About the Author: Adam Terry is a thirtysomething salesman in the heating and manufacturing industry. He enjoys bourbon, boots, sneakers, raw denim, and working on on his dad bod father figure.
It’s the most… wonderful time… of the year! No, not that one. Fall is back and it’s a favorite season for many of us because the weather’s perfect – cool, crisp days with sunshine and scattered clouds. Nights get cold enough for blankets and bonfires, but not so cold that you need snowshoes. Here in the Southeast where I (the Adam guy) am located, we’re seeing a change in seasons. So you know what that means! Bust out the insulating and windproof jackets, warm cable-knit or shawl-collar sweaters, heavier-weight denim or thick wale cords, merino wool boot socks, and BOOTS. BOOTS. BOOTS!
From formal to casual, there’s a pair of boots for every occasion. They come in all shapes and sizes and in various price points from under $100 to well over $500 USD, so how do you choose?! Well, I’ve put together this handy dandy guide to help you decide. I’ve also categorized them into three tiers:
- Skimp: Usually under $200 – Choose these when you’re on a budget or trying out a new style. Usually glued construction, rarely Goodyear Welted.
- Spend: Usually under $400 – Choose these when you’re ready to upgrade to something better. Usually Goodyear welted, better materials, and better quality control.
- Splurge: Usually over $400 – Choose these when you have your size and aesthetic locked down.
If you’re in the market for a new pair of boots, it’s really important to set a budget that works for you and your lifestyle. Everyone’s wants and needs are different, so find a number that you’re comfortable with. This will help you narrow down your choices and set some expectations for overall initial quality.
Dress Boots
- Skimp: Thursday Boots Wingtip – $235
- Spend: Grant Stone Cap Toe Boot in Crimson Chromexcel – $380
- Splurge: Allen Edmonds Dalton Wingtip Boots – $285 ($475) (shown above in walnut, although in our photo the lighting makes them look a little more like the dark chili option, which honestly is probably more versatile than walnut.)
- Bonus: Alden Navy HighStraight Tip Dress Boots – $610
We’re all probably aware of the dramatic drop in formal business clothing usage post-COVID. That doesn’t mean there’s not a place in everyone’s closet for a gorgeous dress boot for those occasions where you DO get dressed up – holiday dinners with your parents, a night out at the symphony, or an upcoming wedding. You’re looking for boots that are sleek and smartly polished, so they pair well with suiting or the dressy side of business casual. I like wearing my dress boots with a crisp button-down dress shirt, a knit or grenadine tie, and a pair of sleek wool dress slacks in a slim, slightly tapered cut.
Chukka Boots (dressy)
- Skimp: Thursday Boots Scout – $149
- Spend: Loake Pimlico Chukkas – $330 (shown above)
- Spend: Grant Stone Chukkas – $348
- Splurge: Alden “Everyday” Chukka Boot – $625
The dressy chukka boot lies neatly between formal and semi-casual boots, which means you can dress them up with a suit and tie or dress them down with a sport coat and tailored denim. You’ll want to look for smooth or subtly textured leathers (or suedes) without a lot of embellishments or details. A thinner leather or subtle rubber sole will help keep things visually trim and tailored instead of a chunky casual one (like a thick, toothy lug sole). They also have more visual (and usually more internal) structure than a casual, unstructured, sometimes floppy pair of desert boots. Speaking of…
Desert Boots
- Skimp: Clarks Bushacre 3 in Beeswax Leather – $75 or less (review here)
- Skimp: J. Crew MacAlister Chukka Boots in Suede $158
- Skimp: J. Crew MacAlister Chukka Boots in Estate Brown Leather – $168 (shown above, review here)
- Spend: Huckberry Rhodes Tyler Chukkas – $175 (review here)
- Spend: Todd Snyder Nomad Chukka Boots in Suede – $248 (review here)
Desert boots are the more casual leaning cousin of the chukka boot. Style wise, both traditionally feature ankle height uppers and two or three lace eyelets. The desert boot differs in that they’re typically made from casual leathers or suedes and have soft crepe or rubber soles. I like to pair mine with a simple merino wool sweater, a button-down collared shirt, and a pair of casual chinos or jeans like Steve McQueen.
