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:
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.
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.
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 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 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 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.
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.
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.
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.
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