How Shoes and Shorts Interact

how to pick shoes to wear with shorts

But before I dig into how shorts and shoes play off one another and affect body proportions, one quick note:

Yes, you can wear shorts. I don’t care how old you are or how much you weigh or what your legs look like. If it’s hot and you want to, you can throw on a pair of shorts and wear them to your heart’s content. Whoever said that certain body types and age groups should avoid shorts is a Clothing Tyrant and should be 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.

There, now that THAT’S settled, let’s talk about the shoe-short connection.

Long shorts with high vamp shoes

Image courtesy Gap

Although short shorts seem to be the prevalent available style, there are longer alternatives. J. Crew, Talbots, and Land’s End all offer shorts in inseam lengths from 3″ (J.Crew only) to 13″. I was also pleased to find several longer lengths mixed in among the teensy offerings at the Gap, so perhaps a few mall-based faves are diversifying their offerings.

Longer shorts such as Bermudas are fantastic in the coverage department, and if that’s your objective, then by all means go long. But if you are concerned about how longer shorts may interact with your figure, consider this: A SKIRT that hits at the knee allows the observing eye to imagine thigh shape relatively freely. A pair of loose shorts that hits at the knee may trick the eye into believing your thigh fills most of the pantleg. (Even if it doesn’t.) If showing your true leg shape is a figure-flattery priority for you, revealing some knee and a wee bit of thigh above the kneecap may help.

And then there are your shoes to consider. In the photo above, the long-ish shorts have been paired with dark sandals that hit at the ankle bone. Even though they are fairly tall wedges, their high vamp alters the perceived leg line. The leg is cut off at the ankle by the shoe creating a shortened leg. If a long leg line is a figure-flattery priority for you, high vamp shoes may not be the best choice.

Image courtesy Nordstrom

These high-vamp sandals are a bit more airy due to their thin strappy nature – the break they create at the ankle is a bit less severe – but they’re also flat. The dark, high-vamp wedges above mitigate their own shortening properties through their height. High-vamp flat sandals paired with long length shorts shorten the leg line even further.

Long shorts with low-vamp shoes

Image courtesy Nordstrom

The lower the vamp, the longer the leg line, and in sandal world it’s tough to get lower than flip flops. Here, a pair of shorts that’s approximately the same length as the olive green ones above creates a longer leg line when paired with these low-vamp sandals. They’re flat, but the perceived line is still far longer!

Image courtesy Nordstrom

These flats hit further up on the foot than the flip flops, but still work beautifully with longer length shorts. Since the eye goes from short hem to shoe vamp, any shoe style that exposes the top of the foot will help bring that leg line down a bit lower.

Short shorts with high vamp shoes

Image courtesy Gap

These shorts hit much higher on the leg than the previous pairs, so although the high-vamp oxfords do cut off the leg line fairly high up, it doesn’t have a huge impact. Enough leg is exposed that an otherwise leg-shortening shoe works quite well.

Image courtesy Macy’s

High-vamp shoes featuring heels, platforms, or wedges also balance nicely with shorter length shorts. The added height of the shoe balances the potential shortening of the high vamp.

Short shorts with low vamp shoes

Image courtesy Macy’s

If you really want legs that go on for miles, shorter length shorts worn with low-vamp shoes should do the trick. (Here, the tan shorts are fairly close to the model’s skin tone, which adds to the lengthening. More on that in a bit.)

Image courtesy Gap

Once again, heels, wedges, and platforms will do even more to elongate those gams. At a certain point, though, you may feel like you’ve swung a bit too far in the long-leg direction. Micro-mini shorts paired with towering platforms can make a woman look like she is 85% leg. Many adore a super long-legged look, but others may prefer a more balanced silhouette. Elongate to your heart’s content, but be aware that you can create a different kind of imbalance in your figure if you over-elongate.

Any shorts with any vamp nude shoes

Images via Gap (left) and Nordstrom (right)

If this whole vamp thing just makes you think of bloodsucking night creatures and you can’t be fussed, consider choosing a sandal or shoe that approximates your skin tone. As you can see above, high vamp sandals in nude or near-nude shades look lovely with longer shorts.

