The only thing better than transitioning to sweater weather is when it's finally time to change shoes, swapping out sandals and sneakers for boots. One or two pairs could suffice, especially if you don't live in a place where snow is a concern. But in my experience, it takes at least three styles of boots to get through winter and fall in style.
Chelsea boots top the list as an essential wardrobe staple because they go with everything, are easy to walk in, and look totally timeless. Invest in a well-made pair, and keep them looking pristine with shoe polish, waterproofing, and regular sole maintenance, and they'll last for seasons to come.
Next are flat, lace-up ankle boots. These run the gamut from sturdy snow shoes to cool combat boots and can be found in an array of materials from leather to nylon. Opt for a chunky sole, or look for a combat-boot style with buckles and embellishments. It's a subtle statement shoe no matter how you wear it.
Finally, the prettiest boots in our closets are often knee-high heeled boots. They're not always practical but are guaranteed to take any outfit to the next level. Choose a stacked heel for maximum comfort, or try out a short heel in stunning suede to wear with a mini or midi skirt. And don't forget boot inserts or hangers to help the tall shaft keep its shape while in storage.
Ready to complete your capsule wardrobe with a new pair just in time for the holidays? We've pulled several versions of each style that demonstrate the versatility within each category. The only hard part is choosing which new boots to break in first.
1. Knee-High Heeled Boots
Brown boots are underrated; they go with everything and look even more luxe than black.
These smart, short-heeled suede boots are on the top of my wish list.
This boot comes in so many super colors and materials it'll be hard to choose just one pair.
Knee-high boots with Western vibes or prints work, too.
For a wear-everywhere boot, look for a pair with a sturdy, stacked heel and a wide shaft so you can wear them with a number of outfits.
2. Flat Lace-Up Ankle Boots
Jadons are a perennialBest Knockoff Luxury Clothing favorite, particularly for the NYC-based editors.
You can't go wrong with a classic pair of black lace-up combat boots.
Weatherproof style isn't too much to ask for. See?
A smart side zipper means that you don't have to fuss with the laces or buckle to get these beauties on and off.
Did someone say après-ski? Remember: Winter boots don't have to be boring; look for something with a pop of color that will stand out.
3. Chelsea Boots
When choosing a pair of Chelsea boots, try on styles with different treads and shaft heights so you know what works best for your feet.
If jeans and boots are your uniform, then you'll want to add a pair of ankle-high Chelsea boots to your closet ASAP.
If you're going for genuine leather, look for a higher lug sole to help keep 'em dry.
Suede can be challenging to take care of, but when the boots are this pretty, it's worth the effort.
Chelsea boots come in a variety of materials and heel heights—we love the slightly curved look of this pretty pair.
Another classic pair of Dr. Martens that will always have a place in my closet.
-
5 Street Style Trends from Milan Fashion Week That Will Be Everywhere This FallThe go-to It items.
-
Giorgio Armani's 50th—and Final—Collection Paid Homage to the Late Designer's LegacyEighties supermodels, core house codes, and plenty of Armani gray were the capstone to a half-century of the iconic Italian house.
-
5 Street Style Trends from Milan Fashion Week That Will Be Everywhere This Fall
The go-to It items.
-
Everyone in Paris Just Ditched Ankle Boots for This Boot Style That's Way More ElegantAnd super sleek.
-
J.Crew Just Partnered With the Luxury Afrofuturist Jewelry Brand You Should Know About—6 Gorgeous Pieces From the Capsule CollectionAn elegant collaboration with Khiry's Jameel Mohammed.
-
*Not* Suede Boots: The Rich-Looking Boot Trend Fashion People Everywhere Are Wearing With Jeans and Skirts for Fall 2025You'll want to add a pair to your rotation.
-
Cool-Girl Fall Era Loading—31 Picks From Zara, J.Crew, and Gap That Fit the BillI'm a senior shopping editor and these have my stamp of approval.
-
*Not* Ankle Boots—The Rich-Looking Shoe Trend That’s Quietly Taking Over for Fall 2025Shop the style inside.
-
Reformation Just Launched a Collaboration With Nara Smith, and It's a Vintage-Inspired DaydreamExpertly crafted from scratch.
-
I'm the Creative Director at J.Crew—These Are the New Fall Items I Tell Everyone to BuyOlympia Gayot's favorites.
