Calvin Klein

Dameon Lace-Up Boot

nordstrom.com

$165.00

SHOP

Add a little edge to your suit with a strategic red stripe. Plus, the sturdy construction will keep the elements at bay. Courtesy

Thursday Boot Co.

Captain Boot

thursdayboots.com

$199.00

SHOP

A combat-style boot is great for winter-dress it up with a suit during the week, and feel free to wear it with jeans on the weekend. Courtesy

Allsaints

Perch Boot

us.allsaints.com

$248.00

SHOP

Allsaints boots nail the balance of dressed up but un-stuffy. These work as well with a suit as they do with everything else in your wardrobe. Courtesy

To Boot New York

Andreas Chelsea Boot

nordstrom.com

$237.90

SHOP

These with a navy suit-no fail. Courtesy

Cole Haan

Wagner Grand Cap-Toe Waterproof Boot

nordstrom.com

$320.00

SHOP

Polished and put-together enough for any suited-and-booted look. Plus: water-resistant leather.Courtesy

Hugo Boss

Cardiff Leather Chelsea Boot

mrporter.com

$400.00

SHOP

For the guy who won't let winter stop him from wearing Chelsea boots.Courtesy

Red Wing

Williston Plain-Toe Boot

nordstrom.com

$430.00

SHOP

Perfect if you want something that's in the vein of a work boot, but still pairs nicely with your rugged tweed and flannel tailoring.Courtesy

R.M.Williams

Suede Chelsea Boot

mrporter.com

$495.00

SHOP

Suede might not be the thing for your next big meeting, but it'll look great with a casual suit with a good bit of texture.Courtesy

Allen Edmonds

Rafael Chukka Boot

nordstrom.com

$545.00

SHOP

If you're not sure where to start, you can rarely go wrong with a chukka boot. Courtesy

Common Projects

Leather Chelsea Boot

mrporter.com

$620.00

SHOP

When you need something with a hardcore sole-and that can be easily paired with pretty much any suit in your wardrobe.Courtesy

AMI

Suede Jodhpur Boot

mrporter.com

$630.00

SHOP

For the guy with very good taste in boots. Courtesy

Saint Laurent

Wyatt Chelsea Boot

nordstrom.com

$995.00

SHOP

This is an advanced move, but it's tough to beat a Saint Laurent Chelsea boot. Courtesy

Berluti

Shearling-Lined Leather Boot

mrporter.com

$2780.00

SHOP

These boots will last you a lifetime. They're also shearling-lined for warmth. Courtesy