(The Shopping List)
These Penny Loafers Will Instantly Elevate Your Everyday Fall Outfit Formula
They’re a classic for a reason.
The trees are just about bare, talk of the holidays is growing louder, and the urge to start shopping those early Black Friday deals can only mean one thing, we are in the prime of fall. It’s time to pull out your favorite trench coat, an oversized sweater, your best denim, and of course, the perfect fall footwear: the loafer.
Indeed, the preppy shoe is a classic that dates back to the 1930s, when the terms was first used. Since then, countless brands have reinvented the style — known for its signature slip-on silhouette, low heel, apron toe, and suede or leather material — over the years to keep up with ever-evolving fashion trends. Each decade brings new interpretations of this timeless silhouette, proving its reigning power.
The sustaining magic of loafers likely lies in its versatility. They pair perfectly with just about anything — jeans, a casual mini dress, formal suiting — the options are endless. They instantly elevate your look and once they’re properly broken in, they increase in their comfort and wearability. (For example, my own pair took about three full day wears before becoming my go-to.) Add a cozy sock, and you’re set.
Whether you prefer a classic design, or something a bit bolder, we’ve got you covered. Shop 12 chic and timeless loafers ahead.
I’ve owned these beautiful Miu Miu shoes for almost three years now, and they’ve truly proven to be an incredible investment in that they remain in almost perfect condition.
Color blocking was seen all over FW25 and SS26 runways, so why not bring that trend into footwear? Cole Haan is a great place to start as the brand is both affordable and known for its quality materials making their shoes durable and comfortable for longterm wear.
Ralph Lauren is a cult classic, and you can never go wrong with a pair of their black leather loafers.
The rich color way of these shoes is a selling point in itself, but the high-quality leather and five-inch foam padding add that extra comfort bonus that pushed them higher on my holiday wishlist. Imagine pairing them with your favorite leather jacket, blouse, and trousers — you’ll look like you just stepped off a flight from Europe.
Animal print isn’t going anywhere, and these pony-hair zebra print shoes from Valentino are just the thing to make a statement with any look.
The Row is adored for its understated elegance and impeccable craftsmanship. This pair of loafers stands out to me in particular for the refined leather tassel accent on the top of the shoe.
Aldo has really been stepping up its shoe game, and this trendy pair of loafers is proof. Dress up the style with a midi dress and a cardigan or down with a pair of trousers and a t-shirt. Plus they’re just under the $100 mark, making them a no-brainer for fall.
Red bottoms will always be in style, and this shoe is an elevated take on the classic penny loafer. I love the scalloped, ribbon-like detail along the thong of the shoe, it adds such a unique, and interesting touch.
Like snake, tiger, or leopard print, cow print is another animal inspired pattern that brings a fun, funky twist to your look. Its neutral tones keep it versatile, while the unique design adds a bold edge.
Ivory or white loafers are a fresh, contemporary alternative to the classic black or brown. Their effortless modern appeal complements an array of looks, whether that be an oversized sweater paired with a silk skirt or a rugby top and casual denim.
The iconic G.H. Bass Penny Loafer was first introduced in 1936, meaning this timeless style has been on the market for nearly 90 years. If that doesn’t say something about timelessness, I don’t know what does.
Leopard is essentially a neutral these days. The warm and earthy browns pair beautifully with practically any color. Whether your style leans grungy, modern, or whimsical, leopard will fit right in.
