Going Out Clothes After 25

going-out-clothes-after-25Today was supposed to be part two of our suits roundup but, well, it’s taking too long and I don’t want to slap something up half-finished. So here’s an interesting question that came up yesterday in the comments — can you wear denim for going out clothes after 25? Is there an age limit, or is it just not cool to do anymore? What are your favorite things to wear for going out? (Update: here’s our latest discussion on going out bags, too. Also note: we’ve talked about what to wear when you’re going out with colleagues.)

Pictured: jumpsuit / leather pants / dress 

For my $.02, I still occasionally wear denim for going out, but our date nights are usually pretty casual, as are girls’ night outs as most of my good friends have small kids at this point and we’re either too tired to paint the town red, or because someone needs to stay at home for lack of a babysitter so we go over there instead.When I was dating I never liked to wear dresses on early dates — guys reacted weirdly as if I had “dressed up” for them, and when things started to get physical, I found dresses too binary, if that makes sense — they’re either on or they’re off. (Interesting to ponder: in Gone Girl, Gillian Flynn explained “the Cool Girl,” which to my mind always meant jeans + cool top — dresses or a jumpsuit would seem too fussy to me.) Of course all of this is just more information — what ultimately matters is what you want to wear when you go out, not what your partner wants you/expects you to wear, or what other friends or some mythical Cool Girl are wearing.

So let’s hear it, ladies — what do you like to wear to go out? Do you dress differently than you did in your early 20s for going out?  What are you looking forward to wearing for summer evening outings?

Pictured: maybe I do need a place to wear this jumpsuit, these leather pants (40% off!), or this off-the-shoulder sheath dress to… 

Psst: we kind of got into this in our discussion of what to wear for grad students going out on the town with future colleagues. Also — some commenters below noted that heels + jeans + nice top looks dated to them, which made me think of this Buzzfeed video, “100 Years Of Fashion In Under Two Minutes” — here’s the best gif from 2005. Totally my going out look from 2003-2008(ish) for sure!


Can you wear denim for going out after age 25? The question came up in the comment section, so we had a full discussion of it, with lots of women (age 25-45) sharing what they wear for going out clothes, whether on dates, with friends, for casual nights out, fancy nights out, and more.


  1. Anonymous :

    Going out to dinner? Yes, depending on the restaurant of course. Going out to a bar? No. But I think that’s just based on what’s in style right now. In 5 years it could be all flared jeans and pointed-toe pumps again. I tend to wear dresses, but I’m married and my husband doesn’t see dresses as “dressed up” (but I know a lot of men automatically have this association!).

    • When I was 25, I could wear alot more stuff then now.. I had a pair of tight leather pant’s and wore them with leather boot’s. In DC therewas a cowboy bar and restrunt near 19th street where men bought me drinks and squeezed my tuchus. I NEVER let them put there hand’s anywhere naughty, tho they sure wanted to. FOOEY on men who do that and with dirty hand’s nonetheless! Even Sheketovits I made wash his hands before he did anything. But NOW I dress more conservative, and no tight jeans, primarily b/c my tuchus is big. FOOEY!

    • I will never let my bootcut jeans and pointed toe pumps die. I will be that crazy dated woman people side-eye.

  2. I can relate to this. At 36 crop tops and minis are out, but with AA cups, a low necline is not my first choice, though I am comfortable exposing more leg and abdomen. With my hippie or hipster friends IDGAF, but with the more corporate friends in more upscale settings, it’s a challenge.

    • I’m 35 and I still wear crop tops, although it’s more of a slight crop (so just a sliver of skin).

    • AlsoSmallUpTop :

      For you? Cowl neck? Are those still in? I have no idea.

    • Anonymous :

      With a chest that small, you get to wear all the complicated tops that you can’t wear a bra with, the ones that everyone else with a large chest dreams of wearing one day but knows it’s futile.

