Reader Request: Stylish Shorts

How to pick flattering shorts

Beautiful Anne sent this request via e-mail:

I just watched a blurb about shorts for every body type on the Today Show, except that they only showed 4 models and they all looked about the same to me, so it wasn’t very helpful. Can every body type really wear shorts? I know you tend to wear more skirts and dresses, but sometimes a skirt isn’t quite appropriate. With summer kind of approaching here in the Midwest, I’d be interested to see your take on this.

This is quite a challenge to me, my friends, as I probably wear shorts twice per year. But I know they’re a summer staple for many, so I’ll weigh in on Anne’s questions as best I can!

Can every body type really wear shorts?

But of course! Whoever said that certain body types should avoid shorts is a Clothing Tyrant and should be immediately overthrown in a bloodless coup. If you like shorts and feel comfortable in ’em, wear ’em. Find a style that suits you, and sport them all summer long. The end.

What’s the right length for me?

It will all depend on how long your legs are overall, how long your thighs are in comparison to your torso, how much thigh you want to share with the world, and how important leg-lengthening is in your personal hierarchy of figure-flattery priorities. But in my humble opinion, a hem length at least one hand’s width above the knee is almost universally flattering. (Did I mention almost? Only you and the dressing room mirror can decide for sure.)

Longer shorts such as Bermudas are great in the coverage department, and if that’s your objective, then by all means go long. But remember: A SKIRT that hits at the knee allows the observing eye to imagine thigh shape relatively freely. A pair of loose shorts that hit at the knee may trick the eye into thinking your thigh fills the entirety of the pant-leg. If you can, show some knee and a wee bit of thigh above the kneecap because it reveals more of your true shape.

Notice how just a few inches in length can make all the difference. The Bermudas at left are totally cute, but the patterned shorts at right give a better idea of overall leg shape. Both via L.L.Bean.

Higher than a hand’s width above the knee can be super flattering, too, so go shorter if you’d like. How short is going to depend on your comfort level with your upper thighs and your personal preference. But I’m gonna come right out and say it: Shorts that have an inseam of 3″ or less aren’t my favorite, even on lithe teenagers. I just plain don’t like how they look. Shorts that are, in essence, panties with a zip fly make me frown since they look neither comfortable nor chic to my eye.

Not my favorite. Via Bebe

Shops like J.Crew and Land’s End offer shorts in a wide variety of hem lengths, so you can truly choose how long or short you’d like your pair within a few inches. You’ll find 3″, 5″, 7″, 9″, and 12″ hems on these sites. Talk about selection!

What’s the right style for me?

Again, only you can truly make this call. But here are a few things to keep in mind:

  • If you’ve got a small waist and a spare-tire belly, shorts with pleats that hit at your natural waist will emphasize the tire. Flat-front styles that sit two fingers below your belly button won’t pooch as much.
  • If you’ve got no curves and wish to emulate curves, embrace pleats. They’ll flare out a bit and give the impression of volume where there is none.
  • If you’ve got no curves and a short torso that you wish to lengthen, try the loose, hip-slung approach.
  • If you want to emphasize your curves, shorter shorts that hit at your natural waist will do just that.
  • If you’ve got no waist to speak of and carry weight in your midsection, flat-front styles that hit at or just below your natural waist will create a balanced figure. If you’ve got slim legs and want to show ’em off, by all means choose a shorter hem length.
  • If you’ve got a long torso that you want to shorten, try high waists, paperbag waists, and belted styles.

How should shorts fit?

Semi-constricting hems are sometimes unavoidable when you sit down, but I still believe that shorts should not cut into or subdivide the thigh when you’re standing. If you go for a style that fits closely, make sure it has some stretch.

And, as is the case with ALL bottoms, shorts should not cause your midsection to spill out over the waistband. When you try on shorts at a store, bring a fitted top into the dressing room, too, so you can be sure they’ll sit flat and quiet against your midsection.

What else should I consider?

If you are concerned about leg length and proportion, shoe choice is extremely important when constructing a shorts-based ensemble. (See an entire post on this topic here!) Take a peek at these images from the Nordstrom website for a quick lesson:


Here we’ve got a versatile length short with a great fit, but those flat sandals that hit at the ankle bone shorten the calves and make them look thicker.


Now, these t-straps also hit at the ankle bone, but since they include a wedge heel, they’re far more lengthening than their flat compatriots above.


