25 Comfortable Boots That Will Get You Through the Entire Season

Head Held Hike Lace-Up Boots ($69) would look cute with thick wool socks poking out from the top.

This UO Margot Suede Boot ($79) has a block heel that makes it comfortable to walk in.

This classic Steve Madden Brave Bootie ($110) will never go out of style.

If you're looking for an everyday shoe, this Vagabond Marja Chelsea Boot ($175) is an excellent choice.

The side zipper detail on this Naturalizer Jinnie Tall Boot ($150, originally $200) makes it easy to take off.

We love the detail on this River Island Wide Fit Buckle Boot ($84).

We love the leopard haircalf print and texture of the Nora ($225) boot.

The Duck, Duck, Boot in Navy ($99) is your go-to for rainy-day school drop-offs.

Omgard Ankle Rain Boots ($16-$18) are waterproof shoes with a superglittery finish.

Take on cold weather in style with The Fix Mika Boots ($139). The bulky shearling will contrast well against a pair of skinny jeans.

The great thing about the cowboy-inspired Flattered Rebecca White Snake ($349) boot is that it's really an everyday shoe — the heel is low enough that you can spend hours in them.

Wear this stylish Sam Edelman Penny Boot ($150) every day.

Dr. Martens 1460 Smooth Boots ($140) are not just for the kids. You can totally wear a pair. Just dress them up with black jeans and a blazer on top.

Engineering Ensembles d'Orsay Booties in Mustard ($55) come in two shades.

These J. Adams Low-Heel Ankle Boots ($18-$40) come in every color you could think of.

Want something fashion-forward? Try a sock-like boot this season — this metallic Loeffler Randall Carter Knit Boot ($395) is a comfy choice.

Take a walk on the wild side in these Sam Edelman Kinzey Pointy-Toe Booties ($160). You can wear these with something as simple as jeans and a t-shirt.

White is a hot color for Fall, so try these Nine West Leva Leather Ankle Boots ($60).

The Sam Edelman Tinsley Rain Boot ($55) is so adorable, we'll even wear it when the weather is nice.

Work the Zara Embroidered Leather Cowboy Ankle Boots ($169) with your darkest denim.

Wear the London Rebel Kitten Heel Point Boot ($36, originally $73) with cropped denim.

We used to think it was impossible to find a good-looking rain boot, but then we stumbled upon these Jeffrey Campbell Stormy Rain Boots ($44, originally $55).

These faux-croc boots are a great day-to-night shoe. Try the Bella Vita Everst II Pointy Toe Booties ($80) with black jeans or a dress.

If you're in the market for a trendy boot, look no further. These Loeffler Randall Isla Chunky Heel Slim Ankle Booties ($450) have a pointy toe, a chunky heel, and a sock-like fit at the ankle. We're adding these to our wardrobe stat.

The wooden heel breaks up the darkness of these J. Adams High-Heel Buckle Ankle Boots ($37).