Get one step closer to finding a favorite (or two) with our style guide below.
The Best Winter Shoes For Men
The Lug Boot
Built for whichever direction the weather swings, the durable lug sole improves traction due to deep indentations and grippy texture (read: no slippin’ and slidin’), while an ankle length gives extra support as you trek up and down the street. Try them with straight-leg slacks for an out-of-office meets in-office look or your go-to jeans, cuffed to hit right at the top of the boots.
When a shoe comes from a long lineage of utilitarian use, the detailed craftsmanship, rooted in functionality, tends to carry over. Case in point: Sturdy materials, perforations (that used to drain water) and a sleek aesthetic make up the mix of brogues seen today. With something this well-made, you’re going to want to wear them every chance you get—dressed up, down and everything in between.
Everyone needs at least one everyday shoe that isn’t a sneaker. A timeless silhouette refreshed in an unexpected texture, like corduroy, fits the bill perfectly. Walking that fine line of smart and relaxed, your supreme comfort will remain a secret as you switch from denim to chinos to suit pants.
Sneaker culture is at the forefront of menswear with no signs of slowing down. Comfortable, cool factor and possibly a collectible—that’s a winning trifecta in our eyes. With endless colorway options, now’s your chance to bring the heat with darker, winter-ready hues and rich fabrics (we like suede) as you hit the pavement with a little more pep and style in your step.
The Chelsea Boot
If you’re on the hunt for a universally good-looking, slightly edgier shoe, this is it. A sleek shape in an easy, pull-on style with an even easier wearability factor means you can turn the most basic look up a notch. So, whether you’re wearing your favorite jeans-and-tee uniform or a skinny-fit suit, there’s a pair that will subtly or loudly complement whatever look you’re going for.
The Chukka Boot
There are many variants of this classic style but most have the recognizable characteristics: leather or suede, hits right at your ankle, only a few eyelets for laces and that ideal combo of elevated casual. You’ll get so much wear out of them: They play well with other pieces in your closet, feel good after you break them in (maybe even before, if you’re lucky) and successfully transcend trends.
The Best Fall Shoes for Men
A riff off of the desert boot, the Chukka hits the smart-casual sweet spot. The neutral shades work equally well with both jeans and chinos. For something a bit more adventurous, try a dark color or bold hue. Bad boy Steve McQueen wore Chukkas regularly. Nothing wrong with following in his footsteps.
The Hiker Boot
Taking a page from the more rugged hiking boot made for tackling trails, the hiker boot boasts soft leather uppers, cushioned soles and stylish stitching. In essence, an elevated version that pairs nicely with a more casual, outdoorsy outfit (think denim vest layered over a fleece hoodie). The mountain man look, minus the mountain.
The Brogue Boot
The perfect choice for the dapper chap, the Brogue was originally made in Scotland and Ireland in the late 19th century. Since then, the style has evolved from a farmer’s functional shoe (complete with holes to drain water when sloshing through wetlands) to a modern fashion staple. We love the plush suede, hip side zips, and decorative perforations. Take these to the street, the office, happy hour. Just skip the bog.
With athleisure wear front and center on the style stage these days, it’s hard not to give the sneaker a starring role. White canvas tennis shoes look sharp and work with just about any casual outfit, including skinny jeans and joggers. Whether you’re running laps or running for coffee, sneaks are your sole mate.
The Classic Oxford
When most men think “dress shoe,” it’s the Oxford that comes to mind. With its English pedigree and sleek silhouette, the Oxford is found more often in boardrooms than barrooms. However, this doesn’t mean you can’t wear it for a less formal occasion. We suggest sporting a casual pair of pants (dark-wash jeans or chinos) and a knit sweater to balance the dressier vibe.
The Weekend Loafer
Contrary to what the name suggests, these are not the lazy man’s go-to shoe. Loafers are simple slip-on shoes, designed without laces to trip you up. Ideal for loafing around town, around the house, even around a yacht if you’re so inclined (and don’t own a pair of boat shoes). Favored for their sturdy construction, clean, classic lines and Ivy League vibe, loafers pair easily with casual shorts, jeans and chinos. Socks or not? We say not.
Now swipe through to see how you can pair these shoes.
You’ve heard it before, “Shoes make the man.” Schedule a Fix to get your feet decked out in new kicks.