Hyperbole or not, to work or live in Manhattan, you’ve got to get comfortable with walking. There have been days in the city where I’ve logged well over 5 miles on foot—usually lost in a song, strutting down 5th Ave like it’s my own personal runway. It’s a known fact that New Yorkers walk fast, so to keep up with this city’s stride, it’s essential that whatever is supporting your soles must provide comfort as well as style—so, coming to you as a shopping editor, an NYC commuter, and a previous Manhattan resident, here is my City Girl’s guide to fall shoes in 2025.
I’ve called on the latest Gen Z fall 2025 shoe trends—like the sporty sneaker, slouchy boot, and casual pump—plus two Parisian fall favorites, the slim loafer and the suede ballet flat. The classic Birkenstock Boston Clogs make an appearance, alongside the cult-favorite Frye boots. Join me as I try on, style, and review these seven NYC editor-approved fall shoes.
My pick: Madewell Mylie Ballet Flats ($128)
First up: the Madewell Mylie Ballet Flats. With a few sizes already out of stock (the 5, 6, 10, and 11), these are bound to sell out fast. I’d seen these soft suede ballet flats on IG and wondered if they’d hold up on NYC’s busy streets. I got to try them out for a few weeks, and I can officially report: these are a fall 2025 ballet-flat must-have. The 100% leather upper survived Penn Station at rush hour, subway delays, and spontaneous dinners with friends. I’ve reached for these chic suede flats again and again because their mocha finish has become my new fall neutral.
Here, I’ve opted for a casual sweater-and-jean ensemble with my favorite pair of Levi 501s and a thrifted lime-green wool turtleneck. I matched the dark carob Madewell flats to a woven brown leather bag. This is just one of the many ‘fits I styled around these flats. I think they’d look adorable with a pair of barrel-leg trousers and an oversized blazer. So if you’re looking for a new ballet to add to your fall shoe rotation, I’d highly recommend the Madewell Mylie.
Madewell
The Mylie Ballet Flat
With no half-sizing available, I recommend sizing up if you are in between sizes. The flat’s 100% leather lining molds to you for a snug fit. And as true size eight, the corresponding size fits me perfectly. I’m a chronic complainer of sore feet, but I found these Madewell flats a relief on my Manhattan commute.
If you’re looking for a new pair of jeans, I recommend starting with the Levi 501s. The fit is a classic. Shop a similar sweater from Pistola and a woven-leather tote from Anthropologie below.
Shopbop
Pistola Adina Sweater
levi
501 Original Fit Jeans
Anthropologie
Woven Faux-Leather Tote
My pick: Adidas Tokyo Shoe ($90)
Low-profile sneakers are one of the biggest fall 2025 sneaker trends. Fashion people everywhere are opting for a slimmer, sportier trainer to wear with trousers and jeans this fall. If you’re a frequent WWW reader or like to take note of what fashion people are wearing, then my low-pro sneaker of choice won’t come as a surprise: the Adidas Tokyo Shoes. Perfect for a casual outing or, depending on you’re ensemble, easy to dress up—these ’70s-inspired runners prepare you well for city life.
I’ve leaned into the sporty-chic aesthetic, pairing these low-pro lace-ups with Reformation’s low-rise trousers and a basic white tee. I could also see these with a wide-leg baggy jean. Or even a cute pair of socks and an equally retro-chic shift dress for a flirty, yet sporty look. The styling possibilities are endless, and certainly don’t end with fall ‘fits. These rubber soles will look chic well into 2026.
The soft suede upper is a great textural addition to any fall look. I found the size eight a bit roomy, but with a cozy pair of socks, they fit just right. Available in 12 different colors, from the off-white and deep black, seen here, to a mirror-finish metallic. Half-sizing is available from 5 to 11.
Shop the Vida Low Rise Pant from Reformation and a similar white tank below. I’ve also included a pair of silver-toned earrings because leaving the house with jewelry on feels wrong.
Gap
Organic Cotton Vintagesoft T-Shirt
Reformation
Vida Low Rise Pant
Ettika
Heirloom Twist Small Hoops
My pick: Seychelles Mocktail Mule ($122)
I’ve written before that growing up, I expected to wear more heels in my adult life. But this has proved to be more difficult than anticipated. Working in Manhattan, one of the main criteria for my footwear is comfort, and high heels aren’t exactly known for their soothing support. This low-heeled mule is my alternative to a sky-high pump without sacrificing style for comfort. I purchased the Seychelle Mocktail Mule at the start of fall, and have since worn them to NYFW showings, diners, and screenings, proving to be a reliable choice of footwear.
The tapered square toe creates a lovely silhouette when paired with a column skirt. I’m a fool for clean lines and a vintage-inspired elegance. I styled the midi skirt with a solid white tee layered under a sheer black sweater because see-through knits are my fall continuation of the sheer trend that dominated the style set’s wardrobe this summer. You can shop the low-heeled mules at a discount on Revolve for only $122.
Sold out in sizes 6.5 and 9, these slip-on mules barely qualify as heels with their 1-inch lift. The barley-there pump is an evolution of the fashion crowd’s love for kitten heels and ballet flats. It took me about a week to break in the leather upper, but after that, these are one of the more comfortable mules I own.
