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Must Have Fall & Winter Shoes for 2025: Boots, Loafers, and Cold -Weather Style
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items Step into the season with the best fall and winter shoes for 2025—tall boots, loafers, clogs, sneakers, and more. These stylish picks combine comfort and trend, making them essentials for cold-weather dressing.
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Sections
6
Clogs & Mules
Tall Boots
Short Boots
Wide Calf Boots
Flats
Sneakers/Tennis Shoes
Clogs & Mules
Cozy meets chic with clogs and mules that transition effortlessly from home to street style. Perfect for fall layering, these picks bring texture, comfort, and on-trend appeal to any outfit.
The UGG Goldenstar Clog is everywhere this fall—and for good reason. It’s cozy, cute, and actually comfortable enough to wear all day. If you're into the shearling, clog, and comfy-core trend, this is a must-have for your fall/winter shoe lineup.
UGG | Women's Goldenstar Clog
This limited-edition silhouette updated the original Goldenstar with UGG’s braided heel strap—a stylish twist that’s already trending. I recommend sizing up at least half a size for everyday socks or thicker layers—these do run small compared to UGG ...
UGG | Women's Goldenstar Braid Clog
The UGG Goldenstar Villa Clog in Chestnut is your effortless “I woke up like this” fall shoe—it feels casually refined and is perfect for 2025 cold-weather dressing. Crafted from supple nubuck leather with an ultra‑light Sugarcane EVA™ midsole and ou...
UGG | Women's Goldenstar Villa Clog
The Steve Madden MELLOW Cognac Suede Slingback Platform Clog is a standout pick for Fall & Winter 2025, combining retro platform vibes with modern comfort. Crafted in soft cognac suede and elevated on a 2‑inch platform, these clogs deliver a poli...
STEVE MADDEN | MELLOW Suede Women's Slingback Platform Clog
The Birkenstock Boston Soft Footbed Clogs are easily the most comfort‑obsessed fall pick for 2025. With a velvety suede upper and a cushy latex‑infused wedge over cork, this version delivers instant, break‑in‑free comfort—plus generous arch support a...
Birkenstock Women's | Boston
The Birkenstock Boston Big Buckle Clog delivers the classic Boston silhouette with an uplifting twist—an oversized, gleaming buckle on premium nubuck leather that transforms laid-back footwear into a statement piece.
Birkenstock Boston Big Buckle Clogs
Cozy meets cool in the Birkenstock Naples Suede Clogs — a fresh take on the classic Boston style. These slip-ons feature soft suede, a deep footbed, and a slightly more structured silhouette that makes them feel just a little more polished (but just ...
Birkenstock Naples Suede Clogs
Love that the inside is lined with cozy faux sherpa, so they’re as comfy as they are cool—you’ll basically feel like you’re walking on clouds
Autumn Studded Platform Clogs
Tall Boots
Sleek and statement-making, tall boots are the ultimate cold-weather power move. From classic riding boots to weatherproof rain styles, they’re built for warmth, style, and major outfit versatility.
Love Franco Sarto - they last for multiple seasons and a ton of wear from my experience with other shoes I own from them. They can be on the pricier side, but if you know it's a style you love and personally find timeless, they are a good mid level i...
Franco Sarto | Meyer Knee High Boot
A vegan leather boot that would compliment a ton of outfits. Classic silhouette that you really can't go wrong with. If you aren't looking to break the bank, this is a solid choice price wise and seems to get put on sale regularly
Lulus | Special Someone Dark Brown Suede Over-the-Knee Boots
The khaki color goes hard and you can't convince me different. This boot will standout no matter which color but I think the khaki is so unexpected.
Jeffrey Campbell | OVERLOOK-2
Here is an affordable option for the trendy girlies. They may not be the “it” shoe next season, but they are priced accordingly so you don't feel bad if you only get a couple of solid uses out of them. The foldover detail isn't for everyone and I thi...
madden girl | Evannder Women's Fold-Over Boots
Rain-proof royalty, in your feed: these Women’s Original Tall Rain Boots by Hunter are a must-have—handcrafted from FSC®-certified natural rubber, fully waterproof, and built to brave stormy days in iconic, minimalist style
Hunter | Women's Original Tall Rain Boots
Short Boots
Short boots are the everyday heroes of your fall/winter wardrobe. They pair effortlessly with jeans, dresses, and skirts, offering endless styling potential in compact form.
He makes shoes for the girlies - enough said. But seriously these are most likely going to be my next purchase. My Chelsea boots from last fall cracked at the sole and I am in desperate need before autumn hits. I mayyyyyy wind up with both the black ...
STEVE MADDEN | CHARGES Brown Distressed Platform Bootie | Women's Booties
I also really like these from Sam Edelman and we know the quality will be there. I also really like that the loop detail is on the front and the back. Not something I thought about, but I do think it ties it together nicely.
Sam Edelman | Laguna Waterproof Lug Sole Chelsea Boot
Although the shape and the heel are *chef's kiss* I wish they were in black. I may just need to do a little exploring on the website, but saw these on Pinterest and were immediately drawn to them.
