As a Stylist, Here Are the Shoes I'm Avoiding This Fall (And the Ones I'm Choosing Instead)

      August 29, 2025

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      A few weeks back, I started noticing signs of fall approaching. As someone who doesn’t decorate for Halloween early—or at all, really—my initial thought was that you couldn’t pry my Havaiana flip-flops away from me. However, given my role, I’ve found myself diving into the world of fall fashion, which has led me to browse various sites and quickly change my tune after discovering an array of must-have fall footwear for the upcoming season.

      While I have enjoyed my share of strappy summer sandals this season, I must admit that once I warm up to the thought of cooler weather, my enthusiasm for fall shoes is unmatched. The only comparable feeling is the relief I experience when I slide into a well-worn leather boot, knowing my toes will be protected in the bustling streets of New York for the next several months.

      How I'm assessing my fall shoe collection for a new season

      As I sort through last year's collection of fall shoes, I'm also evaluating the gaps in my lineup and creating my wishlist for the season. As a stylist, I'm accustomed to periodically reviewing my wardrobe. However, as I unpack my fall essentials from storage, it’s evident that I’ve allowed a few things to slip over the years. While I’ve made some commendable shoe choices in the past, I must acknowledge that I’ve also made a few missteps. Stylist or not, everyone is bound to make a handful of questionable wardrobe choices throughout their lives.

      If you find yourself wanting to upgrade some regrettable footwear decisions, learn from my experiences and consider this list of dos and don’ts before stepping (literally) into this fall's shoe trends. It may not solve all your style dilemmas, but it is a productive step toward getting your footwear right this season.

      Skip: Chunky Trainers | Buy: Slim Sneakers

      If you're the type who has a Google Slides folder for vacation outfits (same), you've probably noticed the influx of slim, suede sneakers showcased during last month’s Spring/Summer 2026 shows in Copenhagen. It’s not that dad sneakers are out; they simply don’t balance the oversized and layered looks that are currently in vogue. Following the principle of contrast, a sleeker, more refined sneaker sharpens baggier silhouettes and instantly feels more polished.

      Skip: Ballet Flats | Buy: Slipper Flats

      Ballet flats will always have a place in fashion, but this season’s stylish alternative is the slipper flat. Once just for home wear, this silhouette has now made its way into public view, appearing everywhere from fashion week sidewalks to casual coffee runs. The charm lies in its relaxed, almost effortless vibe that still seems intentional. Pair them with tailored trousers and a trench coat or keep it casual with jeans and a tee. Regardless, they're set to become fall’s most popular shoe.

      Skip: Chelsea Boots | Buy: Sock Boots

      Take a moment with me to discuss Chelsea boots. While sleek, pointed-toe designs still hold their appeal, the classic round-toe versions are starting to feel somewhat dated. Enter the sock boot. Snugging the ankle with its streamlined fit, this season’s trending boot has already won over the hearts of street-style influencers everywhere. They pair perfectly with fall’s midi skirts and puddle-hem trousers, illustrating that sometimes, a refresh is exactly what your wardrobe requires.

      Skip: Traditional Loafers | Buy: Loafer Mules

      Loafers never truly disappear, but they do evolve, and this fall, the loafer mule is taking center stage. Forget the minimal, pointed mules of previous seasons. Designers are embracing boldness with chunky soles, metallic details, and standout finishes that transform a classic into a conversation starter. Think of them as a blend of polished and playful—the ideal balance between office-appropriate and weekend-ready.

      Skip: Round-Toe Heels | Buy: Peep-Toe Heels

      I don’t set the rules, but if I did, peep-toe heels would be a must-have. Fortunately, designers seem to be on the same page. This season's runways unveiled a fresh array of peep-toe styles—from sculpted kitten heels to barely-there straps—that evoke a refined revival of early 2000s designs. Whether crafted as boots, mules, or sandals, this silhouette demonstrates that a subtle peek can be just as impactful as a bold statement.

      Skip: Lace-Up Boots | Buy: Pull-On Boots

      For those who favored lace-up boots in the last decade, it’s time for a change. Pull-on boots—laceless, free of hardware, and endlessly versatile—are stepping into the limelight. The aesthetic isn't rugged farm style; fashion insiders are pairing them with