Weekend Wednesday: How to Wear Shorts as an Adult

75 Comments

1. As long as you don’t wear Bermuda shorts I think you’re fine, they just scream dowdy retiree to me.

   I’m 30+ and I wear shorts all the time, even to my casual workplace on Fridays. I like the 5″ chino shorts from Old Navy or J Crew. I also love the look of white denim shorts – very preppy.

   I was in a serious romper/jumpsuit phase for awhile but I hated having to take the whole thing off to pee.

   1. +1 I generally prefer dresses/skirts to shorts, but 5″ chinos from J. Crew or Target are my favorites.

      1. I also prefer skirts, but shorts are better if you are in the HAMTONS, as men tend to let their hands wander, and shorts are more helpful to protect us against their fingers then skirts. Tight panties help also. FOOEY on men who take advantage of us in bars. They think we are stupid.

   2. I wear bermuda length shorts. It’s what works for my body and comfort level. I may not be 100% on trend, but I definitely don’t look like a dowdy retiree (I have about 37 years until retirement).

   3. Haha, no. Bermuda shorts look great on me.

2. I think shorts look very chic when they’re a bit loose and paired with a casual, airy linen button down with the sleeves rolled up.

   But I wear shorts never. My legs are also pale, super dimply and with lots of imperfections. I find it depressing to look at myself in shorts so I wear long breezy sundresses in the heat and feel much happier. I am all for people rocking shorts but I really don’t think that they’re necessary to stay cool in the heat by any means.

   1. Yes! Sundresses for the win!

3. Find shorts you like. Put them on your body. Boom. You’re wearing shorts as an adult.

   1. +1 this is very dumb.

   2. +2

   3. Yup. Can’t believe this is even a question.

   4. The real topic should be, “how to wear shorts as an adult and not constantly be pulling them out of your crotch.” That is a subject on which I’d like more information.

   5. This was my exact thought when reading the headline. Wear shorts that cover the parts you’d like to cover. Be comfortable.

4. I’m 29, average weight, and wear 5-inch shorts quite often (like you, Kat, I used to never wear them but now have to because I have a baby). I’m not a fan of denim shorts though – I do either chino-style ones or solid-color drawstring ones in fabric like these: https://www.loft.com/lou-&-grey-poplin-shorts/425397?skuId=23171558&defaultColor=0365&colorExplode=false&catid=cat1880002. Not a fan of the trendy tribal-patterned shorts in jersey-like material; those look like pajamas to me.

5. Someone once said on here that only Americans wear shorts. Is this true?

   1. Yes, this is 100% true. In other countries, shorts are for kids.

      1. I think Australians would beg to differ.

         1. All Australians wear is shorts, even in winter. When it gets to summer, shorts are all I wear. Dresses allow the thighs to stick together and no-one wants that!

            1. Yep, still shorts-wearing weather here, even in the middle of our winter!

      2. Which other countries? I regularly see adults in shorts during summer in my northern European city.

      3. Not at all true, at least in Europe. I was just in Paris last week during a heatwave and many were wearing shorts. They’re often more polished-looking than what you might see Americans wear, but people certainly wear them. And the further you go outside of major cities, you’ll see plenty of less polished versions. The stereotype of a German tourist is wearing neutral-colored shorts with Birkenstocks.

         1. Hey, I was there too! Also wearing shorts!

            I’m never complaining about AC in the office again. I’ll take being a little cold at work over feeling like I’m being slow roasted any day.

   2. We wear shorts here in the UK; denim shorts are very popular!

   3. That’s just dead wrong. I’ve traveled all over Europe and parts of Asia and people wear shorts everywhere. Even in Paris.

6. As a mom, I agree shorts are key. I love JCrew and Gap chino shorts. I am petite so 4″ is what I go for. Lately though I have been wearing the Ryan fit shorts from Banana in fun bold prints like this (http://bananarepublic.gap.com/browse/product.do?cid=1086684&pcid=1051528&vid=1&pid=783799002). I find it paired with a simple tucked in tee (I get all mine from Target) and nice flat sandals and bam! I like chic and polished for literally no extra effort and for the same comfort.

7. You can pry my short denim shorts off my cold dead legs

   1. hahaha thanks for the laugh. I needed it today.

   2. May I suggest pants? Then maybe they won’t be so cold.

   3. +1

      I live in Texas. We wear shorts. Sometimes with cowboy boots. World can deal.

      1. The worst is when men wear basketball shorts with cowboy boots. Even the native Texan in me cringes at that.

         1. Ahahaha, yeah, that’s definitely a NO.

8. Is anyone still in the Summer Clothes challenge? I’m wearing an older, sleeveless, white lace fit-n-flare dress (never again–it’s going in the church / Mother’s Day Tea only pile) with wedge sandals that are giving me a godawful blister, and earrings that I just threw in my work trash bin for being gross and green. I think they were a birthday gift from my mother circa 2012.

