, you will not see changes, and if you recognize you are not giving the project the work it needs, you cannot beat yourself up over the condition of your body.

Your body is just doing what your body does.
If you want it to change, you have to make it change.
If you do not actively, daily, purposefully change, it will not change.

If you choose not to change, please learn to accept yourself and love what you have. I am certain it is a body that many, many women would love to have.
posted by littlewater at 7:06 PM on September 6, 2014 [12 favorites]

who gives a fuck what the current fashion is? i mean really. it is just going to change in a year and if it doesn't work for your body type, even if you were WEARING the current fasion you would look bad/stupid/weird.

if you want to wear cargo pants and a tank top (that fit well) then do it. you should be wearing clean and kempt clothes. they should fit right. you will feel better about yourself in that than dirty torn too big cargo pants and tank tops.
posted by misanthropicsarah at 7:09 PM on September 6, 2014 [1 favorite]

I found these sites very helpful. An expression of Dress to Express was something I was looking for.

http://www.alreadypretty.com/
http://geekthreads.blogspot.com/2010/01/adding-pizazz-to-corporate-wear.html
posted by jellyjam at 7:39 PM on September 6, 2014 [1 favorite]

You get proud by practicing.
posted by Soliloquy at 7:40 PM on September 6, 2014 [1 favorite]

I was pretty skinny up until my mid 20s, when I hit the trifecta of slowing metabolism, getting a desk job, and having enormous kosher lunches paid for by my employer every day. I don't remember what I weighed when I was skinny, but by my late 30s I was 50-60 pounds heaver than I'd like to be. Last year I managed to lose about 35 pounds.

It's not that I don't want to lose weight, it's that, to be honest, losing the 10-20 pounds I could stand to lose is not going to make me look like my mental image of myself, circa high school/college.

Well, maybe not exactly... but for me it was pretty cool to look in the mirror and see someone who looked more like college era me than I'd seen in a long time... and it was enough of a change that it pretty much forced me to go buy new clothes, and for the first time since the late 1990s I bought clothes that actually fit instead of the default "err on the side of too large" stuff I'd been wearing. It was a big confidence booster and sense of accomplishment.

Then the holidays hit and I got lazy about nutrition and have put 5-10 pounds of it back on this year... but still, even though I'm fairly comfortable with the fact that my 20 year old self is long gone, it was pretty cool to rediscover that skinny me is still in there somewhere, grey hairs or no.

On review, everything that littlewater said.
posted by usonian at 7:45 PM on September 6, 2014 [1 favorite]

Best answer: How you feel about your body and what you wear are obviously closely intertwined, but are also things that can be tackled separately. Finding more peace with your body as it is can help you feel more comfortable with your clothing, and finding clothing you feel good in can make you feel better about your body.

I'm really not an fit/athletic/exercise-loving type, but I find small actions that focus more on "health" than "weight" are helpful to my perception of myself. Healthy meals, going for a walk, doing yoga, these are things that are good for my body and make me feel good about my body.

As far as clothing goes, yes, a tight on the bottom/loose on top look is in right now, but so is the opposite! Boyfriend jeans and joggers are two examples of non-fitted bottoms that are very common and tomboy friendly. If you've written off tight bottoms and haven't tried any on for a while, you might want to try again. Skinny jeans are sooooo stretchy these days. I have a couple pairs that are actually very comfy.

It's also easy to put a tomboy spin on more feminine or figure flattering looks. I love high-waisted circle skirts - they're everywhere right now and in every length. They can be super comfy - no restriction or fussiness other that a stretchy waistband. They hide my butt and make my short little legs look super long! With a favorite band tee or a fitted breton top and some converse they don't have to look super feminine.

As far as inspiration, here are a couple blogs I follow that don't feature the typical "fashion" body type:
- Lost in a Spotless Mind (Here's a post she wrote about body image that may be interesting to you, and here is an example of a high-waisted skirt)
- Girl With Curves (rocking some skinny jeans and a simple tee, wearing some cute joggers)
- Wardrobe Oxygen (in boyfriend jeans, and a circle skirt paired with a plaid flannel buttondown)
- Nadia Aboulhosn (more boyfriend jeans!)
posted by brittanyq at 7:51 PM on September 6, 2014 [5 favorites]

Best answer: Welcome to the "all my weight is on my hips" club!! I'm a small person, but I have a large hip/butt ratio. People are surprised to hear the size pants I wear. So, even though I'm small, I've recently gained some weight and gone up a pants size or two. I'm fine with this. My weight is healthy, but I totally know what you mean by not feeling like it's the body you're used to.

