1. When did boots first walk the earth?
Elizabeth Semmelhack, senior curator of Toronto’s Bata Shoe Museum, said that boots arrived in men’s fashion in the 15th century. Early on, they were “skintight,” like a soled sock that crept up the leg. In the 17th century, the heel appeared, a crucial step on the boot’s journey. The 18th century brought the gentleman’s riding boot.
2. I’m sick of clunky boots. Can you point me to some lighter options that won’t kill my toes?
There is hope yet for your tired puppies. A wave of airily comfortable options—from feather-light, rubber-soled innovations to sneaker/boot hybrids—mean that putting on a boot no longer has to feel like squeezing your foot into vintage ice skates. Above, three ideas for new cushy kicks.
3. Can I wear boots with a suit?
Depends on the boot. Mr. Taffel of Leffot stressed that the most suitable styles are “functional enough to wear in the weather plus dressy enough to wear in the office.” He recommended solid-colored, cap-toe lace-ups like those from English cobblers Edward Green and Crockett & Jones. The shape is “not too bulky, not too chunky” so that “if you had your pant leg over it, it would almost look like you’re wearing a shoe.” Regarding pants, Mr. Arnold at Mr. Porter noted that “proportion is important.” Tight pants with a boot will make your leg look like “a golf club,” while loose, long trousers are sloppy. A straight-cut suit is your best bet with boots, as shown on the gentleman.
4. Has any guy ever pulled off an Ugg?
Tom Brady (above), the ex-spokesman for Uggs, has worn these shearling-lined slipper-boots for years. So if you’re Tom Brady, or his doppelgänger, go right ahead.
5. When it comes to versatility, are black or brown boots better?
While both have their merits, basic brown has the edge. Black “can either look really dressy if it’s a black dress shoe or, if it’s a work boot, it can be cop-looking, that military look,” said Steven Taffel, owner of Leffot shoe stores in Manhattan and Chicago, which sells more brown than black boots. At Mr. Porter, brown similarly outsells black, and its style director, Olie Arnold, said the retailer has recently found success with boots in oxblood, a rich reddish-brown. “Some of the guys in the office are wearing [oxblood boots] with a winter white denim which looks great,” said Mr. Arnold. “It’s not the usual but adds some sophistication to your wardrobe.”
6. How cheap is too cheap for boots?
“We’re talking boots so there’s a bit more material, there’s a bit more to the construction, so I think $200-$400 is a fair range to be in,” said David Mesquita of Leather Spa. Through his work, Mr. Mesquita has seen boots of all kinds and cautioned that cheaper boots can cost you more in repairs in the long run. Still, he is equally wary of expensive “designer boots,” which, despite prices upward of a thousand dollars, may not be waterproof or nearly as durable as their midprice, but less luxe, counterparts.
7. For an obsessive boot collector, what is the Holy Grail?
You can find a boot crafted of lizard skin or even kangaroo skin for upward of a few thousand dollars, but if you’re really looking for brag-worthy footwear, go for a pair of Muhammad Ali’s ring-worn boxing boots. In 2015, his boots from the “Thrilla in Manila” bout (pictured) sold at Heritage Auctions in Chicago for a whopping $119,500.
8. Will cowboy boots give me a sexy strut?
They can, though the heeled boots “might take a little bit of getting used to,” said Mr. Porter’s Mr. Arnold. You want to look natural in them like John Wayne (left), not affected like then-presidential candidate Marco Rubio, who was ridiculed for his high-heeled boots during a 2016 campaign stop in New Hampshire. Worn with dark jeans and sport coats, cowboy boots can even work at the office. As Mr. Arnold reminded us, “confidence is everything.”
9. My boots are wrecked from last winter—shredded soles, dinged toes, the works. Can I salvage them?
In the hands of a good cobbler, just about anything is possible: replacing the sole, fixing a broken eyelet or even swapping out a zipper. David Mesquita, co-owner of Leather Spa, a New York shop that refinishes footwear, advises men to keep an eye on the heel and the tip of the sole; these wear down the fastest but can be a cheap repair. If you have let your boots go completely, he recommended spending no more than 50% of the cost of a new pair on a repair.
10. I’ve heard so many different names for different boots. What do they all mean? And which do I actually need?
WHAT THEY ARE: Ankle boots with elasticated sides. They emerged in the 1840s (after Charles Goodyear invented rubber) and were popularized by the Beatles in the ’60s.
WHY YOU’D WANT THEM: Marrying a comfy fit with a sleek, rounded toe-shape, it’s the boot that everyone could use this fall.
HOW TO WEAR THEM: Versatile, minimalist Chelseas work well with tapered trousers and wider khakis.
WHAT THEY ARE: They share a notched-up heel and bronco-tough exterior with cowboy boots, but ropers are a smidgen shorter.
WHY YOU’D WANT THEM: For a hardy yet handsome Southwestern edge. The cliché holds true: If they’re tough enough for cowboys, they’ll be able to take whatever you toss at ‘em.
HOW TO WEAR THEM: With a plaid shirt and some light denim for the weekend. Yard work optional.
WHAT THEY ARE: Thick leather stompers with a tough rubber sole.
WHY YOU’D WANT THEM: Whether you’re shoveling snow or hauling lumber, or just hope to appear as if you do, work boots are for you.
HOW TO WEAR THEM: If you are actually wearing them for work, pair with coveralls. But if your “work” is more of the graphic-design variety, go for a navy sweater and straight-legged jeans for balance.
WHAT THEY ARE: Stout, two-eyelet casual boots, most often made of suede, they’re descended from the boots that British officers wore in Egypt during WWII.
WHY YOU’D WANT THEM: They’re the loafers of fall—a relaxed kick-around shoe that is easy to walk in thanks to the squishy sole.
HOW TO WEAR THEM: Suede fraternizes nicely with textured slacks in corduroy or flannel.
WHAT THEY ARE: Formal, cap-toe, lace-up boots, derived from calf-high riding boots worn by soldiers in both World Wars.
WHY YOU’D WANT THEM: Despite their front line roots, leather construction and orderly design make them the pre-eminent dress boots.
HOW TO WEAR THEM: These are the boots for a suit, as long as they’re polished enough to satisfy an actual military officer.