Dark, slim denim. A trim fitting oxford shirt. A nice pair of boots. There are only a few things we feel absolutely confident in calling an “essential” for a man’s adventure into dressing well. More so than a navy suit or a v-neck sweater, a great pair of boots has the ability to span casual to dressy outfits in a way no sneaker or dress shoe ever can.
What follows is our list of the best of the best, our favorite boots that have impressed us – some pairs going back to 2010. They feature the best construction methods and leathers, and regardless of your personal style, you’re sure to find a pair that will work hard for you for years to come.
Primer Partner Pick:
Thursday Boot Co. President
Thursday Boot Co. is a relatively new face on the boot scene and my initial reaction was, “do we need another boot brand?” After all, a quality pair of boots are an investment-level decision often running north of half a grand. Treat them right, however, and you have a fixture of your wardrobe for life. With Thursday Boot Co., skepticism was quickly replaced by excitement because they’ve done something pretty revolutionary in this segment: created a sharp, durable product with all the features you want from a lifer boot at half the cost of the established premium brands.
Looking at The President calls to mind Wolverine’s Thousand Mile Boot, the standard bearer for the archival dress boot style. They’re versatile enough to be dressed up or worn casually. And optics are backed up by quality construction: Thursday Boot Co. uses only Tier 1 USA hides to ensure top quality leather. Goodyear welt construction (the best way to attach the sole to the upper, period) ensures they’re both re-solable and virtually waterproof. Unlike a lot of other premium vintage-style dress boots, which use leather soles, Thursday boots utilize studded rubber outsoles – meaning they can actually be worn when there’s water on the ground. Pretty important in a boot, if you ask me.
Thursday boots are handcrafted with a full glove leather interior lining, EVA comfort strips, and cork-bed midsoles for a comfortable fit. Add free shipping and returns and the Thursday Boot Co. President is one of a handful of great options for an affordable, quality alternative to the premium standbys. I’ve owned 3 different pairs now, all holding up just as great as they look.
Now you might be wondering about the name. Why “Thursday?” According to the company’s website, Thursdays are the day of the week you need to be prepared for anything – a work presentation, dinner with friends, a first date. I’d say these boots can pivot any occasion you throw at them.
Red Wing Heritage 6″ Moc Toe
The Red Wing Heritage boot is aptly named: Red Wing has been in business since 1905 and the Heritage is part of an uninterrupted tradition of built-to-last boots stretching back to your great-grandfather’s era. Like many of it’s leather brethren, the Heritage features Goodyear welt construction, but it’s augmented by triple stitching for extra durability.
The moccasin toe and white sole make this a visually striking boot, and there’s a story behind the sole. When originally designed, Red Wing chose a lightweight crepe sole with minimal tread design to reduce the mud that would cling to a farmer’s boots. You might think the classic reddish leather wouldn’t be versatile, but they pair well with any shade of tan, brown and black in the rest of your outfit. Your options are virtually limitless.
One drawback we’re aware of is that Red Wings are notorious for being hard soled, but with a $3 set of insoles from Rite Aid these are my most comfortable pair of Red Wings and have become a casual staple of my wardrobe since I first got them in 2010. Casual and rugged, the Heritage Moc Toe is the perfect cross between style and functionality.
Red Wing Beckman Round
If a boot could offer you a cigar and a glass of speakeasy bourbon, it might be the Red Wing Beckman Round. The Cigar Featherstone dress leather is as durable as any other but implies a depth and class other boots simply don’t. The Beckman Round comes in multiple colors; our favorites are the Black Cherry and Cigar. The richness of the Black Cherry makes for a smart juxtaposition when paired with chinos and sweaters, and go equally well with jeans and a casual sport coat for the marshall Raylan Givens look.
Their chunky style and heel nod to custom fire boots, like Nick’s and White’s, and the price creeps towards custom as well. But you’re getting what you pay for: triple stitching with latex-coated thread for water resistance, Goodyear welts, and a Vibram Roccia sole that’s beefier than other boots in the class.
Red Wing Iron Ranger
The Iron Ranger represents the standard bearer for the Red Wing archival work boot. It’s made in America and features the same Goodyear welt construction and top-quality threadwork of their other offerings. The sole of the Iron Ranger stands out, however. It is nitrile cork, a durable material that sheds water and oil. It won’t dry out and crack like a rubber sole, and is more durable than a leather sole.
Design details like a cap toe (originally added to provide more protection for miners) and a wide back strap give an almost western feel to the boot that pairs exceptionally well with dark selvedge denim. They’re close to the top range for off-the-rack boots, but the Iron Ranger is something you’ll pass on to your son when your boot-wearing days are done.
Thorogood Moc Toe
In the world of boots the Thorogood Moc Toe and the Red Wing Moc Toe are in a perpetual staredown. Both made in the USA with wedge-style soles and Goodyear welts, both handsome devils, both hailing from frigid north midwest states.
So what makes them distinct? The first thing that jumps out at you is the price tag: they’re widely available for around $150, one of the lowest price points in our guide. It isn’t pocket change, but it’s a deal considering the build quality and heritage. Thorogood’s Moc Toe was first introduced in 1964 as the “Hike ’n Camp,” the official Boy Scout Boot and has been selling strong ever since.
