The Correct Type Of Shoe To Wear With Every Style Of Pants

If I had a dollar for every time someone asked me what shoe to wear with each of their pants, I’d be Kylie Jenner-rich. Okay, disclaimer, I’m a store manager so it’s a little less odd than you think it is. Nonetheless, this is a valid dilemma that many women all across our great nation face on a daily basis. So, I’m here to do my civic duty of helping all of you have an easier time getting dressed in the morning. Here’s a definitive guide to exactly what style of shoe you should wear based on different styles of pants.

1. Skinny & Tapered

A skinny or tapered pant needs a slim refined shoe to further elongate the leg, keeping the look chic and polished. A pump looks great with a skinny pant, as does a thin-strapped heel. To really exaggerate your leg length, pick a shoe in a nude shade. But since we’re well into fall and closely approaching winter, you’re probably going to want to wear a boot. You’ll either want to select a boot that is tapered at the top, so you can slightly scrunch the pants over them or one with a slightly larger opening but with extra skinny pants. That way that the pants can be tucked in without looking chunky. If it looks chunky, then it will look like you have cankles. No one wants to look like they have cankles. Olivia Caridi was so self-conscious about hers on Ben’s season of The Bachelor, that she ended up stranded alone on an island. So please, don’t inflict such tragedy on your self.

Sam Edelman Halston Heel ($120)

Matisse Vegan Going West Boot ($88)

Vince Camuto Regina Cone Heel Bootie ($148.95)

2. Straight-Leg & Bootcut

There are several different shoe options to pair with a straight-leg or bootcut pant. When the pant hangs over the boot, the hem should be a maximum of half an inch from the ground. Since a bootcut pant looks best with a boot tucked underneath, a sock boot style works great. A straight-leg jean usually looks better cuffed a bit, with either an ankle boot or, with a higher fitted boot such as a sock boot.

RAYE Draper Bootie ($178)

Dolce Vita Bel Bootie ($150)

3. Cropped

I’m no 5’10” supermodel. Meaning, I tend to look terrible in cropped pants. They make my legs look that much shorter and that much stubbier. That being said, our shoe choices can help us combat this problem. To elongate the leg, wear a pair of nude heels with your cropped pants. If you want to wear boots, wear your cropped pants over a taller pair of fitted boots so that the narrowness of the ankle is still visible. Or, you could even try wearing a pair of boots less fitted around the ankle, but with a wider cuff pant. Basically, what I’m trying to say here, is that there’s a lot of ways to style a pair of cropped pants with your shoes so that you don’t look like one of those stout munchkins from The Wizard Of Oz.

RAYE x STONE_COLD_FOX Bacall Heel ($148)

Charles David Iceland Bootie ($99.95)

Jeffrey Campbell Cromwell Suede Cut Out Bootie ($175)

4. Flare

With flare pants, you’ll def want to wear a heel. It never looks good to have your pants dragging on the ground, plus the heel will contribute to a longer looking leg. Look for a shoe with a heel height of about three and a half inches to ensure you look like you have legs for dayssss.

Free People Silver Storm Mule ($128)

5. Wide-Leg & Palazzo

An extra wide-leg pant, such as a palazzo pant, requires a chunkier shoe to help balance out the silhouette and extra fabric. If the shoe is too sleek and small, it will only make your legs look that much bigger. Which like, no one wants, and totally takes away from your outfit.


Jeffrey Campbell Guadalupe Bootie ($190)

Free People Perfect Pair Platform ($178)

At the end of the day, when deciding on what pair of shoes to wear with your pants, take a good hard look in the mirror. Does your outfit look flattering? If so, you probably chose the right pair of shoes. If not, reread this article and try again. Cause like, IDK what else to tell you.

Images: armedshutter/Unsplash; Revolve (5); Nordstrom; Free People (3); South Moon Under (2)
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Shannon McCormick
Shannon McCormick
Shannon McCormick (previously under the alias of 'Betch Dressed') is a self-proclaimed fashion expert with a sick obsession for all things Bravo. She primarily writes about everything fashion, but also dabbles in other areas because she's a talented overachieving Virgo. Follow her on Insta (@shanmccormick) and comment/DM topics you want to hear her incredible take on next!