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. 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: Shoe The Bear Curtis Cap Toe – $195
- Skimp: Beckett Simonon Nolan Brogues (Blake) – $229
- Spend: Grant Stone Cap Toe Boots (GYW) – $345
- Spend: Löf & Tung Kingsley (GYW) – $376
- Splurge: Allen Edmonds Dalton Wingtip Boots (GYW) – $295 ($445)
- Splurge: Alden “Phoenix” Straight Tip Boots (GYW) – $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 (Aldens, shown above) with a crisp button-down dress shirt, a knit or grenadine tie, and a pair of sleek wool dress slacks in a slim, tapered cut.
Chelsea Boots (or Jodhpurs)
- Skimp: Bostonian Somerville Hi – $95
- Skimp: Meermin – $240
- Spend: Grant Stone Chelsea – $312
- Spend: Allen Edmonds Liverpool – $345 ($495)
- Splurge: Löf & Tung Albanel – $380
- Splurge: RM Williams Craftsman Wholecut – $495
Chelsea boots are those 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 the style is so versatile and comes in so many different iterations. My personal favorites are those with smooth black leather (RM Williams, shown above) or warm brown suede.
Chukka Boots (dressy)
- Skimp: Meermin – $210
- Skimp: Loake 1880 Pimlico – $215ish
- Spend: Trask Landers – $149.90 – $265
- Spend: Löf & Tung Cole – $371
- Splurge: Carmina Unlined – $525
- Splurge: Alden x Brick + Mortar “Everyday” Chukka – $595
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, as shown on the Aldens above) 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: Chippewa Aldrich – $190 ($295)
- Skimp: Thursday Diplomat – $199
- Spend: Thorogood Wedge – $205
- Spend: Red Wing Rover – $269
- Splurge: Grant Stone – $340
- Splurge: Nicks Falcon – $529
- Splurge: Alden Indy – $573 (a version of which is shown above)
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. One of the most famous examples of this style? The Alden Indy (shown above). As in… that Indy. For me, these look best with jeans and button-down casual shirts or flannels, but they can certainly work well with a tweedy sport coat and dark denim if done right.
- Skimp: Clarks Bushacre 2 – $60
- Skimp: J.Crew MacAlister – $148
- Spend: Clark’s Originals – $150
- Spend: Astorflex Greenflex – $165 (shown above)
- Splurge: Red Wing Weekenders – $230
- Splurge: Drake’s Clifford – $365
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.
- Skimp: Merrell Moab 2 – $135
- Spend: Danner Vertigo 917 – $220 (shown above)
- Splurge: Unmarked.mx Yulka 02GXL – $350
I think we all could use a bit more time outdoors, especially this year, so with that in mind, you should have 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: SWIMS Classic Galosh Overshoes – $50+
- Spend: XTRATUF 6” Deck Boot – $95
- Splurge: LL Bean Boots 8” w/ Thinsulate – $159 (shown above)
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: Tecovas Earl Ropers (GYW) – $245
- Spend: Löf & Tung Champlain (GYW) – $404
- Splurge: Lucchese Jonah Ropers (GYW) – $795 (shown above)
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 work boots or the sleek Chelsea boots.
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!