One of the best parts about the cooler months? Boots. Sure, you can wear chukkas in the summer (with ease), but other than that, we’re talking about seriously sweaty feet when it’s north of 90 degrees. But that’s not the case this time of year. Now that it’s cooled off, plenty of us are shelving the lighter footwear in favor of sturdy, but still good looking boots. Here’s six of the most common types, and why they might be worth adding a pair to your rotation.
- Allen Edmonds Liverpool – $495 (or $345 for 2nds)
- The Rail Suede Chelsea – $99.95
- Made in the UK Loake Mitchum Chelsea – $196 ($280)
- 1901 Brooks Chelsea Boot – $125
- Banana Republic Tully Sneaker Chelsea – $64 ($128)
- J. Crew Oar Stripe Chelsea Boots in Italian Leather – $298
- EXPRESS Leather Chelsea – $88.80 ($148)
Defined by their laceless, sleek style, Chelsea boots are dressy but not so dressy that they can’t be worn with dark denim. If you’re the type to take some risks, they can also look good with a suit (try skipping the tie). Found in suede or leather, with grip to the soles or not. Getting the right fit can sometimes be an issue, since there’s no laces to cinch up. Find a pair you love though, and you’ll make excuses to wear them.
The Heritage Work Boot
- Huckberry Rhodes Boots – $220
- Original Chippewa 6-Inch Service Utility Boot – $250
- Allen Edmonds Higgins Mill Boot – $395
- J. Crew Goodyear Welted Kenton Pacer Boots – $248
- EXPRESS Leather Chukka Work Boot – $82.80 ($138)
- Red Wing Blacksmith Boot – $300
Hefty leathers, good support, solid construction, and the designs are based in the styles of work boots from a bygone era. Look for boots with uppers that’ll show character over time, and bonus points for a sole with traction, but subtle traction. Super toothy lug boots just don’t walk the line between utility and style like other options do.
- Jack Erwin Mason Suede Chukkas – $195
- Banana Republic Norman Chukka – $89 ($178)
- Florsheim Blaze Chukka – $130
- Allen Edmonds Nomad Chukka – $207 ($345)
- Allen Edmonds x Massdrop Chukka – $239.99 FINAL currently unavailable
- Meermin Chukka – $200 + $35 Shipping
- Nordstrom 1901 Chukkas – $125
An ankle high boot with either two or three pairs of lace eyelets. Much like the chelsea, these are found in suede and leather and can have smooth leather soles, or, a bit of traction down below. Super versatile. Easy to dress up or down.
- Made in Italy Astorflex Desert Boots – $150
- Clarks Bushacre 2 – $72.03
- Clarks Original Desert Boot – $93.82
- J. Crew Made in Italy Macallister Boots in Suede – $148
Sure, there’s some overlap here, but y’know how all squares are rectangles, yet not all rectangles are squares? Right. All desert boots are chukkas, yet not all chukkas are desert boots. Desert boots are noticeably more casual, often with a thicker profile and always with a crepe (or crepe-like) sole.
- Allen Edmonds Dalton – $495 (or $345 for 2nds)
- Meermin Dress Boots – $245 + $35 Shipping
- Banana Republic Jodhpur Boots – $94 ($188)
- Allen Edmonds Sullivan Street Cap Toe Boots – $495
- Jack Erwin Carter Wingtip Boot – $220
- Suitsupply Dark Brown Cap Toe Boots – $329
A category that can cover a wide range of styles. Some might argue that chelseas belong in here, and even some chukkas can go in here too. Whatever the case, they’re sleek and anything but bulbous, share many details with regular dress shoes, and can look great with a suit made from flannel or tweed.
All Weather Boots or Galoshes/Overshoes
- Huckberry Duck Boots – $180
- Sorel Caribou – $180
- Swims Classic OverShoe – $49.97 ($95)
- Made in the USA L.L. Bean Boots – $155
- Hunter Original Chelsea – $89.97 ($150)
For those that live in seriously wet climates, warm or cold. Sometimes, Mother Nature wins out and you gotta go with what’ll keep you dry. Whether it’s clearing the walk of snow, or making your way to work in a downpour, save your good kicks for times when you’re not seriously considering building an ark (or an Igloo).
BONUS Retro Hikers
- J.Crew X Timberland GT Scramble Hiking Boots – $175
- Danner Mountain 600 in Saddle Tan – $200
- Danner Mountain Light Overton – $330
- Vasque Sundowner in Suede – $150 – $220
- Danner Vertigo 917 -$220
Just because a boot is waterproof, breathable, and supportive on the trail, doesn’t mean it has to look like it was designed for hopping about the sea of tranquility. If you’re not the outdoors type, yet live in a semi-mild climate, these can double as winter boots for when the snow starts to (sorta) fly.
This post originally ran in 2017, but has since been updated with current product suggestions.