   FAIL.

   1. I pulled out an long skirt from TJ Maxx this morning because I haven’t gotten to laundry this week yet. Grey with white chevrons, paired with a teal shirt and a sweater in a similar grey. Shirt needs to get tossed (i discovered holes in the front), but i feel good about the skirt!

   2. I’m wearing a navy faux-wrap dress that I bought on clearance at some point and had never worn. Realized when I got to work that the front is a little too low for my comfort, so I’ve spent the day covering up with my desk pashmina, which looks pretty weird in the South in June. Fortunately I think I can fix the dress for the future with a few well-placed stitches.

   3. I’m wearing tan/khaki colored pants, a black shirt from Ann Taylor with a detailed high neckline design, black cardigan, and black flats.

      I wore the pants to see if they were worth keeping and given the fact that I feel like my bottom half looks like a grandma in Florida playing mini-golf, I’ve decided to donate them. At least my hair looks decent today – simple side part and pulled into a bun.

9. I don’t know how to dress my body and I need to step up my game at work when I return from maternity leave. Any recommendations for a good Nordstrom personal shopper in Chicago or suburbs? Someone that can dress a size 14 with broad shoulders and large bust? Alternatively- how does someone with that shape dress? I wear a lot of cardigans but would like to switch to blazers to look more professional but they are so restrictive especially in the shoulder area. Is this a fit issue? Does a properly fitting blazer not hurt in the shoulders?

   1. This had come up in a post a few weeks ago, but try checking out https://insideoutstyleblog.com/ She goes through the various body types and how to dress them; what works and what doesn’t. It might be a helpful place to start!

   2. I totally advocate doing the personal shopper route and finding clothes that work for you when you head back to work.
      But… remember that if you are going to be pumping that may affect your dressing options. I did a lot more separates while pumping because it was easier than my usual dresses. Something to keep in mind and/or to mention when you find yoru shopper!

   3. Fellow transitional sizer here with wider shoulders and bust (but in petite on top of it). Consider going to a “good” Bloomingdales or Macy’s over Nordstroms; I find Nordies to be a difficult place to buy because a lot of their brands (other than Ted Baker, which has to be ordered in my size, and Tahari ASL) just run too narrow, even if I size up.

      Also, for best fit on jackets, consider raglan sleeves as much as possible. Many jackets these days are narrow with higher “set in” sleeves (as they say in the tailoring world). That cut just does not fit if you have a larger bust because the bust pulls on the armholes, making the arms of the jacket incredibly uncomfortable. Raglan sleeves, on the other hand, come into the body of a jacket lower down and often at an angle and avoid a lot of the pulling. Also look for jackets with princess seaming, a swing shape (if well cut – avoid the ones that add pounds to your mid-section with excess fabric), no fasteners (open jackets are extra cute in tweed!) and good darting near the bust (but make sure that the darts are at the right place). I have had the most luck lately on this with Talbots, Anne Klein and (of all things) Kasper (but look carefully at the fabric to avoid their occasional “church lady” vibe).

      The same issues exist with blouses with our build as with jackets. I stick to knits, jewel or boatneck crepe or poly blouses that pull on or button in back, or sleeveless tops as much as possible to avoid the bust issues. Pleating at the neck is your friend. Try Talbots, Anne Klein, Calvin Klein, the Saks house brand, Macy’s house brands, Halogen (depending on cut — some of their blouse in this category actually have too much fabric to be flattering), and Land’s End. I do have a couple oxford style blouses, but those are reserved for fancy appellate court hearings, etc. so that they do not get destroyed because it was a nightmare finding them.

      Good luck. Please report back on what you find because I could use all the tips!

      1. Thank you so much! I didn’t know what half those words mean but I will learn!! Despite reading this blog every day I care very little about fashion. I would just love to have a capsule wardrobe of items that fit, make me look very professional, and don’t make me squirm and tug and fidget with discomfort all day (no spanx, no way, no how).

         1. You are welcome so much.

            Also, remember that each season’s styles may or may not work for you and don’t beat yourself up if that is not the case. Clothes should fit you, not the other way around.

            And if you DO find something that works for you, buy it in multiples as soon as possible. It works with dresses, pants, skirts, tops and shoes. I have five pairs of the same pants from Talbots (two black, two brown, one camel). I have two identical black sheaths because they fit great once I got the bust darted by my seamstress and then I was able to have one above the knee and one at the bottom of the knee to give me options. I have not yet ruled out buying a third one because I am so happy with the first two. I am trying to get to having a “uniform” of sorts and having multiples of pieces that I like, that fit, and that work with the shoes I already have is helping a lot.

