It's officially boot season, baby! Whether you're a fan of cold weather or not, there's no denying that this footwear is one of the hardest-working items in our closets (next to our coats). Every winter wardrobe is incomplete without a pair of good boots, so of course, we've been spending all our time thinking about them lately—can you blame us? But we'll be the first to admit that while it's fun to think about footwear, frankly, it can be hard to determine what boots are worth buying. Even more so when you consider the plethora of current boot trends—from animal print to sumptuous suede—that make it nearly impossible to pick an option for the season. Luckily for us, there's one time-honored classic that can help cancel out the noise: Chelsea boots.
With so many options on the market, sometimes the "simplest" styles are the best investment for the season. That's especially true when it comes to Chelsea boots, which have managed to remain relevant over the last century. One reason the allure of these boots has remained intact is due to the androgynous silhouette that's ideal for winter rain and snowstorms—i.e., the style features a flat sole, round toe, and ankle-length shaft that's typically made from waterproof leather. But beyond the functionality, what's made this "simple" boot a must-have style season after season is how it's continuously evolved in runway collections. In recent years, you can find versions of this classic footwear with cool twists, such as iterations with pointed toes, knee-high lengths, and even chunky lug soles.
To get the full story, I talked to fashion industry vet Lindsay Weiss, who’s been wearing the Khaite Colt Boots nonstop. She swears by Chelsea boots in general, but this specific pair stands out among the rest. The combination of the sculptural toe, polished leather, and hardware-free design makes them feel elevated in that quiet, intentional way that defines modern winter dressing. Below, Weiss shares exactly why she chose them and how she styles them. Plus I'm sharing the other Chelsea boots I’d recommend if you’re currently in the market.
A Fashion Insider's Take
What made you choose the Khaite Colt Boots, and what stood out most when you tried them on?
I loved the Colt style from over the summer but held out for the boot version. The toe is just so unique and special looking—different than your average flat boot. I also am obsessed with the shiny leather that isn’t patent. Just a little polished looking. And they’re SO comfy!!! Oh, there’s also no hardware, which I appreciate so any bag goes. I’m a stickler for matching my hardware, so this is bonus points for me!
What do you personally love about Chelsea boots as a style?
I love how they’re flat, and I can walk all over the city in them. I don’t want to wear sneakers all the time, but these feel as comfy.
How do you typically style them for everyday wear?
I love the juxtaposition of wearing them with even a T-shirt to make the look feel elevated. This fall, I’ve been wearing them with one of my leather jackets, especially my new navy Khaite one. I love navy and black together!
Shop Weiss's boots:
Chelsea-Boot Styling Tips
Tip #1: Style Them With Staples
WEAR: Trench Coat + Button-Down Shirt + Tank Top + Miniskirt + Crossbody Bag + Chelsea Boots
Styling Notes: When in doubt, you can't go wrong wearing this boot style with other classic staples—e.g., a trench coat, button-down shirt, tank top, miniskirt, and crossbody bag. It's a timeless formula that always looks good.
Tip #2: Show Off Your Boots
WEAR: Long Coat + Striped Sweater + Shorts + Knee-High Chelsea Boots + Tote Bag
Styling Notes: If you want to take a risk with your ensemble, consider putting your Chelsea boots front and center. You can draw attention to your boots by styling them with pleated shorts (or a miniskirt). Just be sure to pair your shoes and shorts with other cold weather friendly items to make them look practical.
Tip #3: Style Them With Cropped Denim
WEAR: Long Coat + Black Sweater + Cropped Denim + Chelsea Boots + Clutch
Styling Notes: Another straightforward way to make these boots stand out? Style them with straight-leg cropped jeans, a sweater, and a long coat. It will give you a chance to show them off without showing skin.
Tip #4: Opt for a Taller Silhouette
WEAR: Turtleneck Sweater + Miniskirt + Knee-High Chelsea Boots + Shoulder Bag
Styling Notes: Another way to make this "simple" shoe style stand out is to opt for a pair that is a bit taller. By opting for a pair of knee-high Chelsea boots, you'll ensure these boots are the focal point of your outfit.
