comfort uber alles
March 9, 2020 6:08 PM   Subscribe

Although I make cursory efforts to coordinate my clothing, I don't really wear nice outfits because they don't seem very comfortable. Some days, I think, wouldn't it be neat if I paid more attention to my clothing? If you were ever similar to me but then became somebody who dressed nicely... how did you change this?

Back when I was in a work environment in which there was a clearer and fancier dress code, I went out and bought some clothing and put together some outfits that weren't that bad. After I left that workplace, I found myself back in good old sneakers, flats, Birkenstocks, and snow/hiking boots because that was/is all within the realm of acceptable at my current job.

I do have some nice dresses and shoes, but I don't wear them because I always default to the most comfortable thing I have. I have a few pieces of jewelry, but I also don't wear them because it's not comfortable to have jewelry on (I think I'm a slightly allergic to the metals). I haven't purchased a new watch for the past 15 years because I somehow keep thinking that it'll be fine to keep using my phone to tell time.

I think there are multiple mental obstacles keeping me from dressing more nicely. I think that part of it is just that I don't really like spending money on stuff that doesn't seem necessary. I don't like having a lot of stuff. I don't like buying things that I don't use, and I feel like experimenting with fashion could end up being pretty expensive with little result (maybe part of me feels resigned to the comfort of jeans and t-shirts?). I can recognize that things like jewelry and nice shoes can tie outfits together, but I am also up against this mindset of wanting to find a completely, perfectly versatile accessory such that it pretty much paralyzes me from ever buying anything. Sometimes I don't want to buy something because I'm afraid it is too large a departure from whatever my previously defined style was. Or maybe I feel like I can't pull it off. So... I'll go shopping and end up with more solid-colored t-shirts that I found on clearance. Or I'll go to Uniqlo and find the most comfortable, shapeless dress there.

I also think that part of it is that my workplace is kind of shabby - the office building is run down. Sometimes my work involves crawling or sitting down on the floor or grass. My other work site is an emergency room... and on top of that, I'm always schlepping between cities on a Megabus or Amtrak, and part of me just feels like, why would I bring my nice coat and shoes into a dirt/germ fest?

I have one bag, one coat, and 2 pairs of shoes that I wear to work, even though I probably own about 8 pairs of shoes and 3 bags total. I have a pair of heels that I have never worn outside the house. I stopped wearing my nice wool peacoat. I have a nice pair of boots that I just don't wear because they're still slightly less comfortable than sneakers.

Is this even a problem? Most of the time I think that if I never had to consider what I was wearing ever again, I wouldn't really miss it, even though I can also appreciate a stylish outfit and admire fashion designs, and sometimes I do feel like it would be nice to wear cool clothes while I'm still young and can try a variety of styles before being relegated to Eileen Fisher et al. ...

Would appreciate any perspective on how I might be able to reframe fashion/dress so that I can make it more palatable and achievable. I'm a 20s F.
posted by gemutlichkeit to Clothing, Beauty, & Fashion (17 answers total) 23 users marked this as a favorite
I read a book recently that’s called The Curated Closet that is really amazing. It’s got a step-by-step process of defining what you want your style to be, what your life actually looks like, and even a laundry formula! I think if you don’t want to spend money on stuff that doesn’t feel like “you”, it’s a great way to figure out what you want “you” to look like.
posted by itsamermaid at 6:27 PM on March 9, 2020 [9 favorites]

I switched from wearing jeans and t-shirts at work to wearing mainly dresses a few years ago. Like you, I tend to go for whatever the most comfortable thing is in my wardrobe, so I had to let it get to the point where the only jeans I have are not really acceptable for wearing outside the home (stained, faded, holes, etc). Then I don't have the jeans option.

I also made sure I only bought super comfortable dresses. There are plenty of options that are not shapeless but are very comfy (more than jeans, actually!) Now I've been doing it for a while, I find dresses way more comfortable - no restraints around the thighs or waist, nothing rides up or down, etc.