If you can’t imagine wearing heels or wedges with something as casual and knockabout as a pair of shorts, a shoe with a nice low vamp will still elongate your gams. I’m not a huge fan of flip-flops, but these make the model’s legs look marvelously long: It’s nothing but skin from just above the knee to just before the toes.

Hope that helps!

Top images courtesy Gap.

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details. Sustainable options are either used, handmade, made in the U.S., artisan made in non-sweatshop conditions, or made using sustainable/fair trade practices.

Originally posted 2010-06-08 05:30:00.

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34 Responses to “Reader Request: Stylish Shorts”

  1. Sal

    From Jessica from yesterday: Having lived in Florida for the past ten years, it goes without saying I lived in shorts for most of the year.

    I'm about 5'6", 150 lbs. Some of my favorite pairs of shorts hit me mid-thigh. My very first outfit for BLACK OUT week is a pair of shorts! (Pics on my blog later tonight!) When I wear a pair of mid-thigh shorts I don't pair them with heels, I go for flip flops or flats. Longer length Bermudas I go for wedges with as I feel Bermudas, as cute as they are, make me look bottom heavy, so I try to make my legs look longer.

    Old Navy really stepped up their game this year when it came to their shorts. Prices, style, selection, construction and hem-length.

    I don't wear denim shorts, though. I guess for me, denim shorts are more of a kid thing and they also conjure up a whole host of Daisy Duke images. Not to say they're unflattering, but for me personally, I would rather wear a long pair of jeans or a denim skirt over a pair of denim shorts any day.

  2. Sal

    From Rad_in_Brookyln from yesterday: I'm also a partisan of the fact that every body (and thus everybody) can wear shorts!
    I am a fan of buying cheap summer weight pants to the thrift store (or using pants you already own that are tearing at the knee or worn out at the hem) and cutting them yourself to a desired length. Start long and then cuff. Repeat if you'd like them shorter.

    I'm actually wearing a pair that I thrifted (for about $2) today:

    These are another pair from an older pair of dress pants:

    Also, if you'd like to get a nice hem, you can just take them to a tailor or do a few hand stitches by the existing side seams.

  3. Sophie Miriam

    I'm with you on short shorts. Best rule I ever heard–the shorts should come down past your fingertips when your arms are at your side.

    Other than that, I have no comments. I wear shorts one day a year, when I have to jump into knee deep water to clean out our pond. I keep one pair of short shorts (yes, I know, they stink, but modesty or looking good are not the point when cleaning a pond) for this purpose.

  4. orchidsinbuttonholes

    I have a hard time finding shorts that fit me properly and am usually far more comfortable in skirts. This spring I found a great pair of walking shorts – they're just-above-knee-length, have a bit of stretch in them, and they're by Vince. They go with pretty much everything. So far I've only worn them with ballet flats, but I think I'd wear them with wedges as well. The heels-with-shorts look just isn't me, although I've seen it done quite well.

    Great post, and I can't wait to read about other short favorites!

  5. Kendra

    Great piece, Sal!! I have NOT been a big shorts wearer, and went years without wearing them. But this year I found a pair I like and have worn the crap out of them in just a few weeks.

    My frustration this year has been that so many stores have been stocking online cut off shorts in denim and khaki, with frayed edges, or loosely rolled fabrics. Both these effects look absolutely terrible on me so I have had a devil of a time finding additional pairs.

    I agree with the other commenter that Old Navy has totally stepped up there game by providing basic cotton khaki shorts with flat fronts, normal flat hems, in several lengths at a very affordable price!

  6. Ann M.

    I was wondering where this post had gone! Glad it's back up, because I think it's a great one – absolutely love that you consider not just the body types that are usually featured in magazines and such, but also different ones. And yes, I realise that is part of what you're all about, but it's so great that it can't hurt to point it out again, right?

    As for shorts: I love shorts because they're, well, pants- only shorter. I love skirts and dresses, but don't like my thighs touching at all, so when it's too hot for tights under a skirt or dress, shorts are usually the way to go for me. I put on a pair this morning, but then the weather decided that it would like to give us some thunderstorm as opposed to sun today, so no shorts for me today.

  7. Rubiatonta

    I'm a city girl, so shorts don't make much of an appearance in my fashion rotation. I do have a couple of pair of longer (9") Bermuda shorts that I wear when the occasion calls for it. I've got quite heavy legs, so I prefer to keep the length on the longer side.

