These Classic Shoes Have Been Iconic Since Forever; This is How We Style Them
Every fall, I’m overcome by that “back-to-school” feeling. Yet, I haven’t been a student in years. And in some ways, I dread back-to-school season because of the inevitable influx of NYU and FIT students that flood downtown Manhattan.
Although my school days are behind me… I seek to embody some of that unbridled optimism, the fresh-start feeling, and the unjaded youthful enthusiasm. I buy a fresh planner to reset my WFH systems. I reinvigorate my social life to avoid seasonal depression. And I embrace a more academic vibe in my clothing.
I wouldn’t say I’ve gone full Dark Academia. And I definitely don’t subscribe to TikTok’s Old Money aesthetic. But my fall fits are admittedly a bit preppy.
Who can blame me? The Gilmore Girls marathon has begun. I’ve already rewatched Dead Poets Society twice this season. And both Gossip Girl and the Gossip Girl remake are on repeat. All my classic fall shows seem to have a certain aesthetic I just can’t escape.
Loafers have been an academic staple forever. This classic shoe went from being stuffy and square, to the height of fashion.
I rarely thank the Ivys for anything, but it was in their hallowed halls that loafers — often sockless because, you know, 20-something-year-old men — became king. And so preppy fashion and loafers became inextricably linked.
But something most intriguing happened over the past few years. Prep is a less embarrassing aesthetic. I’m not, by any means, heralding what one might call Frat Boy Chic. But young, subversive brands are taking the exclusivity out of the aesthetic and merging it with fringe subcultures to create something that's actually interesting.
Take Aime Leon Dore’s distinctive, elevated streetwear. Take Rowing Blazers as a concept. Take the return of New Balance. And of course, the reign of loafers this season.
So come one, come all! Give me a lug sole! A pointed toe! A pair of scrunched-up white socks!
This look has been approved by the likes of Bella Hadid, Emma Chamberlain, and all the fashionistas I follow on Instagram.
But how does one style loafers? Well, the opportunities are endless. It's best to wholeheartedly embrace the preppy look. Take a cue from the school uniforms of yore and pair them with white shirts, tailored pants, pleated skirts, and blazers. Luckily, this look is all the rage right now — so although you're channeling old-school vibes, you’ll feel right on trend.
But the more audacious way to wear loafers is to pair them with a casual piece such as a sweatshirt. The juxtaposition of a classic shoe with laidback styles is truly surprising. Loafers and jeans are one easily effective pairing.
You might also consider athletic clothes like sweatpants and loafers or loafers and athletic shorts. I’m also partial to loafers with femme pieces like dresses, lacy tops, and long skirts.
TikTok’s favorite stylist, Allison Bornstein, calls these surprising pairings “wearing the wrong shoe.”
TRENDY OR TIMELESS?! what other v categories should we discuss?! #fashiontiktok #fyp #stylist #trendy #timeless #timelessfashion #fashiontok #howtoshop #howtostyle #shoppingtips #howtoinvest #findmystyle #greenscreen
By calling it “the wrong shoe,” she means that going with a surprising shoe choice instead of the obvious matchy-matchy choice adds personality to any outfit. There are no rules! So embrace the styles you’re drawn to and have fun.
This whimsical approach to getting dressed ensures you actually wear what's in your closet. Why not mix structured pieces like loafers with trends and closet staples and the latest trends? You won't have to “save” them for a special occasion or a specific look.
No need to go full dark academia here. It’s all about balance.
Now it's time for you to hunt out the perfect fall loafer. But don’t panic. We’ve narrowed down the endless options and found the best-of-the-best. Here are some of our favorite loafers out there:
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