What Shoes to Wear

Betsey Johnson

Betsey Johnson in a maxi length skirt and wedges

No matter how fabulous your shoes or your clothing – if they aren’t well-paired, an outfit can be a total flop. Below are some tips for the best shoes to pair with the most commonly-worn bottoms:

Shoes to Pair With Capris and Cropped Pants

Ballet flats with a slightly pointed toe will help elongate the leg because capris and cropped pants tend to cut the leg line off in the middle of the calf. A black ballet flat always works well, but recent iterations like capped-toe flats or even embellished smoking slipper styles will work well because of their focus on the toe.

Espadrilles are flat shoes with a slightly pointed toe that are made of canvas or cotton fabric, and have a flexible sole made of rope (or rubber molded to look like rope). It’s a great casual shoe choice and perfect for the summer.

Wedges add some height and go well with the more casual nature of the cropped pant. It is best to stay away from stiletto heels as they can be too formal and dressy for capri-style pants.

The Perfect Shoes for Skirts

Maxi Skirts

Sandals, especially embellished ones, work well with the casual nature of maxi skirts. Flat sandals are best for maxi skirts in keeping with the casualness of maxis – look for stylistic elements that add interest, including gemstones, gladiator-style lace ups, or even  simple strappy sandals in a bright color.

Wedges also work well with maxi skirts (and hi-low skirts!) – pick ones with a manageable heel height. Look for peep-toe wedges or nautical details for a fun summer style.

Knee length skirts

ballet flats

Wear ballet flats with a casual knee length skirt

Leather heels with pointed, almond-shaped, or even round toes will work well with knee-length pencil skirts. Heels lengthen the leg and generally is the best option when wearing a tighter-fitting pencil skirt. For office appropriateness, the heel should be no higher than 3”.

Ballet flats will be perfect for more casual knee-length skirts, like those with knife pleats or box pleats. They come in a million colors and embellishments – you can pick something more embellished if your skirt is plain, but a basic ballet flat with a bow goes with everything.

Footwear for Jeans

Slouchy Boyfriend Style Denim

Sneakers and casual slip-on styles are perfect for slouchy jeans – think shoes in the style of Ked’s and Vans. A heeled alternative is the sneaker shoe with a hidden platform, which can be especially suitable for shorter girls.

sneakers and jeans

Canvas sneakers with Miss Me boyfriend style jeans

Heeled sandals add some glam contrast to casual boyfriend jeans. Stick with edgier designs, like gladiator-style sandals, lace-up styles, or even those embellished with studs as daintier shoes will make the look too unbalanced.

Bootcut and Straight Cut Jeans

Chunkier heels give your bottom a little bit of weight, especially considering the flared bottom of bootcut jeans. Wedges and shoes with a more substantial heel (no stilettos!) add balance to the silhouette. Look for retro-style shoes and simple wedges.

Heeled ankle booties work well for the colder seasons. These should peek out from under your jean, so consider an almond toe for a more slimming effect.

Skinny jeans

Ballet flats go well with skinny jeans, especially jeans that are ankle-length or have some embellishment around the ankle (for example, zips or cuffs). Think Audrey Hepburn as the quintessential model for this look.

Pointed-toe heels generally streamline the entire look. Having a pointed heel continues the straight leg line skinny jeans create and looks extremely sophisticated.

Tall boots are also a perfect fit for the colder months. Skinny jeans are perfect for boots because they tuck in easily without excess fabric. A dark brown with gold accents never fails with blue denim.

Things to Remember When Choosing Shoes

Your shoes should reflect the style of the clothes you’re wearing. If your clothes are casual, stick to casual shoes (flats and those made of canvas are usually more casual than leather shoes and footwear with embellishments).

Consider the occasion! If you’re attending a wedding on the beach, then wearing a pair of strappy stilettos would not be the best option. In the same vein, if you’re going to be walking a lot, then perhaps flats or sneakers would be most appropriate.

Lastly, have fun with it! The above are suggested guidelines, not strict rules. The key to great style is being comfortable in what you’re wearing.


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