    One pair is black polished cotton, and bought from Talbots; the brownish-green canvas, bought from J. Jill before they turned into Back Order Hell. (I'm having an experience with them that's not entirely unlike the one you just had with your boots, except I haven't found anyone to make me happy yet. A three month plus wait for a pair of black linen pants? Oh, yeah, that's totally reasonable, especially in New England, where linen pant season is about three months long. But I digress… and froth a bit…)

    Thanks so much for the pointers on what to wear on my feets with the shorts — I've got a pair of black KorkEase that I am going to try, just to see how it looks.

  8. Anne

    Thank you Sal! And thanks for re-posting — I could see this in Google Reader, but couldn't comment yesterday.

    Since I wrote you, I invested in a pair of bermuda shorts that have a tab so you can roll them up if you wanted (although I've yet to do that), and they're working out alright.

    I never would've even thought about the shoe pairings, but I see what you mean about lengthening the leg with your shoe choice. I definitely prefer flip-flops all summer long, even though I know they aren't doing me any favors. Perhaps it's time to invest in a pair of wedges.

  9. Phoebe

    I'm not sure I agree with the assessment of that kind of long short as flattering. Even the images you've chosen kind of bear out what I often think– that really long shorts like that make legs look more masculine and stumpy. There's got to be a midground between that and short-shorts that doesn't have such a… coarsen-ing effect.

  10. Elizabeth

    I live in Southern California so shorts are a weekend/ after work staple spring, summer, and fall. I like 3" shorts because I have muscular legs and any longer hits at the widest part of my thigh. I have become aware that most women my age, 48, stick to capris ( yuck!) or skirts, but I feel best in shorts. I do like the shorts with heels look but my teenage daughter thinks this is inappropriate for my age so I have resisted. i like the idea of wedges with some longer shorts.

  11. Future Lint

    I'm a big fan of shorts! The only major thing I've discovered about them is that they tend to be more flattering if I go up a size than what I usually wear in that particular brand of pants. I don't know, there is just nothing flattering about a too-tight short (be it at the stomach, hips, thighs, etc)… So bring a few sizes of the same pair in and be honest about what is flattering, not the size on the tag!

  12. Jenniferocious

    Ugh, I never wear shorts. The two pair I have are bermuda-ish, though neither are truly quite there. One pair is cuffed and sits a couple inches above the knee, the other are fairly fitted and hit right at the knee, with a little opening at the bottom of the outer leg seams. Both are dark wash denim, and the longer, narrower ones are my favorite.

    I generally live in skirts and dresses in the summer, and usually don't care if I'm a little too dressed up. I make the top half of my outfit, and my footwear, more casual to compensate. Skirts are just so much easier to fit! I have issues with pants & jeans… if they fit me in the thighs, then they're too big in the waist, and I have to belt them like crazy. Sometimes I just don't want to wear a belt, ya know?

    I never ever wear shorts (or pretty much anything, for that matter) more than a couple inches above the knee. My thighs are one of my absolute biggest hangups about myself, as I feel that they are disproportionally large when compared to my lower legs, and I have stretch marks on my inner thighs from when I was heavier toward the end of high school. I'm working on trying to get over this, but for now I'm still not able to suck it up and flaunt them in public.

  13. Lorena

    You are such a great read SAL !
    You got the best articles !
    I loved your post.
    I love shorts but I almost never wear them.
    Found a LL Bean black straight front pair that fits well but my legs are totally out of shape.
    So, honestly speaking you can see cellulite here and there, so I just decided to wear them "close to home".
    I feel that bermudas make me look stumpy but it's either that or getting on that bike !

  14. LK

    Old Navy usually carries shorts in three lengths Really short, medium and burmuda (knee length). Its really nice to have the options. Their Burmuda shorts are somewhat narrow so they dont add extra bulk to the leg.

  15. Rosie

    Great post!

    A quick observation about the bermudas shown with different shoes: The gladiators actually hit above the ankle, covering it up, while the t-strap wedges hit just below the ankle and show the ankle bone. In addition to the height, this has a HUGE effect on the proportion.

  16. Vanessa

    I'm not really into shorts, but a lot of the pairs you picked are quite cute (I was a little more interested in trying to find those shoes from the GAP photos, though). I have to agree with Phoebe that a few of the combos definitely make these ladies' legs look a bit masculine: I genuinely thought the last photo (flip flops) was a dude when I took a quick look.

  17. Rachel

    shorts are a staple 9 months out of the year in FL. I wear them frequently on the weekends cuz sometimes you just don't feel like wearing a dress/skirt (that's my normal go to for any day of the week).

