Boots are a staple. Dressed up or dressed down, there’s something about a boot that feels a little more put together and prepared than, say, a sneaker. And that goes for the best boots for fall, winter, spring, or, yes, even summer. That said, there are a lot of options out there. To narrow it down, you need to consider four main factors: style, quality, comfort, and utility.
These are the four main boot styles that every guy should own to get through just about any situation you could find yourself in.
The Chelsea Boot
The defining footwear of art history majors and the 1960s London scene, the Chelsea boot is one that refuses to go out of style. Case in point: The Beatles helped popularize them in the band’s heyday and the style remains popular to this day. The ankle-high boots tuck just right at the break of a skinny jean or trouser and gives your outfit an overall edge. Because of the close-fitting design, it’s best to not go with anything wider than a tapered leg here to keep the lines sleek to elongate the overall appearance of your inseam.
As classic as it gets, the Velasca Magut is a calfskin Chelsea at a reasonable price for an Italian shoe. Keeping the traditional silhouette, the Magut is slightly modified for the modern wearer with a more rounded toe and an elegant ankle cuff that tucks nicely into a pair of Levi’s 511s.
Thursday Boot Co. Cavalier Chelsea Boot
This is the perfect boot for dressing up, dressing down, and just getting out of the house for some errands. For less than $200, you’re looking at a handcrafted suede boot that can be worn throughout the colder months and hold up to the elements with proper care (it is suede, after all) for years to come.
Beckett Simonon Bolton Chelsea Boot
248 five-star reviews can’t be wrong about this one. The bordeaux-red leather of the Bolton is eye-catching without being ostentatious. It’s a boot you can pair with a corduroy suit and look just as good as if you were wearing any other dress shoe.
The Chukka (Also Called Desert) Boot
Another ankle-high option, this boot is like the cousin with a rugged history to the more posh Chelsea. The slope of the boot’s laced upper leads to an elongated toe. The style has roots in a type of military shoe that was worn by British soldiers during the North African campaign in World War II (hence the desert boot nickname). Today, chukka boots are the perfect casual everyday boot for year-round wear.
Clarks Desert Boot
The best in the game for a chukka boot is Clarks. Known for simple design and rugged styling, the Clarks desert boot is one of the easiest shoes to pair with a dark jean and a comfortable sweater. Any of the suede colorways work phenomenally well to dress up or down, but I’m partial to Ginger Hairy Suede, both because it’s a fun name and for having a rich tonal hue to it.
Marc Fisher LTD Cooper Boot
A brand putting their stamp on a classic can sometimes go very wrong. Luckily, that’s not the case with Marc Fisher LTD’s Cooper Boot. With a slip-on lace and thicker sole, this is a more casual, informal take on the chukka that’s great for Sunday mornings or hopping on your e-bike to the coffee shop.
The Rain Boot
While often not at the top of the list when thinking about boot styles, a pair of rain boots can be a real lifesaver. Depending on which you choose, they can be stylish in the winter and spring, while also (more importantly) protecting your feet from the elements. With a rain boot, you can be a lot more comfortable on that post rain or snow outing knowing your socks won’t get soaked through. And while utility definitely defines the proper rain boot, that doesn’t mean you have to forego style.
Hunter Original Tall Boot
The Hunter Original Tall Boot has that classic shape one wants in their Wellies while also being incredibly sturdy. I’ve had mine for five years while living on a farm and the only thing wrong with them is a bit of discoloration at the heel. While they may not have all the bells and whistles of other boots, they are one you’ll come to cherish and put to work. And, they style perfectly with a Barbour Bedale jacket for that true English gent look.
Le Chameau Chasseur Neoprene Lined Boot
These boots have a bit of an elevated feel (and a higher price point), which may deter some from wanting to really muck around in them. But you should. In fact, I’d argue these boots are better suited for being outdoors in, given the neoprene lining and arch support.
Inspired by the duck boot design, the DIemme Balbi is an elevated shoe for those who don’t want the bulk of a Wellington boot but want to still tramp through the elements unscatched. These are beautifully constructed with a black suede upper and a thick rubber sole. As rugged as they are elegant, it’ll be hard to not hit “Add to Cart” immediately on these bad boys.
The Work Boot
Workwear will always inspire men’s fashion trends. And for good reason. Built to last with a no-frills approach to design and comfort, workwear seems to be something that everyone can agree on. The work boot, with its sturdy design and rugged appearance, can pair with just about anything. Jeans? You’re good. A suit? You’re a rule breaker. In short, style this boot any way you want.
Red Wing Blacksmith
Now this boot is a top-tier boot. It’s the boot you’ll run out of ways to style. Handsomely crafted, versatile, and the perfect shade of brown, the Red Wing Blacksmith has a cult following for a reason. While a bit pricey, it’s a boot you’ll keep for a lifetime – which, really, is the beauty of the work boot.
Eastland High Fidelity Cap Toe
With a refined design that stays a bit rugged, the High Fidelity Cap Toe fits nicely under some selvedge jeans and a chore jacket. The boots go up the ankle somewhat for support, and Eastland adds a Memory Foam insole to keep your foot comfortable for all-day wear.