Blog

Who wouldn’t love a season when it’s cool enough to finally wear boots, but not so slushy that you need bulky snowshoes? As the leaves turn, consider these ways to keep your feet dry and your fashion quotient high: 

The chukka 

Also known as the desert boot, this one has an illustrious history as one of the smarter forms of casual—but not toocasual—footwear. The late actor Steve McQueen favored chukkas, and we know he rarely took a false sartorial step. Wear them in darker tones, like this pair from Tod’s, or feel free to get adventurous with bolder colors. 

The Chelsea 

Speaking of ’60s icons, four upstart lads from Liverpool transformed this boot into an iconic fashion statement almost overnight, and it’s no less popular today. A good pair of Chelseas splits the difference between summer and fall, as well as between formal and informal, proving versatile and effortlessly stylish. 

The lace-up 

If you want a bit of edge, but feel the Chelsea is just too rock, the perfect alternative is a black leather lace-up. It’s got a bit of a punk vibe, but is much dressier than a combat boot. And it can be worn with a far wider range of outfits. Dress it up with a suit or down with a pair of faded black jeans. Or, if you’re feeling a little bolder, white jeans. 

The combat 

Determined to be less conservative still? Go all out with a classic pair of British combat boots. Thanks to the ’90s nostalgia that’s all over fashion right now, this silhouette is having a serious moment.  

The brogue  

Brogue boots offer an ideal transition from your summer shoes to something more appropriate for the weather. The right pair will look like your ordinary brogues, only taller.