10. Step 1: Be an adult.
    Step 2: Wear shorts and stop worrying about it. When it’s 90 degrees with 85% humidity, I am wearing shorts no matter what.

    (Pick a slightly longer inseam, like 4″ or 5″ if you want a short-but-not-obscene length.)

    1. +1 – I like the 4” chino from J.Crew because I feel like they’re a bit longer but not dowdy.

11. Yeah unless you’re wearing VS micro mini shorts with “PINK” across your a$$, or planning to wear 2″ inseam shorts with 6″ platform wedges, this is overthinking.

    Find shorts you like and that hit a flattering point on your leg – 5″ are perfect for me. Wear them. If you want to go for the “shorts and dressy top for dinner” approach, choose a low wedge sandal or espadrille.

    1. Ha! Funny, but true

12. I don’t wear shorts because I don’t really have any casual tops to wear with them. I’m too unmotivated to go shopping for shorts and shirts so I stick to dresses. Once piece of clothing and I’m done.

13. Yeah, but have you ever seen a 30+ year old wearing shorts and thought “that looks good”? No, you haven’t. At best it looks nondescript. At worst…

    I mean, capris and sundresses are very stylish. There are plenty of other options.

    1. Ehh… I don’t think capris are stylish. They’re fine but I don’t think they’re super fashionable.

       Also there are times where skirts/dresses seem too dressy for an occasion, so shorts and a cute shirt are perfect. (I’m thinking some bars in my city)

       1. +1 – Capris are not on trend at all right now. Crops, yes, capris no. And crops are too long for me in hot weather.

    2. Hi, you’re rude.

    3. Capris scream mid-western suburban soccer mom with iced latte in her hand.

       1. +1. I’m a Midwestern suburban soccer mom who drinks iced lattes on the regular. But I will not wear capris; that’s a bridge too far.

          1. don’t drink the ones from starbucks for a while!

    4. Capris are often times not stylish at all.

    5. Actually, I have seen women over 30 wear shorts who look polished and put together.

    6. Oh my! How could I possibly confuse this: http://www.bergdorfgoodman.com/rag-bone-JEAN-Nero-Capri-Denim-Jeans-Black/prod118240024___/p.prod?icid=&searchType=MAIN&rte=%252Fcategory.service%253FNtt%253Dcapris%2526pageSize%253D30%2526No%253D0%2526refinements%253D&eItemId=prod118240024&cmCat=search

       With this: http://www.bergdorfgoodman.com/Hudson-Brix-High-Rise-Crop-Flared-Jeans-Indigo-crop/prod129020009___/p.prod?icid=&searchType=MAIN&rte=%252Fsearch.jsp%253FN%253D0%2526Ntt%253Dcrop%2526_requestid%253D157679&eItemId=prod129020009&cmCat=search !!!

       But no one disputes the main point. You always could do better than shorts if you’re over 30.

       1. “But no one disputes the main point. You always could do better than shorts if you’re over 30.”

          Multiple people are disputing that. I am disputing it. Right now.

       2. The thing is… The cropped flares you linked to are actually in style (see http://www.closetfulofclothes.com/how-to-wear-summers-hot-new-denim-trend-cropped-flares/). I also think that there are many women above 30 who look great in shorts and are very stylish. Shorts could absolutely look better than cropped pants, just depends on the specific outfits.

       3. I think they’re both crops actually. (despite the naming). I always think of capris as falling in between your knee and ankle, hitting somewhere on your calf. Crops are basically like wearing pants when its hot and humid – it’s not any cooler.

          And I think everyone disputes your point.

       4. Yeah, I dispute that point. The idea that I wouldn’t wear shorts for literally decades of my life, when I live in an area with a real summer, is bonkers.

    7. Capris? Stylish? lol.

14. any idea where I can find shorts like the ones in the pic?

15. I’m glad I’m not the only person who thinks about this. I’m realizing that the shorts that I’ve been wearing since high school (I’m 28 now) make me feel naked and exposed, and I just don’t need strange men seeing almost all the way to my bum/crotch region, so I’ve been opting for skirts that go almost to my knee, if not all the way, and keeping an eye out for shorts that have at least a few inches of coverage past my underbum. It hasn’t been easy. Also, I aim for high-waisted shorts that I can tuck a nice shirt into, as well as hiphuggers I can wear with t-shirts when I want to be casual.

    I don’t know why, but in the past couple of years, I’ve felt compelled to cover myself more. Longer skirts, higher necklines, sleeves instead of sleeveless, I’ve even thought of getting those lace trim shorts to wear under dresses for added “protection” against, I dunno, pervy dudes I guess.