Other features that set it apart are a removable dual-density shock absorption footbed and comfort cushion. They’re also available with a hardened safety toe. Perhaps more than any other boot in the category these are meant to be worked in.
While a great boot with silky leather, their notable downfall is that they do run a bit hot on your feet.
Chippewa GQ Apache Lacer
If you’re gun shy about dropping $200 or more for a pair of long-lasting boots we’ve got good news: you don’t have to. Chippewa is another proud American company that’s been crafting and perfecting their product since 1901 and the GQ Apache Lacer is the product of that heritage. Built from 5.5 oz full grain leather, the boots are sewn with a three row stitch pattern on the same machines Chippewa has been using for 100 years. And like other boots in the category, they feature wax-coated thread for all-weather roadworthiness.
Where the Chippewa doesn’t shine is in styling, especially compared to some other, more refined boots in the segment like the dressier Thursday Boots but we appreciate the non-slip Vibram outsole and removable orthotic cushion for their functionality. American handmade for under $150? You simply can’t go wrong with a pair of Chippewas, especially if you’re looking for a more rugged style.
Wolverine 1000 Mile Boot
Founded in 1883, Wolverine has been making the 1000 Mile boot since the early decades of the 20th century – so named because the hardwearing horsehide leather was said to last a 1000 miles of wear.
While we can’t independently verify specific mileage, the modern day revival of the 1000 Mile boot is built to last with a Goodyear Welt and stacked leather sole. Still made in Rockford, Michigan, home of Wolverine’s original shoe and tanning factory, and now constructed of Chicago-made Horween Chromexcel Leather, the 1000 Mile helped launch the vintage service-boot style with the onset of the Americana fashion movement of the last decade.
The leather sole keeps with the original design and creates a sleek profile that allows these boots to be worn with jeans or dress pants. But make no mistake, leather soles are not great options if you’re planning to encounter precipitation. In that case, you’ll want to opt for the recent “Evans” variant that comes with a Vibram lug forepart and heel – which will set you back a cool $400, and alter the silhouette to a more rugged one like the Iron Ranger.
The well known leader of the throwback dress boot category, if you have the $360+ to drop, the 1000 Mile won’t let you down.
Timberland Waterproof West Haven
Originally founded in 1918, The Abington Shoe Company introduced a line of waterproof leather boots in 1973. The intense popularity led to the company being renamed to The Timberland Company. The brand is perhaps most well known for their “yellow boot,” a style you won’t see gracing the pages of Primer very often, but Timberland actually has a wide range of styles that we do dig.
Case in point the West Haven 6” boot – a true looker for a boot that boasts a full grain leather upper and is built with a waterproof membrane. The moc toe is reminiscent of some of the more expensive options on our list, and comfort touches like the anti-fatigue removable footbed makes the West Haven a smart choice if you find yourself trudging through puddles and snow.
The extra liners and waterproofing come at a cost though – like the Thorogood Moc Toe, these tend to run hot on the feet. Not hot enough to be a deal breaker if the boot otherwise ticks off everything on your list, but the heat can be a noticeable.
Grant Stone Ottawa
Grant Stone is the outlier and the enigma of our roundup. New compared to brands like Red Wing and Chippewa, who’ve been around for well over a hundred years, Grant Stone’s founders have been in the boot business in some capacity for just 30 years. Neophytes compared to the old-school giants.
Peer beneath the hood, however, and you have a boot crafted with a unique focus on getting the details right. Beyond the Goodyear welt construction, all Grant Stone boots feature vegetable-tanned leather, which utilizes raw materials from various plants, woods, barks, fruits and leaves for a Chromium free all-natural product.
While at the higher end of the price-point, the Ottawa is one of the more agile and refined boots we’ve seen – the moc toe tapers upward for a sleeker and less chunky profile. The supple, warm leather tones speak of quality and pair well with chinos, cords, or quality jeans. And is a more “budget” alternative to the…
Our most refined entry also happens to be the most bank-breaking, but let me make the case in two words: Indiana Jones.
The Alden “Indy,” technically the model 405, is reputed to be the boot worn by Harrison Ford in the classic trilogy (the more recent effort need not be discussed). In fact, images of Alden 405s we’ve sought out online from real owners make the case better than any marketing copy: they look like the slouchy, world-weary boots Jones wore to uncover treasure, beat back Nazis, and win the girl.
Because of their lower profile, soft toe, and flat sole, the 405s straddle the line between dress and work boot. Compared to Red Wing and Thorogood moc toes they have a more cultured, equestrian look than anything you’d see tromping around at the steel mill.
Alden’s Indy boots are crafted from top-shelf Horween chromexcel leather and break in for a lightweight all-day wear that’s appropriate with jeans, chinos or – if you’re doing it Indiana Jones style – a gray three piece suit for teaching your undergrad archaeology seminar.
We’re excited to partner with Thursday Boots on this post because they’re the perfect Primer boot brand. If their confidence in being listed with 9 of the other best boots on the market doesn’t convince you of their assurance that you’ll love their boots, the specs will: Full grain leather, Goodyear Welt construction, and a price tag that’s half the price of similar boots. The President is one of the only affordable alternatives to the venerable Wolverine 1000 Mile boot and at under $200 it’s a no-brainer.
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