Maybe this rings true for you, but holding up pants and underwear that I know are my size I think "Wow! Those are huge!" then I try them on and sometimes have to go up a size.

1) Don't worry about size or numbers. Just get what fits.

2) Learn the love and accentuate certain parts of your body. Yeah, maybe all your weight's in your butt, but maybe that means your butt looks AWESOME in pants!

3) Abso-freakin-lutely get some clothes that fit and flatter your shape. Personally, as a hip-heavy person, I LOVE Express's pants.

Also, mildly upgrade your laze-around stuff. Maybe a more flattering t-shirt cuts and jeans that fit great. And yeah, I'd stay away from too-big on top and small on bottom looks. Leggings and a big top don't work for ladies like us. I'd go with a nice blouse/cardigan and some good fitting pants/jeans.

4) Try on stuff! If you're fitting a new shape then stuff might fit and look great that you never thought would! I even just got some blouses that look horrible on the hanger but really flatter my body! Then you can learn what stuff works and what stuff doesn't.

Honestly I just did TONS of clothes shopping as my work just upgraded their dress code. So seriously memail me and I can let you know more what works for my shape.

Edit: How's your shoe game? I know awesome shoes can boost your spirit as you shoe size usually stays the same! And don't forget about well-fitting undergarments - new undies and bras (that fit! Try reddit.com/r/ABraThatFits)
posted by Crystalinne at 8:58 PM on September 6, 2014 [3 favorites]

Best answer: You're right that the weight isn't the issue. Even without gaining weight or having kids, my body changed significantly in my late 20s (boobs! hips!) and there was a lag while I figured out how to dress it. Keep being you, start culling things that you think make you look like a hot mess and adding stuff you think looks good.

Being well-groomed otherwise (haircut, brows, makeup if you do that) makes it easier to pull off DGAF clothes as an adult. I'm also starting to try more classic prep style - comfortable, timeless clothes that read "yacht club" more than "bag lady". Muffy Aldrich wears mostly tomboyish/unisex preppy clothes.

2nding weightlifting and/or yoga to help you appreciate your body and with a possible side bonus of muscle definition.
posted by momus_window at 9:03 PM on September 6, 2014 [3 favorites]

And second post (can you tell I've had body issues?)

I love the Nu Project (Warning NSFW Nudity Ahead)

It's real photos of real women, naked. Tons of different bodies and shapes. It really made me realise that everyone doesn't look like a barbie.
posted by Crystalinne at 9:04 PM on September 6, 2014 [3 favorites]

I know the look of which you speak and get why you love it. For me, a lot of the appeal of that look is tied up in the idea of being young and not-giving-a-fuck, being wild, eternally strong, effortlessly beautiful, and free. I've never been tall enough or skinny enough to pull that off. But, I am also not really the romantic ideal that is represented in those pictures. I'm not so wild; I follow rules and get scared sometimes when people break them. I'm shy around people I like. I look like crap when I don't take care of my appearance. I do give a fuck, about a lot of things that are honestly kind of silly and uncool. And, now that I'm in my thirties, I'm not sure I'm really young anymore. At least, not in the way that those models look in the photos.

Part of the process of accepting my body has been coming to accept myself for not being the person in the photos. I think it might help you to think about what you value about yourself and how the body you have supports the person you are.

For example: I play hockey and run a lot; my body is short and stocky but also pretty strong and good at putting on muscle. If I had a skinny tomboy body I probably wouldn't enjoy those things so much. I also write code for a living, and my rule-following approach is what helps me pay the bills. Sure, I could probably do those things with that fantasy body, but then I wouldn't be me. I wouldn't have made the friends I have, nor challenged myself in the specific ways that shaped who I am today.

I think you can probably find similar cause and effect in your own life. If you are happy with where you are in life, remember that you couldn't have gotten here without having the body you have.

