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.
- Rhodes Chukkas – $198 review here
- Allen Edmonds Williamsburg Chukkas – $309 ($445)
- Nordstrom 1901 Barrett Chukkas – $79.97 ($125)
- Banana Republic Norman Chukkas in Leather or Suede – $106.80 ($178) review here
- Made in the UK Loake Plimlico Chukkas via Massdrop – $199 FINAL currently unavailable
- Nordstrom Alton Chukkas – $125
An ankle high boot with either two or three pairs of lace eyelets. 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. Legitimate foundation pieces for a wardrobe.
Heritage Style Work Boot
- Banana Republic Arley Leather or Suede Boots – $106.80 when 40% off ($178)
- Original Chippewa 6-Inch Service Utility Boot – $280 review here
- Allen Edmonds Higgins Mill Boot – $295 – $325 ($395 – $425)
- J. Crew Goodyear Welted Kenton Pacer Boots – $248
- Wolverine 1000 Mile Wedge Boot – $249.97 ($425)
- Huckberry Rhodes Boots – $220
- Red Wing Moc Toe Boots – $280 – $290
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.
- Allen Edmonds Liverpool – $395 ($495) review here
- Nordstrom B.P. Easton Chelsea Boot – $109.95
- New Republic Suede Chelseas – $99
- Nordstrom David Chelsea Boot – $134.95
- Bonobos The Alpern Chelsea Boot – $298
- R.M. Williams Chelseas – $371 ($495)
- J. Crew Kenton Chelseas – $248
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.
- Made in Italy Astorflex Desert Boots – $150
- Clarks Bushacre 2 – $58
- Clarks Original Desert Boot – $100 – $130
- 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 Hamilton Boots – $275 ($395)
- Allen Edmonds Dalton – $309 ($445)
- Suitsupply Dark Brown Cap Toe Boots – $349
- Jack Erwin Carter Wingtip Boot – $220
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 – $134.98 ($180) fingers crossed for a restock
- Made in the USA L.L. Bean Boots – $159
- Sorel Caribou – $180
- Tingley Men’s Storm Stretch Overshoe – $30
- Yak Trax – $18
- XTRATUF 6″ Deck Boot – $95.00
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 Hiking Boots
- Danner Vertigo 917 -$220
- Vasque Sundowner in Suede – $150 – $220
- Danner Mountain 600 in Saddle Tan – $200
- The North Face Back to Berkeley Redux – $130
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. Look for boots with modern materials and performance, yet have a decidedly retro look (see the Vertigo 917 above as a prime example). If you’re not the outdoorsy type, yet you 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.