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These boots feel as good as they look.

collage of comfortable boots we recommend on a gradient blue background

Photo:Real Simple / Marcus Millán

Theyre not completely waterproof and are hard to slip on and off at first.

I thought I knew good boots until I finally bought myself a pair of Blundstone Originals.

I wear them with everything once the temperature drops, including jeans, skirts, and dresses.

Blundstone Originals High Top Boots

PHOTO: Blundstone

Once theyre on, though, youll be comfortable for hours.

Take note, though, that these boots are not completely waterproof.

Still, I cant recommend these boots enough, and theyre my go-to from autumn to spring.

Soda Jaber Boot

PHOTO: Amazon

Theyre made of vegan leather and arent as durable as pure leather boots.

The Soda Jaber Boots are a great value buy for anyone looking for comfortable heeled boots.

If youre not willing to splurge, these boots should be your first choice.

A person wears the Soda Jaber Boot

PHOTO: Real Simple

Theres a lot to love about the Callie Boots from Naturalizer.

Plus, they come in wide and extra-wide widths, making them much more accessible than other heeled boots.

These boots really stand out for their versatility.

A person walks outside while wearing the Soda Jaber Boot

They are not waterproof.

Theyre easier to break in, making them more comfortable from day one.

The memory-foam insoles provide comfort and extra support, while the rubber outsoles keep you steady on all surfaces.

A side view of the Soda Jaber Boot

Similar to other leather boots, they arent waterproof but are still highly durable.

Its only available in two colors and one width.

When it comes to riding boots, its best to stick with the pros.

A person wears the Soda Jaber Boot

Theyre only available in three shades of black.

The gabardine fabric fits almost like a sock, while the faux leather has more of a traditional appearance.

Unsurprisingly, these shoes are not water resistant, so theyre best for special occasions.

A person walks outside while wearing the Soda Jaber Boot

Theyre only available in one width.

If youre looking for a boot thats eye-catching yet casual, youll love the Red Wing Classic Mocs.

Similar to the Doc Martens Jadon III boots, theyre made with soft leather thats easier to break in.

A side view of the Soda Jaber Boot

The best part about the Mocs is the range of the color options.

There are 16 to choose from, so you might be tempted to buy more than one.

They dont have much insulation.

Naturalizer Callie Bootie

PHOTO: Amazon

Get them in one of three colors, and enjoy wearing them in any pop in of weather condition.

Theyre not designed for more rugged terrain.

Tallrain bootscan be hard to walk in, which is why we think a shorter boot is more comfortable.

Dr. Martens Jadon III Boot Pisa Leather Platforms

PHOTO: Dr. Martens

In addition, you’ve got the option to find the Chelsea boot style in wide andplushvariations.

There is a break-in period.

Merrell is a reliable brand for hiking boots, and the Moab 3 Mid Boot is a standout.

Thursday Women’s Combat Boot in Black Leather

PHOTO: Thursday

The mid-height ankle provides extra support, while the cushioned footbed has great shock absorption and comfort for miles.

The best thing about these boots is their versatility.

The Moab 3 design is also available in alower heightand in athermal style.

Ariat Sutton II Boot

PHOTO: Amazon

They arent designed for rugged terrain.

This material is incredibly durable, naturally water resistant (to a degree), and always in style.

Some boots are made with naturally softer leather to expedite that process, like theDr.

Aerosoles Centola Tall Boot

PHOTO: Amazon

Martens Jadon III Bootand theRed Wing Classic Moc Boot.

They age remarkably well, becoming even softer with time and developing an attractive patina.

Suede is another common material, as it has a stylish appearance.

Red Wing Heritage 6" Classic Moc

PHOTO: Zappos

Suede boots are best for special occasions and not for everyday use.

Foam insoles provide the most comfort because they can conform to your foot and provide excellent cushioning.

Ankle support is also important, especially if youre searching for hiking andwinter boots.

Columbia Women’s Moritza Shield Boot

PHOTO: Amazon

Good ankle support can improve balance and stability, improving overall comfort.

A well-fitting boot should feel snug but not tight, with room for the toes to wiggle.

Questions You Might Ask

How Much Should You Expect To Spend on High-Quality Boots?

Bogs Sweetpea II Waterproof Chelsea Boot

PHOTO: Zappos

What Are Some Brands That Specialize in Comfortable Boots?

Martens, andWolverine, all of which began as work boot brands and branched out into everyday wear.

Merrell Moab 3 Mid Waterproof Hiking Boots

PHOTO: REI

Ugg Adirondack III Boot

PHOTO: Nordstrom

A person wears a pair of UGG Adirondack III Boots outside on a pile of dry leaves

PHOTO: Real Simple

A person wears a pair of UGG Adirondack III Boots outside on a pile of dry leaves

A person walks outside while wearing the Soda Jaber Boot

Real Simple / Camryn Dilger