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Footwear 5 min read

Matching Shoes With the Right Outfit: A Pairing Guide

Which shoes work with which outfits, from flats and ballerinas to pumps, wedges, stilettos and boots, with the pairings to avoid and why.

On this page

Most outfits fail at the feet. The garment is right, the shoe is right on its own, and together they cut the leg in the wrong place or throw the proportions out.

This guide works through each shoe type, what it pairs with, and what to avoid.

Flat shoes

Flats, including ballet flats and skimmers, work with skinny jeans, casuals and semi-casuals, and with short skirts and minis. Skimpy flats also suit long dressy skirts. Pointed-toe flats are a good option within the category.

What to watch

Pointed toes make the foot look longer than it is. Flats suit tall, lean figures best, because unlike heels they add no illusion of height.

If you want height from a flat, pair it with a mini skirt. Maximum exposed leg is what makes you appear taller, and the shoe itself does not have to do the work.

Flat shoes paired with a casual outfit
Flats work best where the leg is already long or largely exposed

Ballet flats

Ballet flats suit tall women particularly well. Pair them with capris and cropped trousers that are neither too wide nor too long, and with shorts and mini skirts.

Avoid

  • Long skirts. Ballet flats and skimmers are not a good match, and on a shorter figure the combination makes you appear shorter still.
  • Heavy or short legs. The shape does not flatter either.

By material

  • Canvas ballet flats suit casual outfits, and pair well with cotton or denim shorts and skirts.
  • Leather ballet flats and skimmers also read as casual, and work with jeans and shorts.

Embellished ballerina flats

Made from luxurious materials such as satin, with intricate detailing in pearls and stones. The embellishment lifts them well past casual, so they work with elegant, ethnic and dressy outfits as well as with casuals and formals.

Ballerina flats generally

Pair with capris, leggings, shorts and short skirts. Petite women should choose a shorter skirt, which exposes more leg and creates height the shoe cannot.

Avoid

  • Pleated or overlong trousers.
  • Narrow-legged trousers, which make the legs look shorter and the hips wider.
  • Relying on them for height. Ballerina flats have no heel at all.

Flat thongs

Best with short shorts.

Pumps

  • Skinny jeans with slightly pointed pumps.
  • Mini skirts with high-heeled pumps.
  • Cropped trousers with peep-toe pumps.

Sneakers

Sneakers work with short skirts and denim. Streamlined shapes read as more classic than bulky ones. Canvas sneakers are firmly casual.

High heels

High-heeled sandals pair with skinny jeans, and with dressy skirts including long flared shapes. They elongate the leg, which is the reason to reach for them.

Wedges and platforms

Wedges with a substantial heel work with short skirts, and cropped trousers pair well with wedge sandals. Minis and wedges are a reliable combination, and closed-toe wedges suit casuals and short skirts.

How to choose one

Wedges are bulky by construction, so the design has to compensate. Choose styles with straps or slides that show as much skin as possible, which keeps the shoe from reading as a solid block. Espadrille, strappy and woven open-toed styles all do this well.

Platform heels are a good option if you want more substance underfoot. For a leaner line, choose the less bulky versions.

Stilettos

Stilettos work with long jackets and skinny jeans, and with mini and pencil skirts.

Kitten heels

Pair with cropped trousers and short skirts, and with dressier pieces such as long flared skirts. Kitten heels are the most versatile heel in this list.

Boots

Boots work with skinny jeans, and ankle boots and heeled boots both pair well with denim.

Avoid boots that are both short and bulky, which is the least flattering combination available.

Tall boots

  • Wide-cut cropped trousers with knee-high boots.
  • Long skirts, which are a natural pairing.
  • Pencil skirts with heeled, close-fitting boots.

One technique worth knowing: choose boots tall enough to reach the hemline of the skirt. Closing that gap makes the leg read as a single unbroken line and produces the longest, leanest effect available from footwear.

Ankle boots

Avoid with cropped trousers, tights, shorts, capris and mid-length skirts. All of them end near where the boot ends, creating two horizontal breaks close together.

Quick reference

Outfit Works with
Skinny jeans Flats, pumps, high heels, stilettos, boots
Mini skirt Flats, high-heeled pumps, wedges, stilettos
Cropped trousers Ballet flats, peep-toe pumps, wedges, kitten heels, tall boots
Long flared skirt High heels, kitten heels, tall boots, skimpy flats
Pencil skirt Stilettos, close-fitting heeled boots
Shorts Flat thongs, ballet flats, ballerinas

Frequently asked questions

What shoes make legs look longer?

High heels, and tall boots that reach the hemline of the skirt so the leg reads as one unbroken line.

Why avoid ankle boots with cropped trousers?

Both end near the same point, creating two horizontal breaks close together and shortening the leg.

Can short women wear flats?

Yes, paired with a mini or short skirt. The exposed leg creates the height the shoe does not.

How do I stop wedges looking bulky?

Choose strappy, open or woven designs that show skin. A solid closed wedge reads as a block.

See also footwear for women and how to appear taller.

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