A few weeks ago, I began to hear some rumblings of fall. Being the girl that doesn’t decorate for Halloween early—or at all, for that matter—my first thought was “you couldn’t pry my Havaiana flip-flops out of my hands if you tried.” But being who I am and doing what I do, I’ve been thrust into a world of fall fashion that has me prematurely perusing the sites and very quickly eating my words after seeing an abundance of can’t-miss fall shoes for the upcoming season.
While it’s true that I’ve reveled in my fair share of strappy summer sandals this season, I have to be honest. Once I’m properly warmed up to the idea of cooler temps, my level of excitement for fall shoes is unparalleled. Maybe the only feeling in comparison is the relief I feel after slipping into a worn-in leather boot and not having to worry about my exposed toes in the streets of New York for the next several months.
How I’m auditing my fall shoes for a new season
As I unpack last year’s fall shoes rotation, I’m simultaneously assessing the gaps and determining my wishlist for fall. As a stylist, I frequently audit my wardrobe. But after pulling out my assembly of fall gear from storage, it’s clear that I’ve let a few things slide over the years. Though I’ve made several commendable shoe choices in the past, I’ll admit I’ve also made some mistakes along the way. Stylist or not, everyone is destined for a handful of miscalculated wardrobe decisions in their lifetime.
If you find yourself in a similar position of wanting to upgrade some regrettable footwear purchases of your own, learn from my mistakes and consider the following list of dos and don’ts before dipping your toe (literally) into this fall’s footwear. It might not be the end-all solution to your style woes, but it is one step (I’m on a roll) toward getting things right this season.
Skip: Chunky Trainers
Buy: Slim Sneakers
If you’re the type who has a folder of Google Slides dedicated to vacation outfits (same), then you’ve probably clocked the flood of slim, suede sneakers making their way through Copenhagen during last month’s Spring/Summer 2026 shows. It’s not that dad sneakers are over. They just don’t quite balance the oversized and layered silhouettes dominating fashion right now. Following the rule of contrast, a leaner, more refined sneaker sharpens up baggier proportions and instantly feels more polished.
Skip: Ballet Flats
Buy: Slipper Flats
Ballet flats will always have a place in the fashion canon, but this season’s chic alternative is the slipper flat. Once reserved for bedside wear, the silhouette has officially gone public. It’s now been spotted everywhere from fashion week streets to low-key coffee runs. The appeal? A laid-back, almost undone vibe that still feels intentional. Wear them with tailored trousers and a trench coat, or keep it casual with denim and a tee. Either way, they’re set to be fall’s most-worn shoe.
Skip: Chelsea Boots
Buy: Sock Boots
Take a deep breath… we need to have a moment with Chelsea boots. While sleek, pointed-toe versions still hold their own, the classic round-toe pairs are starting to feel a little tired. Enter: the sock boot. Hugging the ankle with a streamlined fit, this season’s “it” boot has already captured the hearts of street-style stars everywhere. They’re the ideal partner to fall’s midi skirts and puddle-hem trousers, proving that sometimes, a refresh is exactly what your closet needs.
Skip: Traditional Loafers
Buy: Loafer Mules
Loafers never really disappear, but they do evolve, and this fall, the loafer mule is stealing the spotlight. Forget minimal, pointed mules of seasons past. Designers are going bold with chunky soles, metallic hardware, and statement finishes that turn a classic into a conversation piece. Think of them as equal parts polished and playful—the perfect middle ground between office-ready and weekend-worthy.
Skip: Round-Toe Heels
Buy: Peep-Toe Heels
I don’t make the rules, but if I did, peep-toe heels would be non-negotiable. Luckily, designers seem to agree. This season’s runways brought a fresh wave of peep-toe styles—from sculptural kitten heels to barely-there straps—that feel like a refined revival of the early aughts versions. Whether in the form of boots, mules, or sandals, the silhouette is proof that a subtle peek can feel just as powerful as a bold statement.
Skip: Lace-Up Boots
Buy: Pull-On Boots
For anyone who leaned hard into lace-up boots last decade, it’s time to simplify. Pull-on boots—laceless, hardware-free, and endlessly versatile—are stepping into the spotlight. The vibe isn’t rugged ranch life, though. Fashion insiders are styling them with feminine slip dresses, satin skirts, and oversized knits for a look that feels equal parts soft and strong.
Skip: Black Shoes
Buy: Burgundy Shoes
While black will forever be a staple, this fall is all about its moodier cousin: burgundy. Designers showed the shade in every form imaginable—from sleek thigh-high boots to everyday Mary Janes—and contemporary labels are quickly following suit with more affordable versions. Rich, versatile, and surprisingly neutral, burgundy is the color that will instantly make any outfit look more intentional.
Tinsley Crisp, Fashion & Beauty Staff Writer
Tinsley Crisp is a Fashion & Beauty Staff Writer at The Everygirl and specializes in reporting on the season’s latest trends and hottest products. As a New York City-based stylist, she’s committed to injecting joy into the art of getting dressed and delivering attainable yet aspirational content to our readers.
