
Pros
- OG classic boot that will never go out of style
- Lug sole grips the ground and keeps every step stable
- Pairs well with denim, cargos, and winter fits
Cons
- Heftier than a dress boot
If I had to recommend one pair of lace-up boots that can do a little bit of everything, I’d start with Timberland’s classic, wheat-colored boots. The brand has been making boots since 1973, and this silhouette has grown from practical workwear into a menswear icon. Often nicknamed the “Butters,” they’re instantly recognizable for their golden nubuck leather, high-top profile, and chunky lug sole. From my teens up until now, they’ve earned a spot in my rotation. And boots that have that kind of staying power, or work with as many outfits.
Another part of the reason they’ve been around for so long is because Timberlands move between style categories. They’re rooted in workwear, but their influence runs deep in hip-hop, streetwear, and sports culture, too. Timothée Chalamet has even put them to work on a red carpet. And with the ’90s and early-2000s aesthetic still in style, the boots feel right at home alongside relaxed-baggy pants, boxy jackets, and layered knits. I’ll wear mine with relaxed denim for an easy everyday fit, but they also play well with cargos and heavier winter layers. They’re definitely heftier than a sleek dress boot and take a few wears to break in, but the laces let you adjust the fit to your liking.
| Upper | Leather |
| Outsole | Rubber |

Pros
- Waterproof membrane seals out moisture
- Pig suede leather and breathable mesh upper
- Air cushion in the heel absorbs shock and adds stability
Cons
- Not the most stylish pick
Merrell’s offering is perfect for avid hikers because it’s designed for days when the weather can turn and the terrain gets rocky. The waterproof membrane seals out water while allowing moisture to escape, and the combination of pig suede leather and breathable mesh gives the upper durability and ventilation. I also like the bellows tongue, which helps keep dirt and trail debris from sneaking inside. Underfoot, an air cushion in the heel absorbs shock and adds stability over uneven ground. It’s not the most stylish boot, but you can get away with wearing it to a casual lunch in the park.
| Upper | Pig suede leather |
| Outsole | Vibram TC5+ |
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Pros
- Mix of leather and suede gives unique contrast on upper
- Blue-toned metal eyelets add a stylish touch
- Sturdy lug sole keeps you planted
Cons
- Limited colorways (but this is the best one)
When I want a lace-up boot to be the star of the show, I put on this pair from Steve Madden. At 5.5 inches tall, the shaft hits around the ankle, giving the boot a chunky look without coming too far up the leg. The mix of black leather and suede gives the upper a nice contrast in texture. It also has a sturdy lug sole and chunky 1.5-inch heel that give it a rugged-meets-fashion-forward look, which adds a little edge to even the most basic jeans-and-tee combination.
I love how they go with dark-wash or black denim, where the monochromatic color palette lets the boot’s texture and hardware do the talking. The standout detail is the blue-toned metal eyelets where the laces thread through, which breaks up the all-black build.
| Upper | Leather and suede |
| Outsole | Rubber |

Pros
- Made with heat-activated insole
- Comfortable from first-day wear
- Lightweight and water-resistant
- Available in a few different colors
Cons
- Size down if you're in between sizes
Our grooming editor, Sean Zucker, put Amberjack’s Chukka through its paces and was impressed by how comfortable it felt right out of the box. The full-grain leather upper and soft sheepskin lining give it a refined finish. The best feature is the heat-activated insole, which gradually molds to your feet with wear over time. The brand paired it with a lightweight outsole that feels more like a cushioned sneaker than a traditional boot. Zucker wore it on rainy commutes, into the office, and around the city on weekend errands, without dealing with sore arches or slipping on wet sidewalks during his testing. I’d put this firmly in the smart-casual category: It works especially well with chinos and tailored trousers, but looks just as natural with dark denim.
| Material | Full-Grain Leather |
| Outsole | TPU |
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Pros
- Made with waterproof, breathable membrane to seal out moisture
- Great for carpentry, framing, warehouse, landscaping, roofing, electrician
- Heat resistant outsole
Cons
- I wouldn't recommend for any other setting besides work
If your job keeps you on construction sites or any other settings that require you to be on your feet for hours at a time, Keen’s waterproof boot is built with that kind of workday in mind. Home builder Matt Risinger recommends the style from the brand because “the break-in period is nonexistent”. The carbon toe cap helps protect against impact and compression, and it weighs 15% less than as traditional steel toe. The waterproof membrane seals out while allowing sweat to escape, and the oil- and slip-resistant rubber outsole adds traction on the job. I also like this option’s overall aesthetic, which resembles a high-top sneaker versus bulky work boot. Underfoot, brand’s proprietary lightweight midsole delivers energy return, giving responsive cushioning for those long shifts when you don’t have the luxury of sitting down.
| Upper | Textile |
| Outsole | Rubber |

Pros
- Designed with top-grain cowhide leather upper for long-lasting style
- Cushioned insole and arch support
- Plays up the heritage workwear vibe
Cons
- Sturdy at first, but breaks in after a few wears
I’ve always liked the look of a classic moc toe boot, especially when I want something rugged that works with the rest of my wardrobe. Quince’s moc toe boot gives me that heritage workwear vibe without the Red Wing Boot price tag. I’ve worn mine with a sweater and cream-colored trousers for dinner. This contrast between the sturdy boot and lighter pants keeps the outfit from feeling too heavy. The top-grain cowhide leather delivers that traditional, broken-in look over time, and the Goodyear welt construction provides long-term durability, so I won’t have to buy another pair next year.
Underfoot, the non-marking rubber wedge outsole provides traction, and the removable OrthoLite insole adds cushioning and arch support for days when I’m walking around downtown New York City. It has the kind of sturdy feel I want from a moc toe, but the styling is versatile enough for casual office days or semi-dressy occasions.
| Upper | Top-grain cowhide leather |
| Outsole | Rubber |
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Pros
- Made with quality construction
- Cushioned and arch support
- Plays up the heritage workwear vibes
Cons
- Super sturdy at first, but breaks in over time
I’ve always liked the look of a classic moc toe boot, especially when I want something rugged that works with the rest of my wardrobe. Quince’s moc toe boot gives me that heritage workwear vibe without the Red Wing Boot price tag. I’ve worn mine with a sweater and cream-colored trousers for dinner. This contrast between the sturdy boot and lighter pants keeps the outfit from feeling too heavy. The top-grain cowhide leather delivers that traditional, broken-in look over time, and the Goodyear welt construction provides long-term durability, so I won’t have to buy another pair next year.
Underfoot, the non-marking rubber wedge outsole provides traction, and the removable OrthoLite insole adds cushioning and arch support for days when I’m walking around downtown New York City. It has the kind of sturdy feel I want from a moc toe, but the styling is versatile enough for casual office days or semi-dressy occasions.
| Upper | Top-grain cowhide leather |
| Outsole | Rubber |
As the Style and Reviews Editor for Men's Health, Joseph covers all-things fashion and grooming. Previously, Cheatham was a commerce editor for Spy, and he has written for Travel + Leisure.
Christian is the Style and Reviews Director at Men's Health and Women’s Health, where he oversees shopping and style content for both brands. He started his magazine career as an accessories assistant at Vogue, and has since held editorial roles at Tatler Asia and The Manual. When he’s not online shopping, you can find him on long walks with his two corgis.
