You’ve got to love boot season. Both fashionable and comfortable, boots are the favorite choice in leather shoes for guys everywhere. Just like boots, you’re probably breaking out the denim quite a lot around this time of year. Both fashionable and comfortable… wait, we’ve been here before.

Jeans and boots go together like scotch and cigars, but if you want ideas on new ways to pair the two classics, we’ve got some suggestions. Click on the subheads for visuals created through Polyvore.

Vintage Levi’s + The Dean Chelsea Boot in Marrone

Every guy I know, and every girl for that matter, has a pair of their favorite Levi’s in their closet. These Levi’s in particular stand out to us because they have been preserved since 1962. And yet at a cursory glance they could be mistaken for a modern pair. The opposite is true for The Dean Chelsea Boot in Marrone. Though they were handcrafted in Italy this year, you could have easily seen a pair just like them donned by a 1960s Mod. Fashion is kind of cyclical like that.

Grey wash jeans + The Newman Chukka Boot in Marrone

An unlikely color combo, the faded greys of the jeans contrast vividly with our Newman Chukka Boot in Marrone. Since you’re pairing neutral on neutral, the options for building this look out are limitless. We like it with a plain white tee and an oversized black parka for the chill.

Tapered black jeans + The Dean Chelsea Boot in Oxblood

The tapered ankle of these jeans allow for an easy fit into the Dean Chelsea Boot in Oxblood, but they still have a loose enough fit to not be deemed “skinnies”. The dark black wash of the jeans feeds into the elastic detail, creating an elongating effect to the legs… something you don’t get so much of in men’s shoes. And since the rich, oxblood leather goes great with anything; you’re able to dress them up or down as you wish.