Tobi; American Eagle; Warp + Weft; Topshop; Target

How To Wear Jeans With Heels, Thanks To These 3 Super Trendy Looks

As a gal of only five feet tall, I've pretty much mastered the art of making myself appear taller, and wearing heels is a major part of the fantasy. I don't just wear them on Saturday nights out, though: I'm the girl wearing heeled boots to brunch, or heeled mules to meetings. As a result, I get a lot of questions on how to wear high heels casually; in particular, how to wear jeans with heels seems to be an outfit recipe few of my friends feel comfortable trying out. Whenever they ask my advice, though, I let them know how easy styling heels really is. In fact, pairing denim and heels together is downright easy — the hardest part is learning how to walk in them.

Not convinced that you, too, can casually strut your stuff in some heels? Allow me to change your mind, via three potential outfit recipes utilizing jeans and heels that are just too good to resist. Whether you want to jazz up a dinner date look by throwing on some pumps with your pants, or you're just trying to find the right heeled boots made for walking, the following are some looks to keep in mind when trying out the trend. Before you know it, we'll be shoe-shopping together and exchanging tips on which heels don't hurt after a few laps around the mall (or a few hours at the bar).

The "Casual Boss Babe" Fit

Aldo; American Eagle; Sold Out NYC

When someone's effortlessly chic enough to throw on a pair of heels with an otherwise low-key outfit, I'm always impressed. In fact, I almost always assume the wearer is either Insta-famous or the girlboss owner of her own very successful company — the look screams, "I'm fun and whimsical, but I know how to take charge." The key to nailing this look is rocking fabrics that look high-quality, even when the fit is more casual. American Eagle Mom Jeans ($50, ae.com) are a light wash with ripped knees, but the high-waisted fit, rigid denim, and straight-legged silhouette keep these pants from looking sloppy. Ditch your grubby high school sweatshirt and opt for a more luxe crewneck, like The Bisou Sweatshirt In Cream ($135, soldout.nyc), and pair it all with the Aldo Tenno Mules ($90, aldoshoes.com) in red, white, or black to tie everything together. Now you look like you mean business.

Mom Jean

$50

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American Eagle

The Bisou Sweatshirt In Cream

$135

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Sold Out NYC

Tenno Mules in "Red"

$90

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Aldo

The "What Would Khloé Do?" Fit

Nordstrom; Fashion Nova; Good American; Forever 21; DSW

This look is inspired by denim guru herself, Ms. Khloé Kardashian. Her brand, Good American, has some great styles for anyone looking to rock jeans on a night out, and the Good Legs in "Black001" ($149, goodamerican.com) are a perfect pick if you're not a fan of blue jeans. To put these skinnies into party mode, pair them with the Fashion Nova Clearly A Stud Pumps in "Black" ($35, fashionnova.com), which feature edgy gold accents and a clear material that fakes the look of an open-toe shoe. We aren't wearing open-toed heels in winter, people, so this is as good as it gets! To give these jeans Khlo-up, aka a Khloé-inspired glow-up, pair them with this Topshop Animal Velvet Bodysuit ($35, nordstrom.com) and prepare to accept numerous compliments for rocking the still-hot-and-heavy animal print trend. Top it all off with a leather jacket like this Forever 21 Faux Leather Moto Jacket ($42, forever21.com) so you can stay warm while you look hot, just like Khloé would want you to. If you're really going bold, pair with a red lip and a red bag, like the Urban Expressions Ringo Exposed Zipper Clutch ($30, dsw.com).

Good Legs in "Black001"

$149

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Good American

Clearly A Stud Pump in "Black"

$35

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Fashion Nova

Topshop Animal Velvet Bodysuit

$35

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Nordstrom

Faux Leather Moto Jacket

$42

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Forever 21

Urban Expressions Ringo Exposed Zipper Clutch

$30

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DSW

The "Free Spirit" Fit

Tobi; American Eagle; Warp + Weft; Topshop; Target

Not a skinny jeans gal, never gonna be one? You and me both, sis. I like styles with more exciting silhouettes, and the Warp + Weft ICN Wide Leg Jeans ($98, warpweftworld.com) are some of my favorites, especially in "Fourleaf Clover" a fun, wearable green shade of denim. For a look that works day or night, I'd pair these babies with a simple black top like the AE Plush Lettuce Edge Tank Top ($18, ae.com) and throw the Astr Phoenix Mocha Faux Fur Jacket ($138, tobi.com) overtop, because — and you can quote me on this — teddy bear jackets make any outfit better. As for the heels, I'd opt for a heeled boot with this particular look, like the Universal Thread Leyla Microsuede Heeled Tassel Bootie ($38, target.com) and accessorize with some fun touches, like the SUGARFIX By BaubleBar Resin Hoop Earrings With Druzy ($13, target.com) and the PU Baker Boy Hat ($30, topshop.com). Heeled boots are a great way for any flats-lovers to start trying heeled styles without feeling too out of your comfort zone, and finishing off the look with bold accessories shows confidence in your outfit overall, which will make you feel even better about strutting your stuff in heels.

ICM Wide Leg Denim in "Fourleaf Clover"

$98

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Warp + Weft

Plush Lettuce Edge Tank Top

$12

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American Eagle

Astr Phoenix Mocha Faux Fur Jacket

$138

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Tobi

Universal Thread Leyla Microsuede Heeled Tassel Bootie

$38

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Target

SUGARFIX By BaubleBar Resin Hoop Earrings With Druzy

$13

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Target

PU Baker Boy Hat

$30

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Topshop