One secret is I buy a lot of my dresses from places like hiking stores (or second hand shops, but getting the same brands), where you can get things made of soft, breathable material, which you can move very freely in. Like, take a look at these. Many would be work-appropriate for a place where you can wear jeans to work (or even for more formal workplaces). I also buy clothes from eShakti, which makes them to your own measurements. A properly fitted dress is VERY comfortable (and most of theirs have pockets)!
posted by lollusc at 6:36 PM on March 9, 2020 [8 favorites]

I also came here to recommend The Curated Closet! I'm currently working my way through it and the associated workbook. Warning: it is a fair bit of work.

But the nice thing about the book is it completely meets you where you are. Many such books assume things about your lifestyle and prescribe particular clothes for you - but not everyone needs a white button-down shirt. The book really has you think through the kinds of clothes you'll actually wear and figure out wardrobe holes that make sense for your lifestyle.
posted by peacheater at 6:50 PM on March 9, 2020 [3 favorites]

Two things stand out to me in your question: one is your ambivalence. You ask if this is even a problem. It's only as much of a problem as you think/feel it is. Capitalism and gender norms contribute to the size of the problem. I don't know you or your values; you can decide how much that matters to you.

The other thing that stands out to me is that you choose shapeless dresses and don't use clothes as a way to define yourself. It's ok. Some people are less appearance focused, you may be one of them. If you want to learn about dressing in ways that flatter your body, I'm sure people will offer lots of practical advice about that. Do you feel ok about your body? Do you want to be looked at? You seem uncertain.

It's fine to just be less appearance-conscious, but if this is a body shame or low self-esteem thing, you might be able to experience more joy from your body and physical expression than you currently do if you work on it in therapy. Only you know that.

FWIW I am kind of lazy about clothes and don't like to spend a lot of money on them. One thing that really bothers me is if I buy something and its impractical or never gets worn. I don't like to waste money. I have kind of a formula/uniform where I buy a few bottoms and tops in a silhouette that flatters my body, in a very limited color scheme with neutrals on the bottom. Everything matches with everything else. Many people use variations on capsule wardrobe strategies to deal with the overwhelm of putting outfits together and to avoid waste, while still looking "put together."
posted by unstrungharp at 7:01 PM on March 9, 2020 [8 favorites]

Came to say exactly what lollusc said--I own only jeans and dresses (plus a pair of black slacks for Work Events). And I had not owned a dress in 20 years before a few years ago.

The key for me was to be able to do anything--so the shoes still have to be good for running to catch a bus or whatever, and for standing/walking for hours at a time (even if I'm not planning that). But my job involves bending, crouching, reaching, and sometimes lifting boxes, so I had to be able to do all those things. I wear a lot of fit-and-flare dresses in knits (so there's stretch) and they are just as comfortable as jeans. I wear sneakers or Mary Janes (sourcing comfortable shoes is harder than clothes for me) with them.

I also got one pair of small silver hoop earrings that lock (meaning a continuous ring) and just wear them literally all the time. For a wedding, I might change my earrings. But I think it adds a purposeful look, and I don't know they're there.

I basically loved my coworker's clothes, figured I'd try one dress from where she shopped, and it was the most flattering and comfortable thing I'd ever owned, so I was hooked.

I get a lot of my dresses at Eshakti, which some people find hit or miss but which I love, especially because they make them to your size, and my sizing is weird. This one just arrived this week. I have learned that I can only get things in knits, and that I don't like the lowest of their neckline options, and that I'm most comfortable with things that fall below the knee. (Anyone who wants $10 off their first order MeMail me!)
posted by gideonfrog at 7:02 PM on March 9, 2020 [1 favorite]

My work clothes are stretchy dresses and flat, comfortable boots in winter, stretchy dresses and flat, comfortable sandals in summer, pretty much no accessories of any kind. If I’m only wearing one outer garment, it doesn’t have to match anything else. I’m not sure how successful this is, but I think I’m passing as professional-looking business-casual, although a little unadorned, and everything is absolutely comfortable.
posted by LizardBreath at 7:15 PM on March 9, 2020 [1 favorite]

here's an easy and comfortable way to style-up any outfit; a silk scarf. You can drape them in all kinds of ways, they're soft and comfortable around the neck, take up almost no room in a closet, go with almost anything, and most thrift stores will have a box of them for a buck or so each. Get a few in colours that bring you joy, and enjoy your newfound panache.
posted by 5_13_23_42_69_666 at 8:47 PM on March 9, 2020 [4 favorites]

First - my interest in clothes is a fairly solid indicator of my mental well-being. If I'm depressed, I stop caring about clothes and I revert to the most boring things I own. When the depression lifts, I get excited about mixing prints and playing with jewelry. So if in general you're having trouble finding joy and excitement in life, that might be worth thinking about. That said ...