Below is a recreation of my look with similar finds. A semi-sheer alpaca short-sleeve cardigan from Everlane, a basic cropped tee from H&M, and another Everlane pick, a column skirt
Everlane
The Air Alpaca Short-Sleeve Cardigan
H&M
Microfiber Cropped T-Shirt
Everlane
The Dream Maxi Skirt
My pick: G.H. Bass Whitney Leather Loafer ($175)
Next up, the loafer—the collegiate silhouette is a fall classic, loved by both Parisians and New Yorkers. The shoes’ legacy and influence on the fashion set are unavoidable. Before deciding on which loafer to test out, I consulted my fellow Who What Wear editors and discovered a common theme—the G.H. Bass Whitney Leather Loafer. I tested and styled the penny loafer to find out why the G.H. Bass ones are an editor fave.
Crafted from premium box leather, the G.H. Bass loafers only get better with wear. Available in four finishes, I opted for wine. While still the traditional silhouette, the burgundy finish is a modern rendition of the OG black loafer. The polished leather truly shines when paired with elevated basics. That’s why I styled them with a classic white button-down, Levi 501 Curves, and a buttery-soft leather shoulder bag.
G.H.BASS
Whitney Leather Loafer
Available in half sizes from 5 to 11, the G.H. Bass Whitney Leather Loafer is a fashion person’s must-have. They’re an editor-favorite for a reason–the quality, the fit, and the finish. It takes a few wears to break in, but once you’re past that stage, these elegant loafers will be you’re new fall go-to.
If you’re interested in replicating my look, here are some similar fall finds, plus the exact Levi 501 Curve I own.
Gap
Vegan Pebble Leather Slouchy Bag
My pick: J.Crew New Stevie Knee-High Boots ($348)
The fall weather in NYC is unpredictable. One day it’s mid-70s, the next is low 50s. Make it make sense! But my favorite fall outfit formula for the temperamental forecast is a knee-high boot and a mini dress. I tried these J.Crew New Stevie Knee-High Boots in suede black in store a few months ago, and absolutely fell in love. I got to test them out for a few weeks, and they’ve become a fall favorite. The kitten heel is ultra-comfortable, the soft suede looks just as new as the day they arrived, and the midnight black boot is so easy to style.
I’ve paired the knee-high boots with a Theory plaid dress I grabbed from TheRealReal a few years ago. (Plaid is undoubtedly having a moment this fall, ask any Who What Wear editor.) I finished the look with some gold chain bracelets and a Coach shoulder bag.
j.crew
New Stevie Knee-High Boots
With any boot, I recommend sizing up. The suede style comes in three finishes: Black (as shown here), Blonde Espresso, and Perfect Chocolate. These look great pulled high, but you’ll look like a real fashion insider if you slouch them down for an edgy look.
If you’re feeling the plaid vibe, check out this under-$90 Gap shift dress. Shop a similar Coach bag and chain bracelet to the one I wear below.
Gap
High-Neck Mini Shift Dress
Sophie Blake
14k Noah Rollo Bracelet
My pick: Birkenstock Boston Soft Footbed ($170)
I’ll be honest, I never understood the Birkenstock hype—that is, until I tried out the Boston Soft Footbed Clogs. After wearing these for a few weeks, I found them a staple in my work bag. I’d wear them on my commute, switch into different shoes for the workday, then pull these right back out of my bag (Mary Poppins-style) come quitting time. They are, in fact, as comfortable as people say. I’m a big fan of the Basalt Grey Tonal. I think it’s a chic alternative to the traditional beige I often wear. It’s official, I’m a true Birkenstock convert.
I found these clogs a breeze to style. Mimicking their relaxed look, I wore them with like pieces: my Levi 501 Curves, a boatneck long sleeve, and a dark grey turtleneck, draped casually over my shoulders. I recently saw Kendall Jenner style her sweater like so, and I’ve been doing it ever since.
BIRKENSTOCK
Boston Soft Footbed
If you’ve been looking at a pair of Boston Clogs, but haven’t made the decision yet, this is your sign. Available in over 10 colors—from deep blues to antique whites—I’m certain you will find a pair that speaks to you.
Here’s how to recreate my look: a similar boatneck long-sleeve and grey turtleneck, and of course, the Levi 501 Curve. (Can you tell I love my Levi jeans?).
aritzia
HomeStretch Rib Boatneck Longsleeve
Nordstrom
Wool & Cashmere Turtleneck
My pick: Frye Campus 14L ($498)
The cult-favorite Frye Campus 14L is a staple in any cool-girl wardrobe. I’ve seen It-girls wearing this boot with everything from micro shorts to midi skirts to retro-inspired flares. The knee-high leather boot is a smart investment in fall footwear. The quality construction and timeless look will have you reaching for these boots for years to come.
I’ve paired it with a thrifted denim skirt, a draped off-the-shoulder Free People top, and a two-tone ring stack. If you’re feeling the boho-chic fall aesthetic, then these boots should definitely be on your radar.
With any boot, there is a break-in period, so make sure you have a pair of thick socks on hand. The sizes range from 5.5 to 13, with limited half-sizing available. With sizes 5.5, 6, 7, and 13 already sold out, I’d act fast, or check out the other 13 gorgeous colors available.
Shop the Free People set, my top is from, a similar denim midi skirt, and a two-tone ring stack that is currently in my Shopbop cart.
Free People
Good Feels Sensual Set
Bardot
Jonah Midi Denim Skirt