    NY&Co & LOFT carry multiple styles and inseams, but they are a little pricier. Target has a good selection of shorter shorts, but I totally agree that anything shorter than 3" is too short. I did wear them as a teenager though. 4" inseam is my preference, they're not too long and not too short. Anything longer makes me look very short and scrawny/chicken leg (yes, I will admit to that). I wore a lot of bermudas a few summers ago when I had some skin allergy issues, but they are not very flattering for petite, "I" body shapes. I like lightweight woven cotton materials best, but will wear denim.

    Another great, informative post Sal!

  18. lisa

    I like my shorts on the shorter side but never so short that when I bend over I risk overexposure. Details like dressier fabrications, cuffs, oversized buttons, a high waist, pleats, or vintage styling appeal to me more than casual options.

  19. Cynthia

    About the only shorts I have that I like are not really shorts, they're knee-pri length and cut skinny (or they were before I shrank a couple of sizes). Not bermudas, not capris. Athleta called them "knickers" which I was amused by. I do have, and wear, some hideous cargo shorts, but I don't consider them an element of my personal style. More an embarrassing weekend aberration.

  20. Julia

    I went through a no-shorts-ever phase in college and early grad school. But sometimes they just make sense. I like skirts in the summer, but I don't like my thighs rubbing together to give me a sore spot. Shorts are perfect to solve this problem. I like the Bermuda's that are just a few inches above the knee.

    I also have a pair of shorts with a 3.5 inch inseam, which I don't think are too short on me – there is plenty of room in the thigh. See them here:

    I wouldn't wear these to a work environment, but they're fine for wearing around town or around the house, (or to my grad school student offic) I think at least.

  21. WendyB

    Premature post-jaculation, eh? Don't worry, it happens to everyone. Really.

  22. pretty face

    I was just wondering why you were so anti the short shorts?

    I find on my body the shorter the short, the longer the leg looks and my thighs are definitely more toned than my calves would give the impression of, as I have naturally muscular calves.

    # Who likes short shorts? I like short shorts #

  23. K.Line

    I'm totally pro shorts. I prefer ones on the short side with a flat front. For me it's the stomach I try to de-emphasize.

  24. Erin

    Panties with a zip fly! That might be one of my favorite phrases of all time. And would make a cool punk band name.

  25. (Hard G) Gillian

    I'm going to have to agree with the few comments in favor of short-shorts. I live in Lancaster, Pa, and can barely bear the 80-100 degree temperature range we have in the summer. I prefer as little clothing as possible, and would prefer to run around in my swim suit, but unfortunately that's frowned upon past the age of 10. Being very thin and average height, shorts that hit between mid-thigh and mid-calf kind of make me look like I'm wearing my mom's clothes playing dress-up. I like my shorts to be short-short or capris, because they make my legs look the best. I'm also only 21 and think you should wear whatever you want while you're confident enough to do it! But there is definitely a time and a place, and I prefer neat, clean jean shorts with a cuffed bottom or other semi-tailored short shorts. Not to say I won't wear daisy dukes, but that's around the house.

    Here's some of my favorite short shorts. I'm curious what you think!

    Though I guess high-waisted short-shorts don't have that 3" inseam!

  26. Rosie Unknown

    I have no problem with short shorts in general (as long as they are situation appropriate), but I do have a problem with shorts on ME. I have no problem wearing ultra mini skirts, but the minute a pair of shorts hits me above the knee it starts looking crappy.

  27. Sal

    pretty face and (Hard G) Gillian: I couldn't really say what it is about short shorts that disagrees with me. I think it's just that I've never seen them on anyone and thought, "Those look great!" Gillian, your high-waisters are darling, but just not my taste. Sorry I can't be more articulate. Some things you just don't dig, ya know?

  28. Jesspgh

    I just found some shorts at Old Navy last week and I love them! If it wasn't so mild here, I'd be wearing them every day. But come next week when it gets hot again, I will.

    I am short and curvy so I used to avoid shorts but it got to be too impractical and limited, especially in summer. Here is my post with shorts on short and curvy me. 🙂

  29. DailyDivaDish

    I love that you discussed shoe choices and their importance in elongating the leg. It makes such a huge difference, as your photos clearly demonstrate. That's why wedges with a criss-cross strap are my favorite kind of shoe for summer. Great post!
    XO Piper

  30. (Hard G) Gillian

    Re your statement on short shorts: "Sorry I can't be more articulate. Some things you just don't dig, ya know?"

