The Preppy Shoe That's Replacing My Go-To Winter Boots This Season

Originally Published: 
Darrel Hunter
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I always like to ask people what their favorite season is, because I feel like you discover a person's personality depending on their favorite time of year. I personally love the fall and early winter months. From October to December you'll find me embracing all manner of autumnal pleasures: festive lattes, comfy knit sweaters, and all the boots. This year, however, I'm shaking things up as preppy footwear styles have slowly eclipsed the sturdy shoes I typically reach for as soon as the L.A. temps dip below 70 degrees.

I know, for many, lighter classic shoes like loafers, Mary Janes, and Oxfords may seem impractical for chilly weather. However, when layered up with the right hosiery, you'd be surprised how cozy they can be. And, when paired with seasonal staples like oversized wool blazers, warm sweater vests, and buttery leather trousers, you're not only prepped for the chill, but also looking put-together while you're at it.

Maybe it's the steady stream of '80's and '90s rom-coms I've been watching or the preppy trend that's steadily been picking up steam over the past year, thanks to brands like Rowing Blazers, Kule, and Brother Vellies. Or maybe it's a newfound need to shake up my WFH wardrobe. Whatever the reason hidden deep within my psyche, this holiday season is marking the dawn of a new — and preppier — day, for my footwear anyway. Sorry, combat boots and Western styles. The three classic shoes ahead are stealing your thunder right now.

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Preppy Shoes Outfit: Mary Janes

Angela Melero

Nothing is more classic than a Mary Jane. I first came to love this schoolgirl style when I discovered the 1995 cult classic Clueless, where the shoe played a pivotal role in Cher Horowitz's wardrobe. For my 2020 take, I'm doubling down on the prep by pairing the style with a sweater vest and shirt dress. And while Cher liked to wear hers with knee-high stockings, I love a frilly mid-calf or ankle sock in a fun shade to brighten up an otherwise neutral ensemble. It all reads very '90s — in the best way.

Preppy Shoes Outfit: Loafers

Angela Melero

I typically like to wear my loafers á la Meg Ryan in When Harry Met Sally with a knit trouser and blazer. This season, however, I'm giving my loafers a work-from-home makeover, swapping in a straight-leg leather pant and easy button-down. When accessorized with some dainty jewelry, you've got a streamlined ensemble that still feels sophisticated, chic, and very wintery.

Preppy Shoes Outfit: Oxfords

Angela Melero

I'm not going to lie. This look was shamelessly stolen from Carrie Bradshaw, who wore something similar in Season 1 of Sex and the City. I added my own twist by opting for a metallic version of the classic black or brown Oxford. The shiny finish instantly elevates the classic outfit formula, making it a fun option for a virtual holiday party. I love an ensemble — and shoe — that can be relied upon year after year, and never lose its sophistication or cool factor.

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