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 my favorite season 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, we’re already seeing daily temperatures around 70°F and nights encroaching on 50°F, so you know what that means! Bust out the jackets, sweaters, hoodies, heavy denim, thick 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 by rough price tiers:
- Skimp: Up to 200ish – Usually glued construction, rarely GYW, some materials are subpar.
- Spend: Up to 400ish – Usually Goodyear welted, better materials, and better quality control.
- Splurge: Over 400 USD – Almost always stitched construction with better materials and great QC.
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 quality.
- Skimp: John Doe Cap Toe Boots in Oiltan Cognac – $217
- Spend: Thursday Boots Wingtip in Black Calf – $235
- Spend: Spier & Mackay Jumper Boots in Dark Brown Calf – $278 (shown above, review here)
- Spend: Grant Stone Cap Toe Boot in British Tan Calf – $350
- Splurge: Allen Edmonds Dalton Wingtip Boots in Walnut Calf – $375 ($475)
- Splurge: Alden 3912 Straight Tip Boots in Dark Brown Calfskin – $595
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.
Chelsea Boots (or Jodhpurs)
- Skimp: BP Water Resistant Suede Chelsea Boots in Chestnut – $100
- Skimp: Thursday Boots Cavalier in Dusty Suede – $190
- Spend: Nisolo All-Weather Chelsea Boot in Tobacco – $230
- Spend: Charles Tyrwhitt Goodyear Welted Suede Chelsea Boot – $249 (shown above, review here)
- Spend: J. Crew Kenton Chelsea Boot in English Waxed Suede – $298 ( lug sole = better for casual wear.)
- Spend: Grant Stone Chelsea Boot in Black Calf – $328
- Splurge: Allen Edmonds Liverpool Chelsea Boots in Black Calf – $346.50 ($495)
- Splurge: R.M. Williams x J.Crew Gifford Boots in Brown Leather – $545
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 slimmer-fitting, tapered dress pants or denim because the style is so versatile and comes in so many different iterations. My personal favorites are those with smooth black or brown leather or a warm brown shade of suede.
Chukka Boots (dressy)
- Skimp: Nordstrom Maddox Chukka Boot in Brown – $110
- Skimp: Thursday Boots Scout Chukka in Brown Leather – $149
- Spend: Frye Boots Paul Chukka Boots in Cognac Leather – $298
- Spend: Grant Stone Chukka in Crimson Chromexcel – $328
- Splurge: Allen Edmonds Williamsburg Chukka Boots in Coffee – $445
- Splurge: Alden 1492 Unlined Chukka Boots in Dark Brown Suede – $577
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 rubber sole will help keep things visually trim and tailored instead of a chunky casual one.
Heritage Work Boots
- Skimp: Golden Fox 6” Boondocker Service Boots in Brown – $120 (review here)
- Skimp: Thursday Boots Diplomat in Burnt Copper – $199
- Spend: White’s Boots Perry in Dark Brown Distressed Leather – $270
- Spend: Spend: Grant Stone Brass Boot in Earth Waxed Commander – $298
- Splurge: Allen Edmonds Higgins Mill Suede Boot with Lug Sole – $445
- Splurge: Alden 405 Original Indy Boot in “Light Brown” Leather – $579 (review of the Indy 405 here)
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.
- Skimp: Clarks Bushacre 3 in Beeswax Leather – $75 (review here)
- Skimp: Thursday Boots Scout in Safari “Rugged” Leather – $149
- Skimp: J.Crew MacAlister Chukka Boots in Estate Brown – $168
- Skimp: Astorflex Greenflex in Stone Suede – $195
- Spend: Grant Stone Chukka in Tan Suede – $292
- Splurge: Drake’s Clifford Desert Boot in Tobacco Suede – $395
- Splurge: John Lofgren Desert Boots in Tobacco Suede – $500
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.
- Skimp: Merrell Moab 2 Mid Waterproof Hiking Boots in Earth – $135
- Skimp: J.Crew Nordic Waterproof Hiker Boots in Navy Snuff – $198
- Spend: Danner Vertigo 917 – $220 (shown above)
- Splurge: Danner Mountain Light Hiking Boots – 390
I think we all could use a bit more time outdoors, especially this year, 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 miles down the trails.
Foul Weather Boots
- Skimp: Xtratuf Deck Boot 6” in Chocolate – $95
- Skimp: Sorel Cheyanne Metro Lace Boots – $155
- Skimp: Huckberry All-Weather Duckboot II – $188 (shown above)
- Spend: Blundstone Super 500s in Rustic Brown – $200
- Splurge: LL Bean Boots 8” w/ Thinsulate – $209
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, and 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 the LL Bean Boots with the warm Thinsulate liner.
Bonus! Roper/Cowboy Boots
- Skimp: Rhodes Roper Boots in Mojave Suede – $210
- Spend: Tecovas The Earl Roper Boots in Bourbon Calf – $245
- Splurge: Lucchese Jonah Ropers (GYW) – $795 (I know I know!)
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!
This post originally ran in 2017 but has since been updated with current product suggestions. And yes, some of the product suggestions above are gonna feel beyond the “normal” Dappered budget. But Adam is our expert on these things. He knows his onions. And his own onions? They might cost a few more bucks than your onions or my onions. And that’s just fine, because shoes and boots are his thing. Onions!