    But Sal! Being articulate, especially about clothes and proportions, is what you're known for!

    I can't remember if you've done a post on how modesty relates to figure flattery and body confidence before, but if you haven't, I'd love if you would!

    Modesty is almost never one of my priorities when getting dressed, and what I consider modest might be considered inappropriate to someone else. Meanwhile I see plenty of girls every day wearing outfits that I'd never leave my room in. Where do your opinions on modesty come from, how would you describe them, and how do they relate to your concerns of figure flattery and body confidence?

  31. Leona

    I generally dislike shorts, but have recently become interested in them as casual options for muggy days or impromptu trips to theme parks, where skirts just aren't all that practical. This post of yours came at the perfect time; I was just wondering about what length would suit me. Being one of those lithe teenagers, I could probably get away with wearing those miniscule 3-inchers; but, I can't help but think that they're a touch too immodest, even for around-the-house ventures. My view of modesty is somewhat lax (being purely based off of my own tastes; no religious influences or anything like that), but they're still important to me – and those teeny little shorts push the boundaries quite a tad.

    As such, I tend to prefer slim-fitting bermuda shorts; the wider-leg ones tend to adverse effects on my slenderfigure. I've been oogling a 5-inch pair from Lands' End ever since I saw them featured in their catalog, but I'm not *quite* convinced. Still, I love the outfit, and the shorter-but-not-too-short length should be flattering on me. I'll just have to try, I suppose. 😀

  32. Sal

    (Hard G) Gillian: Actually, I did describe my feelings a bit in the post.

    The shorts that I like least are both short and tight, or so short that you can see butt cheek hanging out the back. So perhaps the 3" inseam isn't a fair marker, but when I looked at vendor images of shorts that made me frown, most were listed as 3", which is why it ended up in the post. That measurement will look different on different women, depending on thigh length and overall leg length.

    I am a fairly modest dresser myself, but certainly don't hold anyone to my personal standards. However, as I mentioned in the post, shorts that are just shy of hotpants – which I have totally seen on women on my campus and around the Twin Cities – are essentially underwear masquerading as regular clothing. Why don't I like that? If the shorts were made of jersey instead of denim, they would be actual underwear and there wouldn't be any argument for wearing them in public at all.

    I don't think I should be able to see someone's butt cheeks unless I actually WANT to. I don't think I should see someone's bikini line if we're not at the beach or the pool. If people started wearing tops so short that I could see the the bottoms of their boobs, I wouldn't like that either. Maybe it's stodgy, but I think covering your bikini line and butt cheeks is the respectful thing to do when you're out and about. And short shorts often fail to do that.

    I have a post on modesty coming up in a few weeks.

  33. Lady

    this is an interesting post for me. I have a wierd history with shorts. basically, my mother wouldnt allow me to wear them to school as a child and teenager. so OF COURSE it was the only thing i wanted to wear with a burning passion.

    i've never felt i got a clear answer why (im now 28). to some degree she seemed to be concerned with the fact that i had a womanly figure when i was still quite young. but i don't understand what the rational was after I got over the age of 16. I believe in my senior year of high school i had one pair that I daringly wore and she possibly may have been too worn out to fight me over it.

    now you'd think i'd be wearing them all the hot summer long as an adult, but i don't. frankly, many lengths don't flatter me. i'm officially plus sized now at a size 18-20. I have toned calves but i carry lotsa extra poundage in the thigh area and it doesnt look its best in most shorts. The compromise is a pair of black trouser bermudas I scored from Lane Bryant a few years ago that come to my knee. they fit and flatter perfectly. If i could find this cut in other colors I would consider them but haven't really looked hard.

    i do plan to break them out in the office this summer on very hot days. I will wear them with kitten heeled sandals or wedges as I agree with the leg stumpification that some shoes create. I'm 5'8 and not immune.

  34. KL

    Interesting to hear your argument against short shorts. I do think that 3″ inseams look very different on petite women than on the models. I’m young enough to have worn some extremely short shorts, but have now settled on 3″ as the ideal length. I feel like longer shorts cut off my leg and make me even shorter than 5’2″; if I want more coverage, I’ll wear capris or a skirt. I’d I’m wearing shorts, I don’t want to bother with heels.

    On the other hand, I’m not comfortable in skirts shorter than a hands width above my knee, and I do judge people silently for a certain length of mini.