Images via Nordstrom (left) and Gap (right)

And they work equally well with shorter styles! If you go nude, vamp and heel height both have less impact. Flat, heeled, pumps, gladiators, they all make for long-looking legs if they’re in a shade that blends with your legs and feet.

Now, as in all things figure-flattery, YOU get to decide if elongated legs are a priority. None of my figure flattery advice posts should be considered gospel, including this one, and I fully expect you to read them with a grain of salt. Style “rules” are merely guidelines, no matter who is dispensing them. I trust you to use your judgment, take what applies to you, discard the rest, and assume positive intent.

Personally, I love the look of boots with shorts, and boots hit higher on the leg than any of the shoes shown here! But when I’m doing shorts and sandals, I do pay attention to how the short length and shoe design interact.

Related posts:

*On the flip side, if you don’t enjoy wearing shorts, don’t feel obliged to wear them. You get to decide what feels and looks best on your own figure.

**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 2012-07-19 06:13:56.

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26 Responses to “How Shoes and Shorts Interact”

  1. Stephanie

    Oh oh! I love your post 😀 I am going to have to come back and read this in more detail! Thanks, Sally!

  2. Patti @ NotDeadYet Style

    So many good ideas and cute images here. I don’t usually like shorts for me, although I do own a pair just like the GAP knee-length denims you’re showing. I see that the nude shoes really extend the leg – must try!

  3. Sonja

    I love long shorts + low-vamped heels. Make my litte stumpy legs look really long and sexy. Nice tipps, I really should try to find a pair of shoes similar to colour of my skin …

  4. Cynthia

    My favorite shorts style is the skinny bermudas that end just at the knee. I don’t really monitor shoe-short balance at all, because I’m constrained in the shoe styles I’m willing to wear.

  5. Rachel W.

    This is an instant classic Already Pretty post– thank you so much for writing it, Sal! I’m very much a shorts novice: I just bought my first pairs after years of hating the garments, and I’m still feeling out how to best deploy ’em. This post directly answers some questions I didn’t even know I had!

  6. Molly

    I hate shorts! I’m a size 4 or 6 in skirts and dresses, but when I wear pants or shorts, my size jumps up like crazy. Full thighs! I have been living in skirts, which I love, but sometimes I need shorts with pockets that actually hold stuff, for riding roller coasters and hiking. Of course, cargo pockets on full thighs are never going to look right. What to do? Get used to flashing people on coasters? Time to go sew some cargo pockets on a skirt!

    • Roxane

      Molly –

      I’m another who gave up shorts because skirts are just so much better for me and my thighs. My solution to the problem you describe is skorts. No, not the lame kind they used to make that show the shorts in the back, but cute skirts with sewn-in undershorts. The outdoor-wear brands even make them in light-weight, hard-to-wrinkle fabrics for hiking–with pockets! Athleta has lots of styles, though I’m sure REI and other brands have them too. I got this pair and love them.

      I’m a size 4/6, with largish thighs. The shorts do ride up a bit, but not enough that it’s uncomfortable. And they have a hidden drawstring to help fit the waist.

    • Sonja

      Molly, if you just hate shorts, I recommend you wear biker shorts or hot pants underneath your skirts when there’s danger of flashing.
      But i suppose this will only work when it’s not too hot where you live.
      And there might even be solutions for the pockets-situation: I suggest you look for those flash-coloured travel purses that you can wear underneath your clothes, there are different types, ones that are like a belt or a harness, and they might be big enough for the things you want to have at hand. Again, only a good idea if it`s not too hot and your clothes are not see-through/ too thin/ really tight.
      If you are not worried about adding a bit of volume around your hip, watch out for Skirts and dresses with pockets or ask a tailor to add some, that should not be too difficult. I suppose you could even add a zipper or velcro, so that nothing falls out.
      Just a couple of ideas, I hope it helps!

  7. Anne

    Great post. I just might print it up and hang it with my shorts. It took me a few years to learn that I actually look better in shorter shorts. I have never found the low-rise snug-legged Bermuda shorts to be either comfy or flattering on me. There are places where short shorts just aren’t really appropriate so it is nice to have all these options laid out. The mercury is going back up to the high 90’s this weekend so this post couldn’t come at a better time.