  3. In NYC and DC, I still wear skinny jeans, heels, and a cute top. I’m 34 and single.

    I live in dresses both at work and for casual Saturdays, but for going out, I like the laid back vibe of jeans that says “I’m not too high maintenance.”

  4. Anonymous :

    I have a kid and am nearly 40 years old, so these days “going out” mainly consists of casual dinner + movie (jeans and cute top) or concerts, ballets, and plays (M.M. LaFleur Rachel dress or dressy top and cropped black pants with dressy sandals). I am rarely in a bar other than a hotel bar or our neighborhood “bar”/restaurant places where we take the kid along. We tried going to a “real” bar once recently and felt silly and out of place.

  5. Since when are jeans not acceptable? I always wear black/dark blue skinny jeans and boots until it’s too warm for boots then I usually switch to flat sandals. I avoid heels like the plague but that’s my personal preference. I’m in Chicago so warm weather going out attire really only works from like July-September. Even in June its chilly in the evenings.

    As far as finding cute tops, I find them everywhere. I’m 27 and still buying things from Forever 21 though I’ve found myself liking less and less of their inventory. Part of it is simply bc I hate the 90s trend resurgence and 90’s or not I don’t do crop tops and I hate hate hate these deep-v lace up necklines. Anyway, I have some real gems form F21 that I love and they’ve held up nicely.

    I’ve accumulated quite the stock of cute going out tops.. I need to cut back because I do find myself getting dressed up less and less. Part of it is because so much is sleeveless and Chicago is so cold I don’t want to wear those for most of the year.

    • ChicagoToo :

      I hear you on sleeveless tops being too cold. After a decade in this city I finally have a good collection of cute (and paradoxically) sometimes low cut sweaters.

    • Anonymous :

      Seriously, I don’t want to live in a world where jeans aren’t acceptable for going out. That’s just crazy.

  6. TO Lawyer :

    I think it depends on where you’re going and how comfortable you are in jeans and/or dresses. There are a lot of hipster places here so I feel overdressed in anything besides jeans. I like leather leggings as an in-between between jeans and dresses. I also still like dresses and try to wear them whenever I can. It’s funny though – my ex always thought dresses = me being super dressed up but trying to create a cute outfit out of jeans and a top always seemed like a lot more work than just putting on a dress.

  7. MargaretO :

    I am in my mid 20’s and I think the jeans with heels and a sparkly top look is super dated looking, for women of every age. It feels very Jennifer Aniston circa 2005 to me. I wear denim/leggings out to casual bars or parties all of the time, but if its a dressy enough outfit that I would consider wearing heels with it, I wear a skirt or dress. My go to at the moment is an a-line mini skirt with a cute top, I’ve been wearing a couple of the new off the shoulder ones a lot.

  8. Depends on the vibe of the place I’m going to. A nice restaurant with hubby or the girls, a dress and heels. Crowded rooftop bar, jeans, se*y top and wedges. I’m 38 and still wear jeans but have going out jeans that are fitted and in a darker wash than my usual jeans.

  9. Diana Barry :

    “going out” right now is going out to dinner with my DH, so I almost always wear jeans and something, but in the summer if it is warm enough I’ll wear a maxidress. I am always cold so for 6-8 months out of the year I am wearing a sweater if we go out.

  10. Hipster Nation :

    The idea of wearing a dress out to a bar or restaurant is completely foreign to me in my totally laid-back hipster town. Seriously – if you’re dressed up you’re a tourist. But then I went to Atlanta and was floored by how people were dressed for just a random downtown restaurant. To me they were as dressy as what I’d wear to a wedding!

    • Mrs. Jones :

      I live in Atlanta and rarely see anyone dressed up for dinner! Funny.

      • I think that what we register as “normal” registers to other people as dressed up, maybe? Like, I was at a restaurant in Buckhead earlier this week (on a weeknight) and bar was packed with women in tight white jeans, high heels, drapey tops and tons of jewelry, jumpsuits (and high heels and tons of jewelry), minis and off-the-shoulder tops (and high heels and tons of jewelry…I mean, it was Buckhead), and that is normal for much of Atlanta to me, but I’ve definitely had friends come visit and express surprise at how dressed up people were.

