As we transition out of sneaker and loafer season, it’s time to start thinking about the boots you have in rotation. Sometimes all you need is one good pair, other times it’s nice to have a few different pairs for different occasions. To help you on your footwear journey, we’ve gone ahead and rounded up a list of both classics and fancier options.

Ask yourself: will I be bracing the snow the next few months? Or are you one of those Californians who only experiences winter in theory? Do you prefer biker-chic, or Dapper Dan? Whatever your needs may be, we have the boot for you.

Timberland Men’s 6-Inch Boots In Black ($198)

We’re starting off the list with an absolute classic. Timberlands are known world wide, but are certain to pop up in the colder New York City months. If you want to go a bit alternative, you can opt to get them in this all black style, rather than their iconic yellow hue.

Belstaff Trialmaster Leather Boot ($395)

This one’s for the bikers, or the wannabe bikers more specifically. And there’s no shame in that. These boots, debuting in the 50s, are a tough look based on British military styles. Take ’em for a ride.

Dr. Martens Vegan 1460 Lace Up Boots ($150)

If you prefer a non-leather shoe, this is the one for you (although the same style is available in leather). These cherry colored boots are made to worn in and worn out. As the surface is rubbed down, it will reveal an even brighter shade of red underneath. That way they only get better with love.

Grenson Fred ($450)

For the dapper man, this hand-painted leather boot is the perfect finish to a formal outfit, or to dress up a casual look. Though it may not be the most durable on the list, what it lacks in ruggedness it makes up for in class.

YSL Army Chelsea In Smooth Leather ($995)

Double Dapper. This YSL boot is the epitome of the fancy man’s chelsea. It’s patent leather finish makes it a standout, in the good kind of way. Tuck it under a dress pant, or roll up a pair of jeans to let it shine.

Thom Browne Black Nylon All Terrain Boot ($1050)

Once again moving away from leather, this nylon number is the high fashion response to the winter boots your mom made you wear as a child. With classic red, white, and blue Thom Browne accents, the structural elements and easy silhouette stand out.

Diesel D-Throuper DBB ($248)

Get the military look, minus the service, if that’s your thing. These pre-worn boots won’t require any breaking in (aesthetically) and feature a combo suede and canvas upper.

Gucci Ankle Boot With Buckles ($1450)

On the other end of the spectrum are these Gucci ankle boots with three ornamental buckles. The mixture of soft leather and gold detailing just feels  oh-so-luxurious.

 

Fluevog x Viberg Racer Boot ($700)

This must-have boot of the season incorporates a new collaboration between two long-standing, west coast family-owned shoemakers. The standout boot also donates a portion of the sale directly to the British Columbia Parks Foundation.

Patagonia Wild Idea Work Boot ($399)

Patagonia is known for having a more than superficial commitment to the environment. In that spirit, they decided to use bison hides traditionally thrown away to craft these gorgeous work boots. The soles are also made with a blend of recycled materials.

Eddie Bower K-6 Boot ($120)

A little bit kitschy and a little bit just plain cute, these Eddie Bauer boots have been around since the 60s. Now that everyone seems to be going gaga for hiking boots (even Gucci has a pair), why not go straight to the source? Being the blueprint is always in style.