Baby, it’s cold outside. But that doesn’t mean your feet need to look like plastic-wrapped marshmallows. Instead of clunky winter clodhoppers, consider snagging a pair of boots that will both keep you warm and have you looking your best.
We spoke with Marisa Meloski, owner and personal stylist at Stilista|Boston, to get her thoughts on how to style these six pairs of men’s boots for the long, cold winter ahead.
Tobias Shearling-Lined Leather Boot, Overland Sheepskin Co.
Price: $299
Initial reaction: The shearling lines the entire interior of the boot (other than the top of the toe box), making for a wear that’s both super warm and super comfortable. The profile manages to be sleek despite a fairly aggressive lug sole, the nubuck leather is both hardy and stylish, and the graphite color will stand out amid the usual crowd of black and brown winter boots—without calling too much attention to itself.
Marisa’s advice: Style with the expected workwear essentials like denim or duck canvas, or elevate with corduroy or a flannel trouser. Top with a classic crewneck sweater in the former example, but opt for a turtleneck, shawl collar pullover or cardigan with more style for the latter. Remember that you bought gray boots for a reason: you must own a lot of it! Coordinate your sweater to your boots or create a tonal base by pairing the boots with gray bottoms, no matter the fabric.
Final thoughts: A solid, versatile choice for everyday wear. Also, the brand recently opened a store in Portsmouth, New Hampshire, giving you a chance to try them on before you buy them.
overland.com/products/mens-tobias-shearling-lined-leather-boots-55825
Brixen, Koio
Price: $395
Initial reaction: Made in Italy, lined with shearling, and outfitted with Koio’s ArcticLug outsole, the Brixen has a hiking-inspired design. Koio advertises the boot as feeling at home in a “snowed-in city, as well as a destination ski resort,” and that feels right. But pair with a thick sweater, a dark overcoat, and a good pair of jeans, and this pair should take you practically anywhere you need to go.
Marisa’s advice: The speed hooks and round laces give an authentic hiking boot aesthetic. Pair with a straight leg pant with a “regular” or “classic” fit that will have the width to fall over the boot shaft. A thick sweater, preferably of the Fair Isle variety, is a timeless choice to top off the look. Extra credit if you have a shearling jacket in a flight or biker style to throw over your shoulders when you head out the door.
Final thoughts: This is why Marisa’s the stylist and I’m not. I’m embarrassed to admit that even though I traveled to Scotland a few years back, I didn’t even know what a Fair Isle sweater was until just now. I may look into getting one.
https://www.koio.co/products/brixen-in-nero-mens
Ranger II Hiking Boot, Lucchese Bootmaker
Price: $425
Initial reaction: These have a traction outsole, and Lucchese says they’re up for “climbing a mountain or building a cabin.” Personally, I’m not sure I’ll want to risk scuffing the gorgeous leather, but I do think these will allow me to dress up a bit in the winter without having to worry about falling on my butt.
Marisa’s advice: These boots have an impressive fashion range. Suit up in denim, a reverse weave sweatshirt, ball cap and a camel overcoat for your weekend coffee run, or pair with chinos, a classic blue oxford-cloth shirt, thick belt in matching chocolate and a wool herringbone blazer for your business casual office.
Final thoughts: Okay, I’ll try hiking in them at least once. (But I’m not building any cabins!) After that, though, I’ll be tempted to use Marisa’s advice as an excuse to buy a nice camel-colored coat. Note: Unlike the other boots on this list, the Ranger II is not insulated. However, the boot does come in wide sizes, leaving plenty of room for a thick wool sock.
lucchese.com/collections/mens-after-ride-boots/products/ranger-ii-hiking-boot-chocolate
Northbound 6” Waterproof Insulated Lace Up, Chippewa
Price: $180
Initial reaction: Chippewa makes work boots, but the wheat nubuck leather of this pair gives street-style vibes—to me, at least. This is the only fully waterproof boot on this list, and I see it transitioning seamlessly from a slushy sidewalk to a casual night out with friends. For someone looking for a darker brown, other Chippewa options include the Classic 2.0 6” Lace Up in the wood colorway, or the Graeme 6” Waterproof Comp Toe Hiker in brown.
Marisa’s advice: Due to the proportions of these, it will be very hard to style them in a “fashion” outfit. Pair them with a mid-tone blue selvedge denim, a long-sleeve thermal Henley, heavy canvas, flannel-lined chore coat, and a wool beanie. Lean into the workwear aesthetic rather than trying to escape it.
Final thoughts: I’m going rogue on this one. Marisa knows her stuff, but despite the workwear form factor, these don’t feel all that big on feet. They’re definitely more casual than some of the other boots on this list, but I’ll get plenty of wear out of them in just jeans and a nice sweater on wet winter days.
Find them: Chippewa boots can be found at Pennyworth’s in Lynn and Newburyport, Off Broadway in Danvers, and Work n Gear in Saugus.
chippewaboots.com/en/northbound-6-inch-waterproof-insulated-lace-up-21096.html
Shearling Boot, Toscana USA
Price: $678
Initial reaction: The detailing on this boot—from the buffalo calf upper, to the ostrich padded color, to the crocodile skin accents—scream “luxury” to me. (Add in the shearling lining, and you have a veritable menagerie on your feet!) Toscana, a small company run by a father-and-daughter team, uses a patented dip-dye process that results in soft, pliable leather that is comfortable from the first wear, and each pair is 100% made in Italy. Even with the Vibram lug sole, the boot is much lighter in weight than it looks.
Marisa’s advice: These are so gorgeous! I envision dark denim, a dress belt, a fitted merino wool or cashmere polo sweater, and a sport coat in a rich, textured, or patterned seasonal fabrication. Everything is slim-fit, sleek and impeccably tailored. Navy dress coat and richly colored scarf to coordinate with the sport coat complete the ensemble.
Final thoughts: In The Departed, a real estate agent is showing Matt Damon’s character a swanky apartment on Beacon Hill and tells him, “You move in, you’re upper-class by about Tuesday.” That’s a little like what it feels like putting these boots on.
toscanausa.com/products/shearling-boot
Shasta Boot Tall, UGG
Price: $500
Initial reaction: Whoa! That’s a lot of boot. UGG advertises this pair as being “maximalist” in both performance and style, and it’s impossible to argue with that assessment. Reaching halfway to my knee and lined generously with UGGplush insulation, this boot is rated to withstand temperatures as low as -26 degrees Fahrenheit. For someone with a street-style aesthetic, this boot is going to put their outfit right over the top.
Marisa’s advice: While I appreciate the full-throttle design, this boot is not for the masses, nor for everyday wear. Unless you are enjoying après ski in Aspen, you risk looking like an extra in a ’90s hip-hop video.
Final thoughts: I’m determined to find a way to pull this one off (although I would have an easier time of it if I were 15 years younger and maybe 75 percent cooler). While I think Marisa is right that this isn’t for the masses, I also think that’s the sort of the point of this boot. If you opt for the Shasta Boot Tall, two things are certain: Your feet will be warm, and you will get noticed.
Find them: UGG footwear can be found in many retail stores including Mark Adrian Shoes in Gloucester, Pennyworth’s in Lynn and Newburyport, and Sun & Ski Sports in Woburn.