  11. Question for the tall ladies: Did you wear heels when going out as a singleton? If so, how tall did they make you and did it change the way men interacted with you?

    • Yes. Makes me 6′

    • I always did. Can be around 6’1 or 2″ in 3-4″ heels. I figured any guy who wouldn’t talk to me because I’m tall in heels is someone I’m not interested in knowing anyway.

    • Marketingchic :

      Yes- 3″ heels put me at 6′.

    • I rarely did but mostly because they kill my feet and my boyfriend is my height. I’m 5’11” and wore heels more often in college that made me 6’3″-6″4. They did change the way men interacted with me. It brought in more maybe tall fetishists?.. shorter guys that would constantly exclaim how much they loved my height. More importantly though it singled out the much taller guys. Excluding the much shorter guys that talked to me, the rest were like 6’3″ and taller which I loved. But it also draws in the really tall guys as well lol because you’ll be the only woman in the bar they can almost see eye to eye with.

      I had this discussion with an even taller female coworker (at a bar) and she even said to me “just watch. that 6’7″ guy is going to talk to me because i’m wearing heels”. she was spot on.

    • I’m 5’7″ so on the taller side, and heels would bring me up another 3″ or so. I’d wear them occasionally, but I HATED being tall at a bar. I felt that guys always liked girls who were 5’3″ or so. Something about being little. Was a huge self-esteem thing for me in college.

      • Worrywort :

        Really? I’m 5’2″ and literally every guy I’ve dated has told me they wished I was taller — oddly, a lot have specified that they would have preferred I was 5’7″.

        Too sad I can’t handle the foot pain enough to be 5’7″. :)

    • Anonymous :

      I did. I like being tall, it makes me feel like a model and heels just emphasize it. I think people always liked it.

    • Yup , heels put me at 1,80-1,85. Which (hehe) scared away a lot of short men. Didn’t really bother me though as I have a quite distinct ‘type’ :D

  12. In my early 20s, I liked to go to dive bars in jeans and a white tank top. Sometimes I wore a black tank top. I haven’t changed too much into my 30s (just better jeans and tops maybe?) but now I am sometimes forced to go somewhere a little shmancy (or cheesy) for a friend’s birthday or whatnot and I never know what to wear to that and usually just wing it by amplifying the accessories. For summer, I really like blingy flat sandals. I feel like you can wear something easy and if you have awesome shoes, it will all work. I also wear a lot of dresses but dress them down a bit with flat/low heeled shoes (boots or sandals) and other accessories.

  13. Unrelated but couldn’t resist, why would anyone buy this? https://www.nordstromrack.com/shop/product/1667608/eileen-fisher-sleeveless-silk-shirt-regular-petite?color=MARBLE

    This looks like me on a bad day after I’ve spilled coffee all over myself.

  14. The idea that I’m too old to wear jeans on a dinner date with my husband (I’m 33) is laughable to me… but is that not what we’re talking about as “going out”? I have no idea what is or isn’t appropriate for late-night bar hopping because my favorite activity at 10pm is sleeping.

    Typical Saturday dinner look for me:

    Fall/spring: skinny jeans (gray being my new favorite), pointed toe flats, silky blouse with either a deep V or unbuttoned one more button than normal.
    Winter: Swap the pointed toe flats for boots or booties, and swap the silk blouse for a cozy-sexy sweater. Occasionally wear leggings and sweater dress instead.
    Summer: Much more likely to be in a maxi skirt and pretty silky top, but occasionally white jeans and slouchy tee.

    • I’ll add that the “jeans plus sparkly tank top plus monster heels” look feels very early 2000’s to me — it’s the slouchy-sexy tops and flats that update the look IMO.

