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It’s prime boot-buying season. The temperature is chilly, the weather is unpredictable, and your rotation of outfits is heavy on rich textures. Even when perusing affordable shopping destinations like Zara and H&M, boots tend to fall on the more expensive side of the price spectrum, so any pair you bring home will be an investment meant to hold up for more than a single season and work with dressy and casual looks. 

To me, the best boots fall into a few key categories, and I always try to make sure I have at least one of each in my rotation any given season. First, there are the practical everyday boots. Think equestrian-inspired or moto styles. These are sturdy, comfortable, and able to handle my daily commute on the subway. Next up, there are party boots. These are styles with a higher heel pitch and may come in unexpected colors or materials, such as horsehair or silver leather. Next, there are the cozies. This category includes Uggs, hiking boots, and rubber rain galoshes. Lastly, there are booties, which I consider the most versatile option of the bunch. 

Once I have each of these categories squared away, I’m a little more open to my whims, perhaps picking up a trendy style for the season ahead or opting for a beloved silhouette in a fun new color or material. Ahead, I’ve collected 31 of my current favorites to help you kick-start your lineup of cute boots.

Steve Madden Baily Knee High Platform Boot

Steve Madden

Baily Knee High Platform Boot

$50

Platform boots that are made to stand out.

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Mango Platform Track-Sole Ankle Boots

Mango

Platform Track-Sole Ankle Boots

$100

Walk comfortably in these chic boots.

Ganni Western Leather Ankle Boots

Ganni

Western Leather Ankle Boots

$430

A subtle way to lean into the Western trend.

Loeffler Randall Elise Leather Ankle Boots

Loeffler Randall

Elise Leather Ankle Boots

$351

Sleek ankle boots to try pairing with your work trousers.

Souliers Martinez Chueca 90 Suede Platform Boots

Souliers Martinez

Chueca 90 Suede Platform Boots

$480

You’ll be the life of the party in these platform boots.

Reformation Remington Ankle Boot

Reformation

Remington Ankle Boot

$348

Break out these boots for inside activities or days when the weather will allow. 

Dr. Martens Jadon Platform Boot

Dr. Martens

Jadon Platform Boot

$210

Once you break these in, you’ll never want to take them off.

Jeffrey Campbell Geist Square Toe Boot

Jeffrey Campbell

Geist Square Toe Boot

$175

I’m getting a retro vibe from these, and I’m into it.

Zara Gaitor Boots

Zara

Gaitor Boots

$90

These aren’t your average boots. They’re modern and trendy.

Aeyde Zoe Ankle Boots

Aeyde

Zoe Ankle Boots

$495

Suede may be harder to take care of, but this pair is worth that extra effort.

Schutz Maryana Pointed Toe Block Heel Knee High Boot

Schutz

Maryana Pointed Toe Block Heel Knee High Boot

$258

Bold boots are in, and this pair is an outfit game changer.

Cole Haan Hampshire Waterproof Riding Boot

Cole Haan

Hampshire Waterproof Riding Boot

$300

Embrace your equestrian style with a pair of riding boots.

Mango Leather Boots With Kitten Heels

Mango

Leather Boots With Kitten Heels

$140

These will add a pop of fun to any outfit.

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H&M Warm-Lined Boots

H&M

Warm-Lined Boots

$65

Cozy meets chic.

Jeffrey Campbell Moto Boots

Jeffrey Campbell

Moto Boots

$298

These chunky boots add edge, no motorcycle required.

Ugg Classic Mini II Boots

Ugg

Classic Mini II Boots

$150

If your size is still left in stock, consider yourself lucky.

J.Crew Piper Ankle Boots

J.Crew

Piper Ankle Boots

$298
$241

These sleek boots add a subtle touch of texture to your style.

Everlane The City Boot

Everlane

The City Boot

$275

These suede boots are a soft, slick style for a casual city look.

Madewell The Dimes Boot

Madewell

The Dimes Boot

$210
$137

Texture and print combine to create boots that turn heads.

By Far Este Leather Ankle Boots

By Far

Este Leather Ankle Boots

$540

White boots will always be in style.

Schutz Maryana Block Boots

Schutz

Maryana Block Boots

$238

I never found heeled boots comfortable till I was introduced to Schutz.

H&M Ankle-High Leather Boots

H&M

Ankle-High Leather Boots

$199

The ankle strap makes all the difference for these sleek boots.

Adidas by Stella McCartney Terrex Rubber Hiking Boots

Adidas by Stella McCartney

Terrex Rubber Hiking Boots

$223

For days with bad weather, these boots are just the thing.

Franco Sarto Giselle Knee High Boot

Franco Sarto

Giselle Knee High Boot

$215

Sleek boots are a wardrobe essential.

Zara Ankle Boots

Zara

Ankle Boots

$70
$30

Break these boots out for nights on the dance floor.

Ugg x Telfar Logo-Cutout Leather Ankle Boots

Ugg x Telfar

Logo-Cutout Leather Ankle Boots

$220

Comfort meets cool with these collaborative boots.

Rag & Bone Rover Booties

Rag & Bone

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Rover Booties

$395

I love the subtle style of these boots.

Sorel Brex Heel Leather and Mesh Ankle Boots

Sorel

Brex Heel Leather and Mesh Ankle Boots

$200

Weatherproof but still a style statement.

Larroude Mini Kate Boots

Larroude

Mini Kate Boots

$430

Everyone needs a sleek pair of simple white booties.

& Other Stories Leather Sock Boots

& Other Stories

Leather Sock Boots

$199

These boots look so expensive.

Intentionally Blank Passage Boots

Intentionally Blank

Passage Boots

$269

A stacked heel is a dressy touch.

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