The Best Shoe to Pair with Every Type of Bottom

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STYLECASTER | Pants & Shoe Pairing Guide
Photo: Getty Images

Maybe it’s just us—do you ever start planning your outfit from the bottom up? Shoes are probably one of the most important components of an ensemble, but how do you pick the correct bottom to style with them? Have you ever wondered, “Is it OK to have a two-inch gap between the bottom of my jeans and my boots?” or “What kind of shoes go best with culottes?” If you have asked yourself these questions, silently or aloud, you’re not alone. But we’re here with answers.

Below, we demystify the art of below-the-knee pairings by breaking down a few of the chicest combos.

The Skinny or Tapered Pant

The popular skinny jean can be paired with almost any type of shoe, but there are some ground rules. Skinny or tapered bottoms should always hit at the ankle or at the top of the shoe. If you’re wearing an ankle boot, you can cuff your jeans; or pair a flat with your tapered dress pants. Another option if you’re trying to elongate the leg even more is to pair the pant with a pointed-toe pump. The extra skin and length of the shoe will instantly add a couple inches of length to your leg.

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MORE: 30 Things Every Woman Should Own by Age 30

The Flared Pant

There are three shoe rules—or options—when you’re wearing flared pants. The first is to have your shoes not be seen at all. If you’re wearing a big enough flare, the shoe should be hidden and the pant will graze the ground. The next option is to add a little structure with a pointy-toe pump. Last, you can opt to keep things casual with a flat or sandal.

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The Straight-Leg Pant

Straight-leg denim has become increasingly popular in the past year, and we’re loving the mix of sneakers, flats, and slides for this style. It’s casual and effortless and will keep the focus on the straight leg. Below, check out a few low-key ways to style the look.

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The Crop-Flare Pant

These pants can be awkward when styling, so look for shoes that will help add some height, or even boots that will allow for a couple of inches of overlap.

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The Mini

The miniskirt or dress is all about legs for days. Play up yours with a pump or a shoe that doesn’t “cut off” your foot or leg. That means avoiding chunky ankle or calf boots and looking for shoes that keep the attention on the mini. A pump or over-the-knee boots are a great option for keeping your legs looking long.

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The Pencil Skirt

The best shoe to pair with a pencil skirt is a pointed-toe pump or strappy heel. This will elongate the legs since the skirt is hitting around your knee. Another trick to keeping your legs looking great is to style your skirt with a neutral or nude heel.

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MORE: How to Style a Dress and Stay Warm During Winter

The Midi

Look for shoes that add a little height! Platforms, open-toe heels, and mules are a great way to give you a few extra inches and again avoid the dreaded cut-off feet look.

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