What to Wear: The Best Shoes for Women's Shorts

of 07

What to Wear: The Best Shoes for Women's Shorts


Of course, choosing the right shoes for your favorite denim cut-off shorts is pretty easy: just walk to your closet, and grab the first pair of flip-flops or sandals that you find.

But there are so many different styles in women's shorts, and so many different shoes to wear with them, that the combinations are endless -- naturally, as with most things in life, some choices are far better than others.

This pictorial guide will walk you through several of the most popular women's shorts styles and suggest some of the best footwear options for each.

Pictured Above:

  1. Sanctuary 'Peace' Shorts (Image: Zappos.com)
  2. Free People Longer Cargo Shorts (Image: Piperlime)
  3. Vince Side Buckle Bermuda Shorts( Image: ShopBop.com)
  4. Fade-triotic Holiday Ombre Jean Shorts ( Image: LuLus.com)
of 07

The Best Shoes for Women's Short Shorts


While the idea of wearing short shorts scares the living daylights out of most women, there are those among us who actually can pull them off -- and love doing so.

For those who have been blessed with a certain body type, or enough confidence to dress however they please, I offer the following suggestions.

Women's Shoe Styles for Short Shorts

  • heeled, wide- or ankle-strap sandals
  • wedge sandals
  • embellished sandals
  • flat, dress sandals
  • cute and simple sneakers
  • espadrilles - flats or heels
  • simple pumps or ballet flats

Pictured Above:

  1. Joie 'Merci' Shorts​ (​Image: Zappos.com)
  2. Sanctuary 'Liberty' Chino Shorts (Image: Nordstrom.com)
  3. Scallop Poll Scalloped Coral Shorts​ (​Image: LuLus.com)
  4. BDG 'Erin High-Rise' Denim Shorts​ (Image: UrbanOutfitters.com)
of 07

The Shoes for Women's Mid-Length Shorts


A pair of mid-length shorts may not seem like the most dynamic item in your wardrobe, but they have a lot going for them. They cover some of the more problematic areas for a lot of women while exposing some of their better bits.

Another big bonus to women's mid-length shorts is that they can handle a wider variety of shoe styles than shorter or longer shorts can. In fact, you can successfully pair nearly any style of women's shoes with shorts that hit in the mid-thigh area.

Shoe Options for Mid-Length Shorts

To choose the best shoes for your particular mid-length shorts, let the following factors guide you: the rest of your outfit; your body type; and the time and nature of the occasion.

For a casual -- but still clean and polished -- look, try pairing your mid-length shorts with:

  • boat shoes
  • simple, streamlined sneakers
  • simple thong or slide sandals
  • mid-heeled pumps with open- or closed-toes
  • low- to mid-height wedge espadrilles

For a fun and carefree casual look, you can pair any of the following women's shoe styles with mid-length shorts:

  • flat, embellished sandals
  • chunky, high heeled sandals
  • cute, trendy flip-flops
  • wedge-heeled sneakers
  • cute, old-school sneakers in fun colors or prints

And, for a classic, casual-but-chic look, try the following shoes with your mid-length shorts:

  • simple, classic ballerina flats
  • dressy flat sandals
  • espadrilles
  • simple, mid- or low-heeled wedge sandals

Pictured Above

  1. Sanctuary 'Peace' Shorts (Image: Zappos.com)
  2. Free People Longer Cargo Shorts (Image: Piperlime)
  3. Hurley 'Lowrider' 7" Bermuda Shorts (Image: Zappos.com)
  4. Vince Relaxed Shorts (Image: Nordstrom.com)
of 07

The Best Shoes for Women's Long Shorts


Because they cover the thighs -- which a lot of women consider to be a "problem area" -- longer shorts are the first warm-weather choice for a lot of women.

The thing is, if you pair knee-length or long shorts with the wrong shoes, you might actually create another problem for yourself: the illusion of short, bulky calves.

So, what are the right shoes for long shorts?

Well, assuming you want your legs to look longer and slimmer, you need to do something that will lengthen the appearance of the leg that is showing. There are two ways of doing this: A) you can choose shoes with higher heels, or B) you can select flat shoes or sandals that expose a lot of your feet.

Those two options may sound scary to a lot of you, so let me ease your concerns by saying that you don't need to go super-high, or ultra-skimpy. For example, if stilettos scare you, you can choose chunky, wedge or mid-height heels; if you hate the idea of skimpy, flat sandals, you could opt for pumps with a low-cut vamp that won't expose any of your toes or the heels of your feet.

In general, if you want to wear longer shorts without making your calves look bulkier, you just want to avoid really heavy, overwhelming footwear, like puffy tennis shoes; ankle boots; or flat oxfords.