My "nice" clothes need to be comfortable or I won't wear them. My nice shoes are Aerosoles, Naturalizers and Earth with low heels. And I also have some flat oxfords that just make me really happy to wear.

It sounds like one way to gently "level up," might be to buy comfortable clothes in washable, flattering colors and prints. Striped tees and button-fronts can be really comfortable and not too expensive. I picked up a $5 jacket at Goodwill that's comfortable and can also change a really boring, frumpy outfit into something that looks intentional and trendy.

As far as cash - if you're okay with thrifting, that can be a way to experiment a bit more freely with less worry. It really helps me to take a friend when I shop, and also to give myself permission to return things ruthlessly.
posted by bunderful at 9:18 PM on March 9, 2020 [1 favorite]

Depending on your body shape and how you feel about gender presentation, skewing more masculine can get you a bunch of options for smart and still comfortable. They can be made into a "uniform" so you don't have to make decisions every day, and are normally worn without a ton of accessories beyond a belt that goes with the shoes.
posted by quacks like a duck at 12:04 AM on March 10, 2020 [3 favorites]

My work uniform is button down shirts and skorts (worn with thick knit tights in the winter) from Eddie Bauer. They don't wrinkle, they don't need to be ironed or washed in a fussy way, they repel liquids, they stretch and they all have pockets. I have three skorts, three shirts, and a couple other dresses from Eddie Bauer that are made of the same stuff (a shirtdress and wrap dress). I don't care about clothes and wish we could all wear, like, Star trek jumpsuits instead, but I do have to look reasonably nice for work and these are the most comfortable most I don't have to actually think about them garments I've ever owned.
posted by soren_lorensen at 1:19 AM on March 10, 2020

Comfortable + more dressy/formal clothes exist, but they cost more money. It can take time and effort, too, to try on lots of different things to eventually find the brands and fabrics and styles/fit that are comfortable for you (eg. depending on body shape and personal style). But if you don't have to wear dressier clothing for work, and if "shopping" in the sense of regularly poking your head into different stores and trying things on isn't for you, and if spending more per item on clothing is not something you want to do or feel comfortable with, then there is no reason to change up your current wardrobe!

There are a few items that can make a low key wardrobe come across as dressier with minimal effort, that you could focus more limited time and money on.

Nice but comfortable shoes: find a yuppy shoe store that lots of folks in yoga casual clothing seem to frequent, might market itself (in North America, I'm assuming) as having European shoes, that sells brands like Ecco, Pikolinos, Reiker, Siebel, or similar and try a bunch of things on. The brands mentioned in a comment above will also fit in this category. There's a specific "dressy but comfortable" niche in shoe brands that includes brands like these. Look for more plain, classic styles - something like a standard oxford - for shoes that will look "put together" even when paired well with jeans and T-shirt: these will dress up your outfit overall. Avoid styles too closely reminiscent of sneakers: the rest of your outfit will end up dressing down such shoe styles instead.

Look for two or three tops to wear over your comfortable shirts: a nice but casual blazer (finding one that is not cap sleeve, that doesn't restrict your arm and shoulder movement is the tricky part - they're out there, but may take a while to find), a good cardigan, or pullover sweater with a slightly dressier neckline. I'd avoid jersey/knit blazers - like the sneaker-style but not sneaker shoes, your jeans and T-shirt will end up dressing down such a jacket instead of the blazer dressing up the rest of the outfit. The specific fabric/material in a cardigan or sweater can also make a difference. For the maximal intersection of comfort and dressy, spring for cashmere if you can afford it. If your jeans and comfy shirts are relatively consistent in style and color scheme, just one to three dressier top layers like this will suffice. Try stuff on in little independent boutique stores as well as the upper end fast fashion stores in the mall. Look for independent boutique stores that some women in a variety of age ranges including women in their 30s or so are shopping in, though, not ones only populated by women over 50 wearing full jewelry and makeup - clothes in these latter boutique stores will neither be your style, nor as comfortable the cut and fabrics that you need.

