The Preppy Socks With Loafers Combo Is Foolproof

While recently scrolling through Instagram, I stumbled upon a photo of Hailey Bieber flaunting a coveted fall shoe trend and a classic styling trick. The Rhode founder wore slouchy white mid-calf socks tucked into leather loafers—a preppy pairing that, alongside sheer knee-high socks, is having quite a moment among the fashion crowd. Although this style is heavily coded with schoolgirl uniform references, Bieber gave it a grown-up twist with a classic trench coat, a sleek black tote bag, and her signature oval-shaped sunglasses. The elevated approach led to fervently searching for other polished loafer outfits to pin to my fall fashion mood board.

Bieber is just one of the many celebrities who can’t get enough of this foolproof footwear formula. Not too long ago, Kendall Jenner wore her version of the academic-inspired look, coordinating her socks and loafers with a sharp leather jacket, a midriff-baring white baby tee, and belted Bermuda shorts. Meanwhile, Jenna Ortega took the style for a spin with an oversized blazer and a thigh-grazing mini skirt.

Along with A-listers, street-style pros have also provided plenty of lessons on properly wearing socks with loafers this season. During this past fashion month, It girls embraced the trend with fall essentials like plush cardigans, cozy cable knit sweaters, and double-breasted coats.

The combo is the perfect high-style solution as temperatures drop if you don't want to pull out your tights just yet. Here, I’ve compiled a straightforward guide on how to style the loafer and socks combo.

Layer on the Leather

It’s no secret that fashion insiders are obsessing over leather bomber jackets. This retro style—defined by its often oversized silhouette and sleek zip-up closure—is practically on every street corner. Combine this look with a pair of leather loafers; for an extra pop, you can match the shade of your socks to your T-shirt.

It's All in the Details

Notice how this fashionista meticulously tied the color palette of her socks and loafers into the rest of her refined outfit. Follow suit by pairing an oversized white tee with a short-cut black mini skirt and a sweeping black leather trench coat. Don’t be afraid to break up the contrast with a light gray turtleneck sweater.

Paint the Town Red

Recently, style experts have been raving about the “unexpected red theory.” It’s a design phenomenon that states that a pop of red can pull together any look, and after taking one glance at this outfit, you'll totally get the hype. Lean into a vibrant shade of cherry red with a Yankees baseball cap, or choose a pair of fiery socks instead.

The Knee-High Agenda

No, you’re not imagining things—trendsetters everywhere are indeed wearing sheer socks up to their knees, and many of them are pairing their hosiery with loafers. While this playful style might feel a bit intimidating, it doesn’t have to be. Reference this outfit and slip into a fitted top, a roomy cardigan, and a pair of shorts with extended hemlines.

The Trusty Trench

Temperatures are hovering around 50 degrees, and you’ve just placed an order at your local coffee shop for a pumpkin spice latte. Yep, it’s officially fall, and it’s time to dust off your go-to trench coat. Ground your look in a pair of lug-sole loafers styled over ribbed socks, and consider wearing a striking fall dress that will make heads turn.

A Layered Look

There’s much to love about this look, but what stands out the most is the intricate way each piece is layered. You can follow the shirt sandwich dressing approach by tucking a crisp button-down shirt into a frilly midi skirt and adding a button-down coat. Add a pair of frilly socks to incorporate some fun texture.

She Means Business

For a day in the office, put your best foot forward with platform loafers that will give you a boost of confidence. If you must brave the cold during your morning commute, bundle up in a durable coat stitched with insulated fabric, a midi or maxi skirt that offers leg coverage, and a pair of crew socks.

In Burgundy We Trust

If there’s one thing for sure, it's that burgundy won’t quit. It’s one of fall 2024’s hardest-working color trends, and it gets the job done every time. Wear it as a leather jacket, and pick subdued shades for the rest of your outfit. Take things to greater heights with elevated loafers that rival sky-high platforms.

Warm Tones

Brown will always stand the test of time as a quintessential fall shade, and now is the time to layer on the chestnut, caramel, and espresso hues from head to toe. To master an easy all-brown outfit formula, try a wool-blend scarf coat, plush socks, and sophisticated leather loafers. As for what to wear underneath your layers, that's up to you, but a chunky sweater and wide-leg tailored trousers are always an easy formula that delivers.

For the Party Girl

Loafers paired with socks work for the office, but there are ways to give this combination more of a festive feel. For your next going-out outfit, slip into a shimmering mini skirt, a white button-down shirt, and a denim barn jacket trimmed with leather collars. Then, sit back and wait for the compliments.