How to Wear Loafers 11 Different Ways for Any Occasion

I remember my first loafers. Well, they weren't mine, exactly — they belonged to my father. Like boat shoes, only with no laces and appropriate for the office. I would ogle as he shined the leather pair with a fresh coat of polish and glare, enviously, when he'd slip them on and be out the door in a matter of seconds — all while I had to fumble with my sneaker laces or the buckles on my Mary Janes. It wouldn't be until later in life that I'd step out in my own loafer outfits, but the appreciation for the stylish slip-on has lasted to this day.

To preface, I was a '90s kid, not a tween or teen, so while my older sisters (both 8 and 13 years my senior) wore Rachel Green-inspired platform loafers with their checkered skorts, I was rocking light-up sneakers. Luckily for me, loafers are one of those staple shoes that have stood the test of time. Variations of this classic design continue to rotate in and out of closets, and the chunky flat is back in a big way. Still, there's the question of how to incorporate this shoe into our outfit so that it feels fresh and modern? To find out, we turned to some of our favorite street-style stars for inspiration.

Keep scrolling for tips on how to wear loafers for every season, occasion, and style.

As the Ultimate Neutral Shoe

Oftentimes, when we call out a trend, we're showcasing something that will serve as your outfit's statement piece. But footwear is rooted in functionality, and loafers are the ultimate basic, neutral shoe. Purchase a brown, black, or beige pair, and you'll find you can essentially wear them with any ensemble, no matter the cut of your hem, the color scheme of your overall look, or the level of formality.

With High Socks

Loafers and socks go together like peanut butter and jelly. The combo oozes schoolcore vibes, which might give you flashbacks to elementary school, but hey — it's aged pretty well. An easy way to make this pairing a bit more grown-up is by swapping your lacy ankle socks for darker knee-highs. A plaid skirt with a crisp white shirt will contribute to the preppy style, while an oversized denim jacket adds an air of cool.

With a Blazer

Here's an easy fit that is both professional and casual: an unbuttoned blazer and a pair of loafers styled with bottoms based on your mood and the weather forecast. Making this outfit monochromatic will ensure you look sharp and put together, but choosing shoes in a contrasting color is a quick way to pique interest.

With an Oversized Shirt

The no-pants movement has taken off, and we're here for it. Whether it's an oversized button-down, T-shirt, or blazer, the makeshift dress makes classic wardrobe staples feel modern and new. Slipping into loafers instead of sneakers will add a fashion-forward element to an otherwise chill aesthetic.

As a Bracket

The fashion industry saw an uptick in shacket sales between 2022 and 2023 as the shirt-jacket hybrid became popular across social media platforms. However, if you want to do this trend one better, go for a bracket iteration and a pleated mini skirt à la Alexa Chung with pointy-toe loafers to boot.

With a Maxi Dress

Minis aren't the only hemlines ready to collaborate with this must-have shoe. Maxis also look great with chunky sole options. For the finished product to look fresh, fun, and elevated, we recommend opting for socks in the same shade as your footwear or forgoing them altogether for a polished finish.

With Stirrup Leggings

Victoria Beckham's obsession with stirrup leggings has finally caught on, and the '80s fashion trend is making quite the case for why leggings should be considered pants, especially this season. Strengthening the argument is how good the stretchy bottoms look with a pair of loafers. Simply loop the stirrups underneath the heel, add your favorite top and coat, and head out the door.

With Baggy Jeans

Baggy jeans have officially dethroned skinnies (though this writer will never give up her skin-tight bottoms), but if you're envisioning mom jeans circa 1990, think again. Roomier denim isn't dowdy; it's trendy, and looser-fitting styles clean up nicely. Dressing up your pair will ultimately depend on how you accessorize, so if you're aiming for something that's business-lunch approved, slip into a pair of loafers before sliding on a coordinating belt. Matching these two details will tie everything together seamlessly.

With Black Pants

On the list of 'It' items making a comeback, black dress pants are definitely in the top five. Despite being a staple when it comes to work uniforms and formal events, loafers can actually help make this bottom street style appropriate. Coordinating with your favorite button-down and suspenders makes a strong case for embracing menswear.

As Part of Light Academia

Feeling collegiate? The light academia aesthetic is defined by romance inspired by intellectual literature but with a preppy overlay, making loafers its go-to shoe. The closet staple will work to complete nearly every variation of these private school looks — think checked matching sets, button-downs, trench coats, and accessories reminiscent of school days, such as briefcases and pins.

To Offset Bulkier Pieces

Contrary to popular belief, fashion and comfort are not mutually exclusive (thank goodness). In fact, wearing a chunky knit and voluminous skirt with a sleek, slim-fitting shoe — in this case, a loafer — can balance out your stylish ensemble. For a bit more formality, opt for a loafer in a neutral color or match the shade to one that's echoed in an item of clothing for a fun flair.