    • I’m 40, and my Dh is pretty much always dressed the most casually in the room. He’ll wear a tie if he has to, but only when necessary. So I do the skinny jean, silky top very regularly. In the summer I like a cute dress, but the AC often gets me. It works doe our very casual lifestyle.

  15. MargaretO, above, says she thinks a dressy top with jeans looks dated, circa 2005. Interesting. Do others agree? What other looks strike you as dated? I think I may be too old now to notice!

    • I wear what I like and what I think suits me. Which IS dressy jeans, cute top and heels.

      I’ve realised in the last year or so that in the eyes of “kids” I’ve passed out of the “youth” category and into that “not quite sure where you fit in” stage. I’m not near middle age but I’m definitely not 20s either. Now I feel that I’m not being compared to the “kids” is both disappointing and a relief as I can wear whatever I damn well want. :)

    • I found the comment interesting as well.

      I certainly think a *sparkly tank top* is a dated look (and I can remember the ones from my own 2005 closet), but I don’t think there’s anything dated about black skinnies, killer black heels (I have a sexy pair of black snakeskin d’orsay heels that are my night out go-to), and a blousy top with geometric cut outs. Add eyeliner and that’s a great look.

      I think it’s hard to tell from words alone on a message board.

      • I don’t know if it looks date year-wise (like 20oX) or age wise, like I just wouldn’t wear it now in my later 30s but I did in my early 20s.

        • I have some sequined tops that I think are very tasteful and were purchased in the last 3 years. I do primarily limit them to winter because for whatever reason I equate sequins and sparkle with cold weather (snow) and the holidays (christmas/NYE)

    • I think I sort of get what she is saying. I think black pointy-toed heels, a tank top or top of some kind with sequins or the like, and flare/bootcut jeans was my uniform from roughly 18-23 (i.e. from 2001-2006).

    • This video may help – I totally wore the outfit from the aughts and agree it looks dated!


      • MargaretO :

        Yes this is exactly what I was picturing! I see toned down versions of it around that still look dated to me – no embellished pockets on the jeans, less shiny top. It’s just not something I would wear. But I am mid 20s and single and go out a lot. I think a lot of it is the heels with everything look – I basically only wear a heel above 1 1/2 inches or so to very formal events. Most women I am friends with wear either flats or short chunky “grandma” heels pretty much all the time. I will admit I run in a pretty “hip” fashion conscious crowd, but I’m in a very laid back city and mostly go to divey bars.

    • Anonymous :

      I agree with her – it’s out of style to wear to a club or “out” (which doesn’t mean going on a dinner date with your husband to a nice restaurant). You used to wear jeans (or black pants) and a fancy top and platform heels to a club, but nobody really does that anymore. The odd time or two I’ve seen a lone woman in skinny jeans among a gaggle of friends, she really stuck out. I don’t think it’s necessarily dated to wear a current pair of dark skinny jeans and a nice top out to a restaurant, but it’s also probably not a fashion-forward look.

      • So if no jeans or black pants then what? Leggings? Dress? I tend to wear more leggings and boots than jeans these days personally. But I remember when leggings were a big no too.

        • Anonymous :

          For a club, those shiny leather-like leggings are still done. Mostly though it is all dresses and skirts.

      • Yeah I thought black pants was an early 2000’s thing. Before I was “going out”

  16. I’m married and 28, but for going out to dinner at a nicer restaurant I’m wearing dark or white jeans, nice top that I can’t wear to work (like it shows cleavage or has an interesting back or is kinda see through) and high heels. Or in the summer I’m wearing a pretty sundress with strappy sandals (not flip flops or my trusty birkenstocks, though). I actually just bought this dress this morning that I’m pretty excited for summer dates: http://www.loft.com/tie-neck-dress/396247?skuId=20811686&defaultColor=1611&colorExplode=false&catid=catl000013&_requestid=555081

    Ways I dress differently for dates than I did in my early twenties: no flip flops or hooded sweatshirts in public. I just feel shlumpy in them now. I didn’t do a lot of partying, even in my early twenties so I guess that shows there. :)

  17. Senior Attorney :

    I’m 57 and wear skinny jeans or flared jeans (dark denim or white), cute top, and heels. For dressier I’ll change out the jeans for skinny blank pants.