Kyleigh Boots Brown
Looking for a shoe with some more detail? I love the metal ring against the suede. A really cute mix, especially with a cropped jean or skirt.
Franco Sarto | Flexa Elia Ankle Bootie
Now it would not be a millenial made list wthout a Jeffrey Campbell shoe somewhere on the list…maybe a few honestly. From the Lolitas to now I will be a stan of Jeffrey Campbell forever. They aren't always practical but they are stunning, well made a...
Jeffrey Campbell | TAKEOFF
Wide Calf Boots
Say goodbye to the struggle—wide calf boots deliver comfort, fit, and style in one. These picks are perfect for layering over jeans or pairing with dresses without sacrificing ease of wear.
These are the kind of wide calf boots that actually make me want to wear tall boots again. The chocolate leather is so good, and the shape feels elevated without being overdone. I love that they look like they’d work with everything—chunky knits, swe...
Dolce Vita | Gyra Extra Wide Calf Boots
These boots are giving me all the fall feels. The Daria's sleek silhouette and subtle whipstitch details make them feel elevated without trying too hard. I love that they have a comfy block heel and a pointed toe—perfect for adding a little edge to c...
Journee | DARIA COWGIRL BOOTS IN X-WIDE CALF
The rich cabernet red leather is so luxe, and the pointed toe adds just the right amount of edge. The wide calf fit is a game-changer—no more squeezing into boots that don't fit and praying the zipper doesn't break or pinch your leg.
Sam Edelman | Sylvia Wide Calf Knee High Boot
A handful of colors and finishes to choose from these are the staple investment pair for sure. I have seen them everywhere and they sell out all the time. This boot gives the loose fit look for the wide calf girls.
Sam Edelman | Woods Knee High Boot
Sold out last year but they are back and on sale! I’ve been eyeing these knee-high, wide-leg boots it’s that perfect mix of edge and elegance. These give everything from midi dresses to tailored trousers a sculptural lift.
Knee-High Boots
Flats
Effortless and versatile, flats are the go-to for days you want style without the heels. From classic ballet shapes to modern Mary Jane’s, these picks keep you polished and comfortable all season.
These are not your average ballet flats. The mirrored leather makes them feel elevated and cool, while the Mary Jane-style strap keeps them secure (and kind of adorable, honestly). I love that they slip on like mules but still feel polished enough to...
The Greta Ballet Flat Mule | Madewell
I’m obsessed with these dreamy Sézane Matilda ballerinas. The suede goatskin is soft and flexible so they break in instantly (hello, sockless comfort). A little pricy imo but potentially worth the investment if they hold up. Still doing some research...
Sezane | Matilda Low Ballerinas
I've been gravitating toward flats that feel sharp but effortless—and the Schutz Violetta Sculpt checks all the boxes. The pointed toe and subtle bow give just enough polish without looking stuffy, and the slingback strap makes them feel breezy and e...
SCHUTZ | Violetta Sculpt Ballet Flat
Now this will definitely be a shoe that I need to try before I buy. I have wider feet and I don’t love when you can see my “toe cleavage.” Although I’m sure they will be just fine in person. This will have to be a try on for sure.
H&M | Pointed Slingbacks
Leopard is going no where, so if you’re looking for a little pop of it in your outfit rotation these flats are the perfect addition. A more fun shoe but still practical and something that you will reach for again and again.
Naturalizer | Connie Mary Jane Slingback Flat
Sneakers/Tennis Shoes
Fall/winter sneakers bring the best of comfort and street style to cooler days. Think plush linings, neutral tones, and styles you can wear from coffee runs to casual nights out.
They are back and in so many colorways to choose from. These classic Puma Speedcat OG sneakers bring a sleek, retro vibe to any casual outfit. Lightweight and comfortable with a low profile, they’re perfect for everyday wear or adding a sporty edge t...
PUMA | Speedcat OG
Elevate your everyday sneaker game with the New Balance 9060—everything you want in a modern dad shoe but better. The iced coffee color is perfect and seems to be the “it” color for sneakers this fall and winter. Goes with everything and gives a more...
New Balance | 9060
Stunningly simple, effortlessly stylish. These are surprisingly on my wishlist. A little out of the ordinary for me but I think they would be a more practical fun pair of shoes for the colder months.
JW PEI | Caitlin Lace-up Ballerina Sneakers
The Adidas Tokyo strikes the perfect balance between retro charm and modern minimalism. The silver colorway is a show stopper if you are one for a standout shoe choice. I would personally be leaning towards a classic black and white I think but the s...
adidas | Tokyo Shoes
hese might just be the coolest shoes I’ve added to this list. The Speedcat OG Ballets feel like if a race car driver and a ballerina designed a sneaker together—in the best way. A little more adventurous than the Speedcat OG but either way you can't ...
PUMA | Speedcat OG Ballet Sneakers
The ultimate dad sneaker. I love the linen color way and the sea salt color way as well. They can definitely stand out with a monochrome outfit and a cute trench coat for the fall.
New Balance | 530 Sneakers