After writing all this it sounds like I'm saying that it's purely an emotional problem. However, I found that it was a lot easier to accept me as I was when I made the effort to dress myself for the person I am today. Just eliminating the feeling that I wasn't looking as good as I possibly could has helped a lot. It's easier to be proud of something that takes time and effort than it is to like something you can't change.
posted by rhythm and booze at 9:18 PM on September 6, 2014 [10 favorites]

Best answer: I'm going to enthusiastically pile on with the suggestion to exercise. A side effect is that it will help you lose weight. But I spent most of my life loafing around and feeling like a brain in a lumpy sack, and then I discovered how awesome it was to sweat and use this body. I bike and run and climb stairs and carry heavy things around all day long and it's just so great to feel confident about my strength instead of uncomfortable in some shape I have no control over.
posted by jeweled accumulation at 11:10 PM on September 6, 2014 [9 favorites]

Best answer: That transition from "I'm not the kind of girl who worries about her weight" to "oh, this is what everyone meant when they say after 30 is a whole new body" has taken a while to sink in (I'm a few years older than you) but your mental image does eventually catch up with the mirror image. Mostly. The pot belly changed shape, the body fat got mushier, and I went up a surprising number of bra sizes (cup and band). I was baffled to find that I couldn't fit into a favorite pair of knee high boots. I learned that elastic waistbands are a glorious thing and that having a house dress to change in to when I get home is a sheer delight (bye bye bra!). The baby doll dresses and size small hipster tees of the past have gone to Goodwill.

So that's Suggestion #1 - pick comfortable home clothes, maybe even rather revealing tank tops and short shorts, but comfortable - and try a 10 minute yoga video off of Youtube or put on a homemade face mask and from time to time eye yourself in the mirror. "Hi me! Looking comfy!"

Suggestion #2. If you find kids generally pleasant to be around, watch how they inhabit their bodies. I hang out with some toddlers and I love how the little girls just parade around with their bellies out. I haven't stopped habitually sucking in my stomach but when I hang out with my friends' kids, I experiment with letting my belly just balloon out, sometimes even inflating it past its wont. Or even younger kids, the ones who just figured out that feet are definitely different from hands. Watch them learn how bodies move and remember how your own body is still muscle and sinew and synapses.

Suggestion #3. I think you are in L.A. so have easy access to Korean sauna/spas. Bring a pal who is game, or if not, go solo, and hang out naked for a few hours. Look at the grandmas' backs. The middle aged butts. The young guns. Try not to be caught staring, but look at people enjoying themselves and their variously-shaped bodies. If you can splash out a bit, get a scrub massage and marvel at how much dead skin just rolls off your body. Be a little grossed out. And then feel awesome and soft and shiny for the rest of the day.

And yeah, nth-ing everyone who says build strength and renew your wardrobe, but honestly that is a slow process (though omg, who knew jeggings were actually amazing. I thought I never get down with skinny jeans because NOT COMFY but jeggings are my new plane pants). Lounging in a muumuu, having a big belly contest with a 4-year old, and getting an inter-generational eyeful is my go-to "body image reset button".
posted by spamandkimchi at 1:23 AM on September 7, 2014 [6 favorites]

I totally sympathize with you. In my head I still should look like my teenage self, and I hate that so much that is in style these days is so damn tight around the hips. However! there is another amazing trend going on that is super flattering and easy to wear! fit and flare dresses. all you need to do is find a colour and pattern you like, check that the waist is the right size for you, and you'll look great. I know that this maybe doesn't seem like the most enlightened way to come to body acceptance, but having some fashionable items that you know you look great in and feel comfortable in can go a long way to making you feel better. Works for me, anyway.
posted by 5_13_23_42_69_666 at 4:51 AM on September 7, 2014 [1 favorite]

Response by poster: Oh man dammit I didn't want to do Stitch Fix, but now I might really do Stitch Fix...