Chelsea Boots (or Jodhpurs)
- Skimp: Astorflex Bitflex – $215
- Spend: J. Crew Kenton Chelsea Boots in “Color 8” – $298 (shown above = the 2021 version. 2022 could be slightly different leather. Review of 2021 can be found here.)
- Splurge: R.M. Williams Comfort Craftstman – $539 (although at post time with the British Pound doing what it’s doing, you can get them for much less from some UK Retailers, as long as you’re willing to take the risk with paying for any potential international returns. Which’ll be expensive and risky.)
Chelsea boots are sleek, fashionable slip-on boots that the Beatles and Rolling Stones made famous back in the ‘60s. Even today, they’re pretty popular with those of us who like tapered dress pants or denim because this boot style is so versatile and comes in so many different iterations. My personal favorites are those with smooth black or brown leather or a buttery soft brown or tan suede.
Heritage Work Boots
- Skimp: Golden Fox 6” Boondocker Service Boots in Brown – $120 (review here)
- Skimp: Thursday Boots Captain – $199
- Spend: J. Crew Kenton Pacer Boots – $298
- Spend: Red Wing Heritage 1907 6” Moc Toe Boots – $310
- Spend: White’s Lifestyle Line – $310 (shown above, review here)
- Splurge: Allen Edmonds Higgins Mill – $475
- Splurge: Alden 403 Brown Chromexcel Indy – $607
Heritage style work boots are probably the most common boots you’ll see in today’s menswear marketplace. They’re so ubiquitous and common because they’re so dang versatile for most guys. Ever since Red Wing jump started their modern revival back in the late 2000’s, we’ve seen a handful of brands and styles hit the marketplace – the most common being a boot in a tough brown leather with a durable rubber sole and repairable Goodyear Welted construction. For me, these look best with jeans and button-down casual shirts or flannels, but they can certainly work well with a tweed sport coat and chinos if the tailoring and accessories are done right. Imagine the Professor Indiana Jones vibe here.
Roper/Cowboy Boots
- Skimp: Justin Stampede Roper Western Boots – $170
- Spend: Rhodes Roper Boots in Leather or Suede – $248 (shown above)
- Splurge: Majestic Shadow Goat Roper Boots – $440
Here’s something you probably never thought you’d see on Dappered! Roper boots, or sh*t kickers as we call them here in the South, are something of a hybrid between traditional cowboy boots, pull-on work boots, and elegant dress boots. It’s a design that can be traced back to England’s mounted military might of the mid-19th Century where the cavalry troops would wear these short heeled, rounded/pointed toe boots because they were easy to wear while getting into and out of stirrups. Today, they’re an interesting twist and alternative to the classic workwear boots or sleek Chelsea/Jodhpur boots. Don’t be afraid to try something new from time to time! Personally, I prefer basic ropers with minimal “Western” detailing.
Hiking Boots
- Skimp: Timberland Euro Hiker Hiking Boots – $140
- Spend: Danner Vertigo 917 – $230 (shown above, and well worn)
- Spend: J.Crew Cascade Boots in Tumbled Leather – $298
- Splurge: Huckberry x Danner Waxed Canvas Mountain Light – $425
I think we all could use a bit more time outdoors, so with that in mind, you should invest in a decent pair of hiking boots. Ideally, a good pair of boots for a casual day hike will be cut just above the ankle for some support and anti-roll protection. These should flex easily and require little to no break-in time to feel comfortable. Leather and suede are preferable to synthetics, but each has their place. If you’re comfortable spending north of $250, you should investigate Goodyear welted or stitch down options where you can have the upper resoled after a few hundred clicks down your local trails.
Foul Weather Boots
- Skimp: J.Crew x Sperry Cold Bay Rubber Chelsea Boots – $100
- Spend: Huckberry All-Weather Duckboot II – $188 (shown above)
- Splurge: LL Bean Boots 8” w/ Thinsulate – $229
Here in the U.S., the Atlantic hurricane season runs from early June to late November. Thanks to greater temperature differences between the sea surfaces and those aloft, lots of tropical storms form and produce showers, thunderstorms, or much, much worse. With an average of 10 large storms each year, you should be prepared with a pair of foul weather boots that can handle the heavy rainfall, puddles of muck, or the inevitable snow and slush of Winter. Those of you in the Northeast Corridor or Pacific Northwest know what that’s like. Personally, I love LL Bean Boots with the warm Thinsulate lining.