This right here. And I’m into style, not fashion/coolness. You can look classy without being on top of every trend. I’m in my 40s. I did give up on style during college and for a number of years afterwards, but later on realized the value of presenting an appealing look when possible.
I have been fashion-impaired my entire life.
First day of 9th grade (sept 1968), I thought I was so stylin’ - I’d made myself a pink dress and I had a matching pink hat like the blue one in this pic. Oh, and I had enough fabric left over that I made a matching bag. Yeah, I was making a fashion statement… :rolleyes: I also owned a flowered shirt with white collar and cuffs. Yeah!!!
Some time shortly after that, I got all daring and bought a mini-skirt! :eek: It was lime green with 2 rows of faux brass buttons down the front from waist to hem. I bought it with my own money and I thought I got a great deal. It barely survived the washer - really cheap fabric. I was bummed. 
Variously over the years, I tried palazzo pants and bolero vests and hip-huggers and leggings, always with disasterous results. I’m pretty sure it was in my early 20s that I decided I wasn’t going to even pretend to follow fashion. I wore what I liked, which included the comfort consideration. Even now, if I have to dress up for an occasion, comfort is a primary consideration.
I won’t go to a wedding in pajama pants and flip-flops, but I’m not going to be wearing heels either. I will be presentable, perhaps even attractive, but I will be comfy, by golly! 
I dress just as much for cool as I ever have, which is to say, almost not at all. I used to like statement and/or character T-shirts which, while far from high fashion, at least are a type of fashion. Now, while I shy away from those today, I do factor looks into my clothing when choosing a hat or a coat, however, being in Florida cuts down on the number of times this counts.
ETA: actuall statement/character t-shirt are not mutually exclusive versus comfort: my most comfortable t shirt ever is a very heavy thread count Anberlin tee. However, sometimes I do choose a flat cap over a toque because of looks rather than comfort.
I don’t see the contradiction. Tunics paired with leggings and flats are very fashionable right now. That’s practically pajamas.
When I had my daughter at 30 things went downhill, just for the wash-and-wear spitup kind of reasons, never mind the gained-weight kind of reasons. I still sometimes get inspired in the springtime and wear something cute when I get a chance to go out without my daughter.
I am looking forward to being about 60 and being able to wear the frumpy heavy sweaters and stuff that are comfy and let me stop thinking about my spare tire, without my husband grumbling about the frump.
I was around 18 when I stopped caring what others thought about my clothes. Now when I dress up, it’s to look nice, not be stylish.
I have, for as long as I had input in my choice of attire, been buying and wearing what suits me–whether that was my all-black high school and early college days or my current predilection for straw hats, loud hawaiian shirts, geeky t-shirts, and generally deliberately ugly stuff. At work things get a bit more subdued–I have my shirts tailored, and I like button collars with french cuffs. And Millenium Falcon cufflinks. 
Wow I actually agree with you on something. Weird.
They don’t have to be mutually exclusive, but I’m sure I’m not the only person who has worn a particular piece of clothing or shoes that weren’t comfortable because at the time, looking stylish was more important.
I’m kinda confused by the OP. What else do you wear to a concert except jeans and a t-shirt? I’m going to see Clapton in May (in LONDON–I live in Chicago) and plan on wearing jeans and a t.
Seventeen, perhaps. I’ve always been fashion-unconscious, but I take care never to slip into slovenly territory. My wife had an extraordinary ability to look dignified in nearly any setting in just a long sleeve shirt and a pair of dark jeans. Never quite grokked that skill, sadly.
I’m 28. I’ve dressed for comfort all my life.
A fashion-conscious friend of mine said I have my own style. 
^This. But the OP’s idea does seem pretty typical on the SDMB.
How are you defining “nice” and “stylish”? They mean pretty much the same thing in practice, don’t they?
Looking good absolutely does not have to be uncomfortable. Wear clothes that fit properly and 75% of potential discomfort is gone. I’m wearing a dress, cardigan, stockings, and flats today – I look cute and I’m so comfortable I could take a nap in these clothes without a problem. I’d take off the shoes first, though.
Ah, the ladies may get this: I was meeting for the first time 2 of the wives of my partner’s business associates.
One in a long dress with a little bolero jacket, and one in jeans.
Always. Or at least since I’ve been dressing myself.
Since when has boots, jeans, and a t-shirt not been fashion-cool?
Now that I’m in a professional, office environment I’ve moved to khakis and short sleeve button down shirts to work, but that’s really just the office-casual version of jeans and a t-shirt. There’s a lot of variety and good-looking options in short sleeve button down shirts. I still rock the boots.
You’re supposed to stop caring about fashion? :dubious:
No, seriously, it depends on the occassion. Sometimes it calls for jeans and tshirts, sometimes skirts and heels. And sometimes I like wearing non-dressy skirts and flats. Or jeans and stylish tops. It all depends on my mood.
Of course. This *is *the SDMB we’re talking about.
18…just part of leaving high school behind for me.