As mentioned above, a scarf is also an easy accessory to dress up an outfit in a more comfortable manner than jewelry. Based on what you said about your workplaces, this may or may not meet your needs - don't wear a scarf if you work with little kids or around machinery that it could catch on, for example. Avoid polyester. Silk, as mentioned above, may work for you (especially if you want to tie it up in some dressy manner that doesn't leave loose ends hanging out). But you can also find some nice longer, drapier scarves in jersey fabric, pashmina, bamboo/tencel, or alpaca if that's more your style. Honestly, though? If your jeans are clean and not ripped, you have a dressy but comfortable pair of shoes on or even a clean pair of hiking boots/shoes (but not sneakers), and a cashmere sweater that's not just a sweatshirt? You'll look fully "put together". If you're unsure about the shoes or top layer - or if it's too warm out for a dressier top layer - a scarf can help, and has the advantage of not costing as much.

As far as a cold weather coat, you can get something sporty but still a little dressier looking from an outdoor outfitter - REI, Patagonia, etc. (you may be able to get a suitable sweater from two paragraphs up, there, too!). The pea coat style isn't working for you - it sounds like you want something that will be waterproof for example, which will also repell dirt more - but if you avoid puffy jackets, you should be fine with any of your options at such a store. If you get your plain, non-graphic t-shirts there too, and if they're not too worn or have holes or anything, and you have a nicer but comfortable pair of shoes on the other end of your jeans, then you're set for warmer weather too. (A boutique where you get a good sweater likely has quite comfortable plain t-shirts too... but wait for a sale so you're not paying $80+ for a t-shirt. A plain short or long sleeve, softer fabric Gap type t will also work well in this overall wardrobe setup.)

If you do want to experiment with dresses or skirts, I'd recommend finding a bamboo clothing boutique and trying on some stuff there? But if you don't need to for work, and if you feel more comfortable in jeans, don't stress about it!
posted by eviemath at 4:11 AM on March 10, 2020

Seconding eviemath's entire comment, especially the recommendations for "nice but comfortable shoes" and Patagonia.

You can save money and shop sustainably by at Patagonia's secondhand Wornwear website.

As for European shoes: There are a lot of brands and styles out there, and the Barking Dogs blog can direct you to the ones that work best for your needs.The blog specializes in recommending nondorky shoes to people with foot problems (plantar fasciitis, bunions, etc.), but you can still wear these shoes even if your feet are entirely cromulent.
posted by virago at 4:56 AM on March 10, 2020 [2 favorites]

PS These $100 Ariat Scout Paddock Boots -- black leather lace-up ankle boots that have a rubber sole and a moisture-wicking lining -- sound interesting, too.
posted by virago at 5:08 AM on March 10, 2020

I am also Team Dress; at this particular juncture, I've acquired two week's worth of a specific high-low dress that looks good on me from Poshmark. It comes in 8 billion colorful patterns, it's going to continue to fit me as I lose weight (this is a big one, I'm approaching 20 pounds down and I want to be able to keep wearing at least some of the same things all summer), it looks good with boots and a cardigan or sneakers or leggings and sandals or whatever. I look nice enough and I'm basically running around in a nightgown. :) (I do have dressier clothes for when I need to go look like "Real Faculty".)

(Once you find things that you like, check out Poshmark along with your local thrift stores. You'll hear varying opinions, but fwiw I've had nothing but good experience and have been getting quality, barely used clothes and shoes for like, 1/5 to 1/10 retail).