In contrast, if you feel that your legs already look too long and/or thin, then opt for shoes that offer a bit more coverage, and avoid wearing longer shorts with really high and skinny heels.

The Best Shoes for Long Shorts

With those tips in mind, here are a few of the most generally-flattering shoe choices for longer styles of women's shorts:

  • flat, skimpy thong sandals
  • flat slide sandals
  • wedge heeled pumps with open toes
  • wedge heeled sandals
  • flat, low or high heel pumps with open-toes
  • pumps or flats that are close to your skin tone

Pictured Above:

  1. Christopher Blue 'Liberty' Bermuda Island Twill Shorts​ (Image: Zappos.com)
  2. Vince Side Buckle Bermuda Shorts​​ (​Image: ShopBop.com)
  3. NYDJ 'Teresa' Walking Shorts​​​ (Image: Zappos.com)
  4. KUT from the Kloth Denim Bermuda Shorts​​ ​(Image: Nordstrom.com)
of 07

The Best Shoes for Women's Bermuda Shorts


A bit more forgiving than many women's shorts styles, Bermuda shorts tend to fall between the mid-thigh and the upper knee. They can be loose or form-fitting, but they're more tailored than baggy cargo shorts and they have nice, clean lines that make them a great match for some the same footwear you'd wear with business-casual pants or skirts.

Since they are on the longer side of the shorts spectrum, mid- to higher heels and delicate flat sandals tend to be the most flattering choices for most women; whereas bulkier flats, like sneakers and wide-strapped sandals, will make your legs appear shorter and heavier.

Some of the Best Shoe Styles for Women's Bermuda Shorts

  • simple, classically-styled pumps
  • delicate thongs, or other flat, thin-strapped sandals
  • open-toed flats
  • higher-heeled sandals
  • wedge pumps or sandals

Pictured Above:

  1. James Jeans White Bermuda Shorts​ (​Image: BarneysWarehouse.com)
  2. Dockers Misses 'Double Coin Pocket Bermuda'​​ ​(Image: Zappos.com)
  3. KUT from the Kloth Wide Hem Bermuda Short​ ​(Image: Zappos.com)
  4. Jag Jeans 'Louie' Pull-On Bermuda​ (​Image: Zappos.com)
of 07

What to Wear: The Best Shoes for Women's Cut-Off Shorts


Because they're so casual and fun, denim cut-off shorts are one of the easiest styles of women's shorts to accessorize. And while you could really pair almost any shoes with cut-offs, there are a few options that are better than others.

The main goals are to A) enhance their casual nature without looking sloppy or unkempt and B) to choose the most flattering style for the length of your shorts and your body type.

Since your cut-offs can be as long or as short as you want, and there are too many body types to account for in one article, we'll list a few of the most generally-flattering shoe styles for cut-offs, and suggest that you check out the following articles for tips on choosing the best options for the length of your shorts.

The Best Shoes for Denim Cut-Off Shorts

  • flat and delicate, embellished sandals
  • cute, slim sneakers -- think old-school simplicity
  • wedge sandals
  • flip-flops (wedges or flats)
  • higher-heeled sandals with wider straps

Pictured Above:

  1. Free People 'Dolphin Hem Cutoff Shorts' ( Image: ShopBop.com)
  2. Blank NYC 'The Solid Gold Cut-Offs' in Urban Cave Girl ( Image: Zappos.com)
  3. Fade-triotic Holiday Ombre Jean Shorts ( Image: LuLus.com)
  4. Billabong 'Laneway' Shorts (Image: Zappos.com)
of 07

What to Wear: The Best Shoes for Women's Athletic Shorts

Joggers running on bridge
Kevin Kozick/Getty Images

While some girls and women need to wear athletic shorts for certain activities or sports, others just like wearing running, jogging, or other athletic-styled shorts because of the cute, casual, and sporty look they have. Whatever reason you have for wearing them, you'll definitely want to choose the right shoes for the best look.

Of course, if you're required to wear shorts for a specific sport, then you probably also need a specific kind of shoes -- in which case you're already sorted.

But, if you're just wearing sporty shorts just because you like them, then your choices are simple -- because there are only a few women's shoe styles that will really work well with them.

For example, it's probably fairly obvious to most of you that heels of any kind really aren't the best match for athletic-styled shorts -- not that it's never been done (everything has), it's just usually not a great look. The same can be said for boots, dress shoes, dressy sandals, and dressy flats.

So, what should you wear with your basic sporty shorts? Sneakers, casual flat sandals, and flip-flops are all good matches -- basically, you want something as casual and cute as the athletic shorts themselves.