Casual Style

How to Wear Casual Heels Like a True Fashionista

by Laura Lajiness


Heels are synonymous with professional workwear pieces like suits, pencil skirts, and sheath dresses, but when you think about how to wear casual heels, it’s hard not to feel overly dressy off the clock. There’s just something about off-duty outfits that makes us equate comfy-chic with flat soles. Typically, many casual outfit formulas involve some sort of flat shoe, whether you’re a sneaker fan, love ballet flats, or routinely rely on slip-on sandals. But as modern dress codes evolve, relaxed pieces of clothing can go farther with the right accessories—and knowing how to wear casual heels is one easy way to make those “off duty” pieces feel like wear-anywhere items.

Whether you’re crazy about denim, love multipurpose dresses, or prefer easy tops and comfortable bottoms, check out these tips for wearing three different types of casual heels for a relaxed-yet-elevated result.

1. Classic Pumps

There are certain essential shoe styles that defy the seasons, and pumps are undoubtedly one of them. The universally flattering silhouette is always polished and elongating, whether you prefer a wear-everywhere nude shade, classic black, or a pop of color.

When it comes to pumps and wearing them casually, the timeless silhouette looks iconic with everything from skinny jeans and button-down shirts to cropped pants and T-shirts to casual dresses, bringing just a touch of polish to relaxed separates. You can even wear pumps with shorts—in this case, it’s best to choose a top with sleeves as a sophisticated counterbalance to a shorter hemline. Another great aspect about pumps is that they come in a range of heel heights so you can choose from walkable kitten heels for a slight lift, two-inch styles when the mood skews dressier, and three- or four-inch silhouettes for real drama.

Pink Scalloped Suede Pumps

2. Strappy Sandals

Innately formal, strappy sandals are an easy and unexpected way to dress up casual pieces like jeans and slim-fit pants, whether you choose a colorful spring shade like soft pink or a patent leather style in a neutral color like nude or black. Whether it’s a peep-toe silhouette or barely there shape, the flash of skin from a strappy sandal is stylish and understated with pants instead of shorter hemlines and breezy skirts and dresses, which feel a bit more dressed up. Plus, they’re the perfect shoe for showing off a gorgeous pedicure in the season’s warmer temperatures.

Pink Suede Strappy Heel

3. The Little Black Bootie

Just like the little black dress, a little black bootie is a hero when it comes to wearing heels casually. Bringing an edgy and unexpected finish to feminine dresses and skirts, a black bootie looks just as great with ankle-length jeans, pants, and jumpsuits. It’s all about choosing clothes in more casual fabrics and fits to avoid that overly dressed up feeling; in the case of dresses and jumpsuits, cotton, linen, or jersey materials will create more of a relaxed look with a heel, whereas T-shirts and blouses will feel perfectly at ease with jeans or ankle-length pants.

Black Laser-Cut Peep-Toe Booties

Featured in this article:

Scalloped Suede Pumps, $130

Suede Strappy Heels, $115

Laser-Cut Peep-Toe Booties, $165

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