Tip #5: Style Them With a Dress
WEAR: Sunglasses + Maxi Sweaterdress + Chelsea Boots + Shoulder Bag
Styling Notes: One of the hardest things about styling Chelsea boots is figuring out what type of pants will pair well with them (no matter the height). Rather than trying to find the perfect hemline length, try wearing a dress with boots. It's a simple solution that will save you time and keep you looking stylish all winter.
Tip #6: Embrace Double Denim
WEAR: Turtleneck + Jean Jacket + Belt + Denim + Chelsea Ankle Boots + Clutch
Styling Notes: When it's far too cold to wear a dress but you can't be bothered to put much thought into what you're wearing, it's best to keep it simple. Pairing your Chelsea boots with a double-denim outfit can make it look like you put a considerable amount of effort into getting ready (without that actually being the case).
Tip #7: Play With Textures
WEAR: Shearling Coat + Sweater + Leather Trousers + Chelsea Ankle Boots
Styling Notes: When you feel inspired to get more creative with your winter outfits, consider incorporating different textures to make your Chelsea boots feel brand-new. There's no better way to make the black boots in the back of your closet feel bolder than by styling them with leather trousers, a sweater, and a shearling jacket.
Tip #8: Go Monochrome (Except for the Boots)
WEAR: Leather Coat + Crewneck Sweater + Trousers + Suede Chelsea Boots
Styling Notes: You don't have to develop groundbreaking styling formulas for this boot to feel brand-new (see above as proof). You can make your Chelsea boots stand out by embracing an almost head-to-toe monochrome. The pop of color in the form of boots will make any all-black outfit feel fresh.
Tip #9: Embrace Edgier Styling
WEAR: Leather Moto Jacket + Slip Dress + Chelsea Ankle Boots
Styling Notes: Beyond playing with colors or texture, there are other ways you can make your Chelsea boots feel cooler—case in point: the outfit above. Pair this polished shoe style with a slip dress and moto jacket to give it a bit more edge.
Tip #10: Coordinate Your Accessories
WEAR: Baseball Cap + Long Coat + Jumper + Skinny Jeans + Chelsea Boot + Handbag
Styling Notes: In addition to pairing your boots with unexpected pieces, you can also make them stand out by coordinating them with your accessories. Take a cue from the outfit above by matching the color of your shoes with a baseball cap (or bag) to make your winter outfits 10 times chicer.
Tip #11: Embrace Chelsea Boots With Heels
WEAR: Sunglasses + Oversize Blazer + Cardigan + T-Shirt + Skinny Jeans + Chelsea Boots + Tote Bag
Styling Notes: One way to elevate this boot this winter is to opt for a heel version (excuse the pun). Even the most "basic" outfit formula—e.g., an oversize blazer, T-shirt, and skinny jeans—can feel bougier with the addition of a heeled Chelsea boot.
Tip #12: Play With Prints
WEAR: Leather Blazer + Sweater + Leopard-Print Pants + Colorful Chelsea Boots + Mini Bag
Styling Notes: Hopefully by now, you've got a good grasp on how to style a Chelsea boot in a way that reflects your personal style. However, if we can give you one last nugget of wisdom, let it be the following: Get playful. Ultimately, the beauty of this boot style is that it's a cult classic; therefore, they can go with almost anything. Don't be afraid to style it with trendy prints or colors because they'll always look good, no matter how you choose to wear them.
Shop More Chelsea Boots
Reformation shoes are elite.
If I were on the hunt for a new pair of Chelsea boots, these would be in my cart.
The suede is really a winner.
Functional and chic.
How cool are these?
A designer deal you’ll brag to your friends about.
We needed to show off a fun colorway.
It’s the buckle for me.
I’m enamored.
These are just a bit chicer than the rest.
This burgundy moment is killer.
Now this is stunning.
You must try them out in suede.
It’s the teeny-tiny heel for me.
This with a good pair of socks.
I can confirm these boots are warm.
Sorel might as well be the captain of the Chelsea-boot ship.