Also, the recommendations to exercise more for health and just to be comfortable in my body, coupled with some recent the-fun-kind-of-sore physical activity experiences, are inspiring me to figure out what a functional/realistic fitness regime would look like for me.
posted by Sara C. at 8:48 AM on September 7, 2014 [2 favorites]

Chiming in to agree with what everyone has said here. What's helped me the most is casual uniform dressing, which is to pick an outfit that you know is flattering and to buy lots of variations in different colofors. I feel the worst when I am at the bottom of my laundry and stuck wearing that weird, ill - fitting skirt from high school (or whatever). My uniform is pretty casual, cribbed from some blog post I can't find now, leggings, knit skirt, tank top, interesting tee on top. But it's flattering and works for me and takes out the stress and pain of getting dressed and hating my body blah blah blah.

And I know what you mean about a history of body unhappiness. My facebook timeline is like a monument to all the times I thought I was fat, but want. I almost didn't let myself have kids because I was so scared of bodily changes. Now I'm fatter than ever, with stretchmarks, to boot. But my hair is long and shiny, my boobs are big and nurturing, my arms strong from carrying my baby. I finally love myself. Sometimes you have to give up striving to be happy. I'm glad I did.
posted by PhoBWanKenobi at 12:21 PM on September 7, 2014 [2 favorites]

YMMV but for me, some of it was yes, recognizing I still carried a conception/self image of myself (unchanging since, like, age 13) as a straight-up-and-down, not-fully-grown imp-type, the sort in fashion pictures who can wear tweedy or whimsical/unique or boyish certain-sort-of-genderqueer lovely Peter Pan youth clothing easily like it was meant for them, and yes that was awesome, but no amount of dieting or exercise or whatever would ever get me back to that pubescent aesthetic...and that what I look like now is conducive to cuts of clothes I never would've felt right in back then, and adjusting for that because yes, there are notions of identity wrapped up in those clothes, this idea you get to choose from everything and it "says" something about you and your demeanor and interests, when, the older I got, the more I felt like it's not that simple. I dress femmer now, not because I FEEL any more femme (sure as hell don't), but those are the clothes that fit and feel good on my frame (again, YMMV, these are just my own specifics as my adulthood figure change involved growing a larger chest than pre-25-not-even-an-A-cup-me ever imagined I'd have). I guess what I'm trying to get at is that it is sort of a mix of examining the psychological stuff with the straight up dressing yourself and feeling physically good in yourself thing. Body shapes and the clothes that are made for them have these culturally coded, loaded meanings, and unpacking how you feel about that--and deciding after acknowledging your feelings there how to go about things, whether it means shopping harder because you say fuck it to all that, which is cool! or something more of a lazy compromise because you've thought it through and are ok with that, or whatever else--can be a good first step. It was for me, at least.

I think a pretty big thing wrapped in all that headfuckery is that successfully shopping for clothes becomes a much more deliberate, thought out task when you get larger or curvier. That's been my experience anyway--I used to be able to stroll in to anywhere, whether it was Goodwill or some cheapo teenybopper mall boutique or UO or whatever, and just assume I could probably wear anything I saw on a rack (like they'd have it in my size, and it wouldn't be unflattering either), and it'd be so easy and cheap. Having that most absolutely stop being the case was rough, and really fucked with my head. It was worth taking some real time out and tackling where to shop, places full of stuff that WOULD look good on me, with my size carried, to stop trying and trying to shop like before and feeling like a freakish invisible-to-clothesmakers pariah. Taking the time/effort to do some research to find spots that had clothes that made me look great reminded me I'm NOT gross now, I CAN look wonderful, my figure is just as worthy of admiration as before, which was for me important.
posted by ifjuly at 12:56 PM on September 7, 2014 [3 favorites]

I am in the exact same boat. Things I have done:

1) Started a Whole30, because I know some of the weight I've been gaining is due to unhealthy lifestyle.

2) Started running and doing strength exercises (Ballet Beautiful DVDs), because a fit fat body feels more awesome than a thin unhealthy body.

3) Buying clothes in different shapes that look good and/or make me feel comfortable. I wear empire-waist dresses when I want to feel young and beautiful and carefree (never wore these before), and they are loose around the tum and hips and comfortable. I have a pair of harem pants. Idgaf. I am experimenting more with new cuts and shapes because it's much harder to dress my body now than it was at size 6. Everything I know is now wrong! I still haven't figured out jeans, but I've bought more new skirts that I love and I'll keep looking.
posted by stoneandstar at 5:24 PM on September 7, 2014