Fall is the season of transition and we’ve got some menswear inspired styles that are just as versatile as your go-to denim jacket. From Oxfords to raw leather booties, these bold classics can be worn throughout the season (and beyond) in a variety of ways.

And because they’re backed by the power of comfort, the only thing you have to worry about is where to go for happy hour after work or if the new brunch spot is worth checking out.

The Hester might be a bit of a tomboy but it’s got an adventurous soul. Pair with rolled and ripped boyfriend jeans and flannel accents or if you’re feeling a little more whimsical, an eyelet lace dress will do the trick.

The mix of leather and tweed make the Reegan an effortlessly chic style that defies limitations. Wear with some knee-high socks, skirts, and cardigans or rolled up distressed denim for a bit of edge.

The Matilda is a sleek silhouette with thrift store vibes and a penchant for indie band tees. Leather jackets, flowy dresses, dark wash skinnies, with boots that look this good there’s no end to what you can wear.