If I were you, I might think about ponte pants and sweaters or solid color nicer quality t-shirts as a first step up from jeans and regular t-shirts. There's also those dress pant yoga pants, which might be a good match for you. Also, don't forget that until you get to dry clean only clothes, it all goes in the wash anyhow - so if you wear slacks and they get dirty, so what? They're getting washed just like your jeans would.

sometimes I do feel like it would be nice to wear cool clothes while I'm still young and can try a variety of styles before being relegated to Eileen Fisher et al

Wear what you want throughout your whole life; you don't have to be relegated to anything. One of the delights of my 40s has been having the economic means and autonomy to wear things that I didn't get to wear when I was younger. :)
posted by joycehealy at 5:14 AM on March 10, 2020 [3 favorites]

I'm 50 and in a different place than you in your work life - I'm underemployed on purpose in a different career field than I started in. But I went through similar thinking about how to dress over the past year when significant weight loss meant I had to replace my whole wardrobe. I ended up ditching business casual altogether for jeans and boots/sneakers! I work in archives, which is surprisingly dirty work involving dusty boxes, so it's practical, and it's also a joy to not have a "work" wardrobe and a "regular" wardrobe - I wear the same things on non-work days (and I clean up pretty good for special occasions).

It sounds as though there's no real guidelines where you work - how do other people dress? If there's no external pressure to dress a certain way to appear "professional" - part of me thinks you should just enjoy the freedom!

As a woman, I feel relief at not having to dress to impress so I can just get on with my work. Again, YMMV - I'm not in the public eye, I don't have to meet with higher-ups, and I don't travel for work anymore. But I've always been ambivalent about clothes and generally prefer to be inconspicuous. I love my uniform!
posted by Otter_Handler at 6:10 AM on March 10, 2020 [3 favorites]

Hello, you are me ten years ago!

My transition from boring, comfortable outfits to nicer looking (but still comfortable) work ensembles came in stages.

First I transitioned from jeans and sneakers to sheath dresses and either tights and boots in the winter (comfortable tights exist! I recommend these HeyUU tights from Amazon or these Snag tights -- leggings are also an option and actually more comfortable than tights usually, and warmer so that's a great option if you live in a cold place) or comfortable sandals in the summer (Dansko, Crocs, and Sanita sandals are my go-to brands). Crocs also makes flats that are as comfy as sneakers, I'm wearing some leopard print ones today.

Then I started getting bored of wearing the same dresses every day and I branched out into skirts/tops/cardigans and my trick is to buy items that I know will coordinate with other pieces I already own (kind of like a capsule wardrobe). Here are some outfits (each link goes to an album) I put together this year -- 100% comfortable, but also interesting. One trick I leanred: shirts with interesting necklines are nice because you don't have to figure out necklaces/scarves to go with them, they create their own visual interest.

New wardrobes do cost money, so I don't know that I can help you there.... I'd recommend spending a little more for good shoes (because uncomfortable shoes are horrible -- The Walking Company has a good collection of comfy shoes) and looking for less-expensive skirts, shirts, and cardigans from places like Amazon, TJ Maxx, Old Navy, Target, etc.
posted by rabbitrabbit at 6:57 AM on March 10, 2020 [1 favorite]

Whether you like it or not your current outfits say something about you - and based on your ambivalence I think you really need to think about the message you want to send. That could be "I'm wearing clothes, ok" or it could be "I sure am dressed for work" or it could be "I want the boss role" - that part is up to you. Once you find that part you will be more ok with laying out money on new things because it's all part of your plan now, rather than a whim here or a panic there.

Then it's about the transition - moving to your new you! Try lots of things on. Ask "does this fit what I'm trying to say?" and then when you get the plan going you can be more focused at charity shops or online to build your new look for cheap. I get all my clothes off ebay and whilst they aren't all winners, I spend a heck of a lot less than I used to, and I feel way less bad if something doesn't work after all.

I used to wear jeans and hoodies to work, then I got a job where I had to be smart, so I got a couple of blazers, a couple of dresses, a few tops and two skirts the same in different colours. Capsule wardrobe is the key thing. If you can't wear it with at least 2 other outfits, it's not a winner. Then you can build over time.

Targeting my capsule wardrobe using "is this saying what I want?" check means I can actually pay less attention to my clothes but still look put together.
posted by london explorer girl at 9:07 AM on March 10, 2020 [1 favorite]

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