    • +1 Yeah, I don’t get the idea of not wearing denim for x if you’re over a certain age.
      If the situation isn’t appropriate for denim, sure.
      If you don’t like or don’t want to, sure. But imaginary line in the sand? Not so much.

  18. My friends and I lament about how all we buy is work clothes (or maternity clothes, in some cases) these days, and we never have anything to wear to “go out.” Similar to others commenters, when we go out it tends to be drinks and dinner (not a lot of bar hopping or house parties happening anymore at 33), so most places nice jeans, black ankle pants, leggings, maxi dresses or a skirt (of the stretchy material type), are usually the name of the game. +1 to living in Chicago where weather makes it hard to wear sleeveless stuff w/out a cardigan/kimono type thingie. I wear business casual/formal five days a week, and I’m so conditioned to know what that looks like I feel like a moron when trying to put together a “going-out” outfit on the weekends. I pretty much have five outfits on rotate.

  19. My two cents from Ireland – at 35 I feel much more comfortable in jeans & a silk blouse or slouchy tee with heels or dressy flats than wearing a dress – I only wear dresses to weddings! Possibly because I’m petite and feel at 4’11 wearing a dress jus feeds into the ‘little girl’ image I want to avoid. Who says jeans are not ok for going out over 25? Wear what you feel good in!

  20. Pretty Primadonna :

    I’m 35. Dress and heels or cute sandals the vast majority of the time. Never jeans, but sometimes leggings. Even when I was a 20-something.

  21. I am in my mid-50 and generally wear dresses or skirt & top, always heels and black or nude hose (if I wear them at all).

  22. I’m in my mid-twenties and rarely wear jeans anymore, partly because it’s difficult for me to feel pulled together in jeans and I can achieve that look much more easily by wearing other pieces.

    If I’m having dinner or cocktails with girlfriends, I’m usually in my favorite black Paige skinny pants, a low cut silk cami, leather jacket and open-toed ankle booties. For date nights with a boyfriend, I wouldn’t hesitate to wear a minidress. For date nights with a non-boyfriend, I’d wear this: http://www.revolve.com/parker-mora-top-in-black/dp/PKER-WS328/?d=Womens&sectionURL=http%3A%2F%2Fwww.revolve.com%2Ftops%2Fbr%2Fdb773d%2F%3Fnavsrc%3Dsubclothing&sessionID=346043647. To me, shorts say fun but not trying as hard as a dress. Writing this post has made me realize I spend entirely too much time thinking about clothes.

  23. wishyouwerehere :

    You are never too old for jeans in Denver. Which is one of the many reasons we all love to live here.

  24. Dark Denim and a cute tee or blouse with flat is the norm here. Or leggings and a tunic. Perosnally I like dark denim, tee and leather jacket (fitted and colour).

  25. I’m in my early 20s (23), but graduating law school. So most of my going out events are with people in their late 20s/early 30s. I wear dark skinny jeans, black heels or flats, a nice sleeveless shirt or cami, and a blazer or jacket, or a fit and flare dress and a cool cardigan or blazer. I tend to focus more on makeup than outfit- half the time I have to wear a rain coat in my city (or make rain boots look cute…), so it’s all about the makeup.

  26. HonoluluBei :

    I’m 40. Here in Hawaii going out is a nice pair of slippers/sandals and resort wear by the beach. Or, in the city night clubs cocktail dresses or glam hooch for the young at heart and a little glitzy pair of heels. The younger crowd is in bottom bearing cuttoffs at the 20-30 something bars. Or some sort of club wear going out. Or bikinis at the beach–all ages.
    Cost of clothes is not as much of a matter as long as you look great in them.