Best Foot Forward: 3 Must-Have Shoe Styles for Fall

You can wear anything as long as you put a nice pair of shoes with it.
— Taylor Momsen

Shoes are one of the most exciting categories in men’s fall fashion. A great pair completes your outfit and makes you feel like you can take on the world. There’s power and magic in a kick-ass pair of kicks, which, as you know, everyone notices – especially women (ergo the dating tip: wear crappy shoes on a first date – or any date – at your peril). 

With so many gorgeous options to choose from this season, here are three must-have shoe styles that will step up your game, wherever you go. In order from casual to formal:


Unless you’ve been living in a cave the past few years, one thing you probably noticed is that sneakers are everywhere. The sneaker-as-fashion-footwear movement started sprouting in a big way several seasons ago, and now it’s mushroomed into a full-blown sneaker-as-THE-fashion-footwear phenomenon.

Clockwise from Left: Tom Ford, Valentino, Diesel

Clockwise from Left: Tom Ford, Valentino, Diesel

There are sneakers now in every permutation and transmutation imaginable, at every price point, from household names like Converse and Vans to pretty much any high-end designer brands you can name.

What sealed the deal for the sneaker’s ascent to the fashion footwear throne happened when top menswear tastemaker and designer, Mr. “I have resisted the tennis shoe” Tom Ford, finally succumbed to the force of the sneaks and launched his own ultra luxe sneaker line this season with materials and craftsmanship on par with exclusive handcrafted dress shoes:

Each shoe is manufactured in Italian workshops by artisan cobblers who spend a week stitching, polishing and then ‘resting’ the leather for 10 days where the shape of the shoe is created. They’re then hand-polished over three days.
— Tom Ford

Unless you work at a super conservative work environment, you can pretty much rock a pair of sneakers with any outfit, including your suit… or at least with your office wear on Fridays. Dress up your casual outfit or tastefully dress down your more dressy looks with leather sneakers in a simple design and rich color. Or swing the other way and make the shoe pop with an eye-catching design, unexpected materials, bold colors, or all three combined.

This is the year of the elevated sneaker. It’s comfortable, sporty, vastly versatile, and a fresh way to enliven any look.

Chelsea Boots

The Chelsea boot is perfect marriage between simplicity and attitude, with a British heritage and a rock and roll sensibility.

Clockwise from Left: Charles Tyrwhitt, A.P.C., Frye

Clockwise from Left: Charles Tyrwhitt, A.P.C., Frye

With Victorian roots, the boots got their current name and initial fame in the mid ‘50s after a group of young artists, musicians, film makers, and fashion types from west London dubbed the ’Chelsea Set’ started wearing them. Their popularity soared in the ‘60s when a variation of the boot with a pointed toe and more pronounced Cuban heel was worn by The Beatles and eventually became known as the ‘Beatle Boot.’

Favored by Mods and other famous rock bands like The Rolling Stones during the same era, the Chelsea boot is now forever associated with the Beat/Mod generation’s countercultural aesthetic, and continues to be preferred by rock and roll types or any man who wants a stylish way to stand apart from convention.

Perfect for an edgy yet polished look for both work and off-duty, Chelsea boots come in various materials, finishes, and styles to fit your taste and lifestyle. The rounded toe is more casual, as the narrower toe is more formal. Smooth shiny leather lends a sleekness while suede or textured/distressed leather gives off a more casual and rugged look.

What’s great about the Chelsea boot is the elastic strip that lets you slip it on and off with ease, and the narrow ankle fits smoothly under slim pants for a very streamlined look with a good dose of attitude. Wear them with suits for a sophisticated statement away from conventional dress shoes, or with jeans for a minimalist, refined masculinity.

The Chelsea boot is a classic that you’ll wear forever. Slip these on and up your cool.

Monk Straps

As more and more men have been obsessing over more expression to dressing up, the monk straps have been creeping up everywhere, in all kinds of materials, designs and in an explosion of colors. If all you have are lace-ups and loafers, do yourself a service and join the order of the monks.

Clockwise from Left: To Boot New York, Salvatore Ferragamo, Alexander McQueen

Clockwise from Left: To Boot New York, Salvatore Ferragamo, Alexander McQueen

Originally made and worn by European monks centuries ago as a more protective and durable alternative to sandals, these buckled beauties make bold style statements that betray their conservative provenance. 

A lot of guys shy away from the monk because they don’t think they can pull it off. They either think they’re too fancy or simply don’t know what to wear with them. The surprising thing about monk straps are that they, like the other styles mentioned above, are quite versatile.

Polished, more refined versions are perfect to pair with a suit or dress trousers, but can also dress up a pair of jeans or chinos. By the same principle, dress down a more buttoned-up outfit with a suede pair, or wear them with casual duds as an unexpected and elegant update to your typical everyday shoes.


Monk straps come in single, double, and even triple straps, and the variety should appeal to just about every personality. The lone strap, while quieter, still packs flair. The double strap is the most popular, and for good reason due to its banging style impact. Triple straps look best on boots and offers a sick edge that’s both too cool yet never rude.

Monks are meant to be noticed. They’re all about expressing your personality and is a bit of a show-off, but in a good way. They exude a worldly, European elegance and just the right touch of masculine vanity without being flashy. And because this shoe is meant to be seen, be sure to hem your pants with little to no break so that the entire shoe is exposed for all to admire.

The monk strap is the ultimate footwear style statement. Step into a pair, announce yourself to the world, and be handsomely rewarded. 

And now a question for you: Which shoe style are you eyeing this fall?