As a Stylist, Here Are the Shoes I’m Avoiding This Fall (And What I’m Choosing to Purchase Instead)

As a Stylist, Here Are the Shoes I’m Avoiding This Fall (And What I’m Choosing to Purchase Instead)

      August 29, 2025

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      A few weeks ago, I started sensing the essence of fall approaching. As someone who doesn’t decorate for Halloween ahead of time—or at all—I initially thought, “There’s no way anyone could take my Havaiana flip-flops away from me.” However, due to my profession, I’ve found myself immersed in the world of fall fashion, leading me to browse various sites and quickly change my tune upon discovering a plethora of must-have fall footwear for the season ahead.

      While I’ve enjoyed my share of strappy summer sandals this year, I must admit that once I adjust to the idea of cooler weather, my excitement for fall shoes is unparalleled. The only comparable feeling might be the comfort of slipping into a well-worn leather boot, knowing I won’t have to think about my uncovered toes on the streets of New York for many months to come.

      How I’m evaluating my fall shoe collection for the new season

      As I unpack the fall shoe lineup from last year, I’m also assessing what I’m missing and creating my wishlist for the upcoming season. As a stylist, I routinely review my wardrobe. Yet, after retrieving my fall items from storage, it’s evident that I’ve let some areas slip over the years. Although I’ve made several good shoe choices in the past, I’ll confess that I’ve also made some missteps along the way. Stylist or not, everyone is bound to have a few poorly judged wardrobe decisions throughout their life.

      If you find yourself in a similar situation and wish to improve some regrettable footwear choices, take note of my experiences and consider the following dos and don’ts before stepping into this fall’s footwear styles. This list might not solve all your style dilemmas, but it is a step in the right direction for achieving the right look this season.

      Skip: Chunky Trainers

      Buy: Slim Sneakers

      If you’re someone who has a dedicated folder of Google Slides for vacation outfits (same), you’ve likely 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 It’s not that dad sneakers are outdated—they just don’t mesh well with the oversized, layered silhouettes dominating fashion right now. Following the contrast principle, a sleeker, more refined sneaker complements baggier proportions and instantly appears more polished.

      Skip: Ballet Flats

      Buy: Slipper Flats

      Ballet flats will always have a role in fashion, but this season’s chic alternative is the slipper flat. Once meant only for lounging at home, this style has officially made its way into public view. It can now be seen on the streets during fashion week and even casual coffee runs. What’s appealing? A relaxed, almost effortless vibe that still feels intentional. Pair them with tailored trousers and a trench coat, or keep it casual with jeans and a tee. Regardless, they’re poised to be the go-to shoe for fall.

      Skip: Chelsea Boots

      Buy: Sock Boots

      Let’s take a moment for Chelsea boots. While sleek, pointed-toe versions still have their place, the classic round-toe style is starting to feel a bit stale. Enter the sock boot. This season’s “it” boot, which hugs the ankle with a streamlined fit, has already caught the eye of street-style stars everywhere. They’re the perfect match for fall’s midi skirts and puddle-hem trousers, demonstrating that sometimes a little refresh is exactly what your wardrobe needs.

      Skip: Traditional Loafers

      Buy: Loafer Mules

      Loafers never truly vanish, but they do evolve, and this fall, the loafer mule is taking center stage. Ditch the minimal, pointed mules of previous seasons. Designers are now getting bold with chunky soles, metallic details, and standout finishes that transform a classic into a statement piece. Consider them as a blend of polished and playful—the ideal compromise between professional and weekend-friendly.

      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. Fortunately, designers seem to share this sentiment. This season’s runways showcased a new wave of peep-toe styles—from sculptural kitten heels to barely-there straps—that feel like a refined revival of the early 2000s versions. Whether they come as boots, mules, or sandals, this silhouette illustrates that a subtle reveal can be just as impactful as a bold statement.

      Skip: Lace-Up Boots

      Buy: Pull-On Boots

      For those who embraced lace-up boots over the past decade, it’s time to simplify. Pull-on boots—free of laces and hardware, and incredibly versatile

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As a Stylist, Here Are the Shoes I’m Avoiding This Fall (And What I’m Choosing to Purchase Instead)

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