As a stylist, here are the shoes I'm avoiding this fall (and the ones I'll be purchasing instead).

      August 29, 2025

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      A few weeks ago, I started to sense the arrival of fall. As someone who doesn't decorate for Halloween early—or at all, really—my immediate reaction was, “You couldn’t get my Havaiana flip-flops away from me if you tried.” However, due to my role and the nature of my work, I've found myself immersed in fall fashion, leading me to browse various sites and quickly change my mind after spotting a plethora of must-have fall shoes for the upcoming season.

      While I’ve enjoyed my fair share of strappy summer sandals this year, I must admit that once I embrace the cooler weather, my excitement for fall shoes becomes unmatched. The only comparable feeling might be the comfort I experience slipping into a well-worn leather boot, knowing my toes won’t be exposed on the bustling streets of New York for several months.

      How I’m evaluating my fall shoes for a new season

      As I unpack the fall shoes I wore last year, I’m also identifying what I'm missing and creating my wishlist for this season. As a stylist, I regularly reassess my wardrobe. But after retrieving my fall pieces from storage, it's clear that I've neglected some areas over the years. Although I've made several excellent shoe choices in the past, I acknowledge that I've also made some missteps along the way. Regardless of being a stylist, everyone is prone to a few questionable wardrobe decisions throughout their life.

      If you find yourself wanting to upgrade some of your own regrettable footwear purchases, learn from my missteps and consider the following list of dos and don’ts before diving (literally) into this fall’s footwear options. It might not solve all your style issues, but it is a useful step toward refining your choices this season.

      Skip: Chunky Trainers, Buy: Slim Sneakers

      If you’re the type to have a Google Slides folder dedicated to vacation outfits (same here), you’ve likely noticed the influx of slim, suede sneakers that took the Copenhagen streets by storm during last month’s Spring/Summer 2026 shows. It’s not that dad sneakers are out; they simply don’t mesh well with the oversized and layered looks that dominate current fashion. Applying the rule of contrast, a sleeker, more refined sneaker aligns better with baggier silhouettes, giving a sharper and more polished appearance.

      Skip: Ballet Flats, Buy: Slipper Flats

      Ballet flats will always be a fashion staple, but this season’s stylish alternative is the slipper flat. Traditionally meant for home use, this style has gone mainstream and can be seen everywhere, from fashion week street styles to casual coffee outings. The charm? A relaxed, almost effortless vibe that still feels deliberate. Pair them with tailored pants and a trench coat, or keep it easy with jeans and a tee. Regardless, they’re primed to be the go-to shoe of the fall.

      Skip: Chelsea Boots, Buy: Sock Boots

      Take a moment… we need to talk about Chelsea boots. Although sleek, pointed-toe versions remain relevant, the classic round-toe styles are starting to feel a bit stale. Enter: the sock boot. Snug around the ankle with a streamlined fit, this season’s “it” boot has already captivated street-style icons everywhere. They pair perfectly with this fall’s midi skirts and puddle-hem trousers, demonstrating that sometimes, your closet just needs a refresh.

      Skip: Traditional Loafers, Buy: Loafer Mules

      Loafers never truly go out of style, but they do adapt, and this fall, the loafer mule is taking center stage. Forget the minimal, pointed mules of previous seasons. Designers are opting for bold designs with chunky soles, metallic accents, and standout finishes that transform a classic into a statement piece. Picture 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. Thankfully, designers seem to agree. This season’s runways showcased a fresh array of peep-toe styles—from sculptural kitten heels to minimalist straps—offering a refined revival of early 2000s designs. Whether found in boots, mules, or sandals, this silhouette proves that a subtle reveal can hold just as much impact as a bold statement.

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

      For those who went all-in on lace-up boots last decade, it’s time to simplify. Pull-on boots—laceless, devoid of excess hardware, and incredibly versatile—are stepping into the limelight. The look isn’t rugged