At this point, my friends should probably join forces to stage a footwear intervention, because my loafer obsession is getting out of control. I have more than a dozen pairs in every possible variety, easily worth a cool four figures in total. My collection of shoes ranges from leopard print pony hair to burgundy patent leather and, of course, several different pairs of plain black loafers. And with fall quickly approaching, your girl is about to enter her fashion prime—along with every other loafer outfit lover among us.
If you, too, are revving up for Loafer Girl Fall, your brain is probably swimming with all the cozy-cute loafer outfit possibilities—those academic-inspired, androgynous-cool 'fits just waiting for a crisp October evening. I'm talking about the kind of autumnal looks Taylor Swift would eat up with a spoon, the types of fall fashion 'fits I've pulled together for your viewing pleasure.
Loafers truly are the ultimate "do everything" shoe, so keep reading for all the cutest loafer outfits to add to your fall/winter 2025 lineup.
With a Classic Trench
In the fashion world, there are few more iconic pairings that loafers and a trench coat. So much so that the girlies have even taken to wearing that pairing with leggings or sweatpants. But I recommend styling yours with dark-wash jeans and gold statement earrings for a casual-glam weekend 'fit.
With Boxers and a Button-Down
When you're trying to give off "impossibly cool in a super effortless kind of way" energy, this is the exact outfit you should be reaching for. Grab a wrinkled button-down (oversized or it's no deal) and a pair of boxer shorts, and style with tube socks and your favorite loafers. It's literally as simple as that.
Rich Auntie Monograms
Pulling off a monogrammed shoe is a power move, and should you choose to partake, you'd better milk it for all it's worth. Double down on the logos with a Eurocore head scarf and a rich-looking tweed suit. From there, just add some gold chains and the designer bag of your choosing to embody the rich auntie you truly are (or the one you aspire to be).
Manic Picnic Dream Girl
Loafer-wearers typically commit to the corp-core bit, but folding them in with other aesthetics is a fun way to give your look a more eclectic feel. For example, paired with a picnic basket and striped shirt dress, your outfit suddenly feels delightfully Scandi-coded.
With a Fitted Blazer and Midi Skirt
This outfit combination is a two-step process for instant chicness—just add a fitted blazer and a voluminous white midi. Most would reach for a pair of slingback heels at this point, but if you're feeling daring, you should try a pair of loafers for a more unexpected touch.
Longline Shorts and a Statement Jacket
Get in loser, we're bringing Bermudas with us into the fall season. Paired with a cool jacket and your best pair of loafers, those longline shorts you basically lived in this past summer can feel appropriately autumnal.
Contrasting Stripes
The typical workwear stripes trope can feel overdone sometimes, which is why print-mixing is key. Pile on varying stripes to keep the look feeling more modern and less 2010.
Country Club Layers
Thanks to the girlies over at Miu Miu HQ, polo shirts and boat shoes are officially part of the zeitgeist again. Embrace that vibe to the highest degree the next time you're coming up blank with your loafer styling.
A Suede Jacket and Flouncy Dress
This outfit is all about unexpected layering—the softness of a tent dress combined with the toughness of a suede jacket and the luxe feel of your loafers creates an all-around interesting look. It's the antidote to any fashion rut you may have gotten yourself into.
A Belted Tweed Coat
I'm going to let you in on a fashion editor secret that few outside the industry know. Every NYFW, we collectively bust this one out when we can't be bothered to pick out yet another outfit. The power of a belted duster jacket and a polished loafer simply cannot be overstated.
Kelsey (she/her) is a freelance digital fashion editor and writer with a knack for turning top-performing content into top-selling content. She has extensive experience in editorial and e-commerce strategy, having worked in both divisions during her years at Seventeen and Bustle. With more than a decade of experience in digital media, she also offers creative and social media consulting, as well as copywriting services. She enjoys cheeseburgers, traveling, and vintage hauls. Follow her on Instagram at @klstieg.