    1. It’s probably a by product of working in an office. When I got my “adult” job and started to be more covered up for work I became much more aware of my bare skin in my off time. A lot of it was really subtle but I became much more aware of low tops and thin straps and short skirts and all of that. I also notice the difference in how certain men stare when I am dressed in something more revealing, which I don’t think I noticed as much when I was in college/law school and it was more the norm.

       1. This. After a while of working in the office, my idea of “appropriate” became skewed toward *office* appropriate. Like AIMS, I became more conscious about hem lines, necklines, and the like.

          That’s not to say all my clothes are conservative, but my instinct is to go for the demurer option.

       2. HUH, that might be it! I mean, most of the places I’ve worked have been super casual, no real dress code, but between lurking here and over at AAM I have been made aware that thighs, cleavage, and shoulders are generally supposed to be covered up at work.

          I also think it’s a product of being in the city, and being around so many strangers all the time, many of whom are men, and there’s the looming threat of street harassment and blatant oggling. Maybe this isn’t fair, but I just don’t like the thought of strange men taking pleasure in getting to see certain parts of me. Maybe it’s a combination of those things. And I now know darn well what happens on windy days!

       3. I agree on being more conservative after you start working. I work in a healthcare company at the corporate office which is pretty conservative. On top of that my boss and several male coworkers are LDS. That adds a whole other layer of modesty to the situation!

16. I highly recommend the linen shorts from Athleta, with the 5″ inseam. The fabric is soft and washes up great. They’re on the pricey side for shorts, but a good way to use my Gap rewards.

17. I just asked my husband the other day if I was too old for shorts in a moment of irrational panic and he told me I was being ridiculous. I agree with the commenter who said find a length that looks good on you. That’s going to depends on your body shape and comfort-level. Bermuda shorts look terrible on me and I am way more self-conscience in those even though they offer more coverage. Granted I’m in my early 30’s but I prefer a 3-5″ inseam. I don’t own jean shorts because I owned a lot of them in the 90’s and just can’t figure out how to wear them as an adult without feeling like I’m in high school.

    My most “polished” shorts look is a pair of army green linen-ish shorts with a tie belt (Loft?) that I wear with an looser open-knit, beige/white, sweater and and a heavy gold chain statement necklace. I either wear it with beige/white espadrille platforms or flat beige sandals, depending on how dressy I want to look. I always gets compliments when I wear the outfit, especially about looking “fancy,” so I think it’s possible to look chic even in shorts. I think white can also dress up shorts–either white shorts or paired with a nice white shirt. I have a pair of white eyelet shorts from BR that can be dressed up to a degree. I mean, they ARE shorts so you can only get so dressy.

18. I would (almost) rather pass out than wear shorts because of some lingering 7th grade gym insecurities (yeah, I should get over it) so my feeling is “if it’s hot enough to wear shorts, it’s hot enough that anyone judging me for not looking sufficiently put together should get a life.”

19. I think the key to shorts past a certain age is having enough volume around the hem so they are loose on the thigh, like the photo. The shorter they are, the more volume you need (though I agree that a slim cut Bermuda is not on trend at the moment).

20. This summer I bought Athleta’s Midtown Short and can’t recommend it enough.

    athleta.com/products/midtown-short-P708303.jsp

    The fabric is soft and comfortable, so they feel more like running shorts (especially in super hot and humid DC summer weather) but their cut/style makes them look a little more polished. I am 5’7 with long legs, so I opted for the “tall” length (a 6″ inseam, rather than the regular 4″ inseam).

21. I am in my 30s and have one pair of shorts. They are denim cuffed shorts from Ann Taylor Loft I bought a few years ago. I sized up so they are a bit loose and therefore comfortable. My biggest complaint with shorts is how they would ride when you sit down, how my pale thighs would be on display when sitting down, and how my legs stick to the chair when again, sitting down. Sizing up has definitely helped, but I really only wear the shorts when it is unbearably hot and I need to run errands. Otherwise I stick to denim cropped jeans or cropped black pants. I find they are comfortable enough.

    I used to wear dresses a lot on the weekends but now since I like wearing canvas sneakers, it is harder to find dresses the sneakers go with. Plus, I hate sleeveless dresses, shirts, etc. and it is hard to find a dress with a short sleeve. I will say that dresses are probably the coolest thing to wear (temperature wise), even cooler than shorts, because you get that breeze going.

    And for all that is holy, please don’t wear shorts that come all the way to your knees. Nothing is less attractive or feminine. Switch to a cropped pant, linen pants, a dress, skirt, anything but that.

22. Love the underlying message that you’re trying to convey here. Crossing into your 30s shouldn’t hold you back at all. To answer your question, the favorite shorts I wear over the weekends is this botanical floral fuchsia one.

23. Nice article! Shorts are my favorite outfits. I like this article so much. Thanks for sharing.

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