  8. Mia

    Shorts! I recently bought my first pair of short shorts in years:

    I thought I would be nervous about wearing them, but discovering that I wasn’t has opened things up for me! I didn’t know the the terminology before, but I have been aware that, especially having larger ankles and calves, higher-vamped shoes (and wearing socks with shoes) tends to cut my legs off at a weird place, which some days I care about more than others. Now, the next step is to figure out how to wear wedges/heels + intentional socks + short shorts while feeling comfortable temperature-wise…

  9. Anneesha

    This is an excellent post! And so good to see photos of non-stick thin models. Today I’m coincidentally wearing white knee-length bermudas, (thrifted Falconnable!) with nude high-vamp chunky heeled mules and it’s working great!

  10. LG

    Thank you for this post! Prior to it, I didn’t understand why certain shoes of mine didn’t go with certain shorts, but now I think I know why… :0)

  11. bubu

    terrific post, thanks! this is also reminding me of the nude-sandal-shaped hole in my wardrobe, which i’ve been meaning to fill all summer. now is probalby the time, sales are everywhere.

  12. Amy

    The whole anti-shorts movement was from OPRAH!!! True story.

  13. Megan Mae

    This is an interesting post. Maybe it’s because I’m thin and look visually taller than I am, but I really prefer ankle height shoes. Knee high boots tend to make me feel ill proportioned, low vamped shoes make me feel “naked”. I own exactly one pair of actual shorts because of the whole naked-leg feeling.

    Liking the ankle-boot/shoe tends to be the opposite of what most people aim for when dressing, and I often do a double take when someone complains about “looking short” – I tend to like the effect of petite curvy legs. Maybe it’s because I have very skinny ones and wish I had more curve.

    • Audi

      I was just stopping by with a similar comment! I think any length of short with a high vamp looks great regardless of leg length or shape, and to my eye it looks more modest somehow. I feel very, very exposed in a pair of short shorts with a low vamp shoe, unless it’s a very casual outfit and the shoes are flat sandals or flip flops. Sal, I love the tips you present here, and the photos perfectly illustrate your points.

  14. WendyB

    I definitely think when it’s over 100 degrees, anyone can wear shorts. I don’t care what their legs are like!

  15. Emily

    Sally, this post is a great reference for balancing shorts and shoes, but what I really wanted to thank you for is your use of photos that feature women of different sizes, as well as your continued message of body acceptance. I’ve been going through a really rough time lately with my body image and self worth, and your site has really been a balm to me and my confidence. Thank you so, so much.

    • Sal

      Oh Emily, thank you for your kind words. Very, very glad to help, and hope you find some body image solace in your own time.

  16. Aging fashionista

    Very helpful. I love skirts and dresses in summer but shorts are much more practical for things like biking,canoeing and sometimes picnics. As are flats, and the combo tends to exaberate my short and stocky ness, but you have identified some more flattering options that I already have in my closet! Thanks!

  17. shebolt

    Thank you for supporting the position that all women can (and should) wear shorts! I get so frustrated when I hear women say they won’t wear them because of their age or their size.

    I’m 41 and athletic, and have never shied away from shorts. I have good legs but odd knees, and I don’t care that my knees aren’t great. This year, I actually bought some that are shorter than my cycling shorts. Yes, my tan line shows. But I earned it so I’m going to show it!

  18. Kim

    This is my first time reading your blog, and this post was absolutely fantastic. I have ONE pair of shorts that fit me correctly, and they are from a cut up pair of great jeans! I really want to buy more shorts, however with my apple figure I find that if the shorts fit my waist properly, they are too baggy in bottom OR I feel like they’re trying to take residence up there! Because of this, shorts shopping is one of the most depressing experiences for me.

    I also have trim, athletic, yet short legs, so I’m not sure if I can really get away with bermuda length, even with a shorter vamped shoe. I’m also quite top-heavy, so I feel like shorts make me look like an upside-down triangle! I feel like I need my bottom half to be fuller (please don’t hate me for saying that) to balance out my top. Perhaps if I go for a mid-thigh short that’s looser and maybe cuffed? Thoughts?

    Thanks for this fantastic blog!

    • Sal

      Welcome, Kim! And I’d never hate you for wanting to create balance in your own figure. Honest. Yes, I think you’ve got the right idea – a mid-thigh length that flares a bit at the hem should do the trick. Cuffs are also a good idea. Hope you find a pair you love!