The 6 Essential Boot Styles And When To Wear Them + 12 Picks

Our picks for the best men's boots that have maximum versatility, with affordable and splurge options.
The 6 Essential Boot Style + 12 Picks

The President in Grizzly Wheat from Thursday Boots. Special thanks to Thursday Boots for teaming up with us to make this post possible!

In a world of near-infinite choices when it comes to footwear, a modest proposal: the boot should be your go-to. Your workhorse. Your daily driver. Your standby.

Why?

Boots are one of those rare items that thrive in nearly every role you throw at them. They look great, are highly functional, and bestow the kind of confidence you get from that marriage of form and function.

Style-wise, they’re highly versatile. Dress ‘em up or down; pair brown boots with black pants and vice versa; wear ‘em with jeans or a suit – they compliment to your look by adding a rugged edge.

Functionally, they keep your feet protected, dry, and stable in a range of conditions, and that functionality feeds the enjoyment you get from wearing something that’s timeless and polished.

They’re an investment in your look, and while they might set you back more than a pair of sneaks, choose carefully and practice proper boot care and you have an item you’ll use for years.

When you’re looking for your first pair of quality boots or just rounding out your closet it’s worth taking a moment to consider how, and where, you’ll be using them.

After all, you want to make sure you’ll be able to wear them as often as you want for your favorite looks and social settings.

Nearly 10 years of observing style trends and building outfits for every conceivable occasion has led the staff here at Primer to distill men’s boots into these six categories, with notes about style and picks at two price points – affordable and splurge.

Must-Have Features in a Quality Boot

There are certain best practices in bootmaking that separate the consumer stuff from a pair of lifer boots.

First: quality leather. The Horween brand is the standard-bearer. Since 1905 they’ve produced a variety of leathers, each highly regarded for the attention to quality and consistency. Horween is a name premium brands use to demonstrate the quality of their materials. It’s not the only game in town, but you won’t go wrong with it. These days, most leather is chrome tanned, yielding a soft, stain resistant leather. Vegetable tanning is considered more artisanal (and consequently more rare). Both methods will give you a quality, rugged boot.

Then there’s Goodyear welt construction, a method for attaching the sole of the boot to the leather upper that ensures they’re waterproof and resoleable. Don’t buy without it. The alternative to a hand-stitched welt is using glue to attach the sole to the upper. While this lowers the cost, it also means your boots will likely fall apart in a season or two.

You should also look out for functional comfort features, including full glove leather interior lining, which lends a soft feel right out of the box. Comfort strips and cork-bed midsoles line between the foot bed and the sole, and help with shock absorption. It’s worth considering: if a pair of boots don’t feel nice on your feet you won’t want to wear them into the ground, and that’s the goal.

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And of course, what style fits your needs? Here’s six of the best classic mens boot styles.

1. The Low Profile Service Style Boot

This type of boot is the lower-cut version of the calf-length combat boots of WWI also known as a Trench Boot or Pershing Boot, and have been made hugely popular since the Wolverine 1000 Mile re-release in 2009. It’s great for the guy who leans smart casual in his wardrobe choices. The low profile, toe box, and thin sole give the boots a more dressy appearance, but with a rugged, vintage, minimalist feel.

Our affordable pick: Thursday President in Grizzly Wheat

Our expensive pick: Wolverine Original 1000 Mile Boot

The service style boot is perhaps what most think of when they think “boot,” and it’s ideal for the guy who wants his boots to be his dressier casual/smart casual go-to.

One thing to be aware of: The Wolverine 1000 Boot boasts a flat leather sole, like a dress shoe, while Thursday boots are fitted with a studded rubber sole that lends more traction – something to consider if you’ll be wearing your boots in inclimate weather.

2. The Wingtip

Wingtips carry a connotation of formality nowadays, which is funny considering that wingtips with broguing (the holes and perforations) have historically been considered casual and sporting attire.

They were traditionally worn for hunting and those who know their Sherlock Holmes remember brogues were a mark of working class characters.

But that was then, and this is now – from Wall Street to Portland, snappy office warriors rock wingtips for an extra bit of polish to their look.

Our affordable pick: Thursday Brown Wingtip

Our expensive pick: Allen Edmonds Dalton Wingtip Dress Boot

Wingtips without an overly chunky sole pair great with a suit or with smart office casual, depending on the formality of your workplace. Some like the two linked here are essentially beefed up dress shoes with an ankle covering, making them more than acceptable to be dressed up in the winter months.

3. The Moc Toe

Perhaps the most distinctive look in our roundup, the moc toe with a white wedge sole have a long association with men who work with their hands on construction sites and in workshops. This lends them a heritage feel that calls back to the steel mills of the 1970s.

Our affordable pick: Thursday Diplomat in Cognac Suede

Our expensive pick: Red Wing ‘875' Moc Toe

Named for the moccasin-style toe, these boots are best for rugged, casual applications.

Of note with the Thursday Diplomats is the suede-specific waterproof compound WeatherSafe, which means you never have to worry about a Seinfeld situation when it comes to the elements.

4. The Chukka

Chukkas: the surprising chameleon. They can be worn casually like a suede chelsea-style boot, or dressed up with trousers and even some suits.

The origin of the term Chukka is a bit of a mystery, with some contending it comes from polo (where “chukka” is a period of play).

tweed sport coat with chambray shirt gray jeans and suede chukka boots

Primer founder Andrew wearing the Scout chukka boot – check out the full look

Andrew dressing down his Thursday Boot chukkas with a t-shirt and gray jeans

The origin of the boot isn’t in dispute: British soldiers wore a version of Chukkas in the Western Desert Campaign of WWII.

That rugged, sandy legacy is evoked in these simple, elegant boots.

Our affordable pick: Thursday Scout Chukka

Our expensive pick: Loake 1880 Kempton Chukka Boots

5. The Chelsea

Highly popular in urban streetwear, the Chelsea has been a mainstay of minimalist fashion-forward attire for a generation now.

Paired with black jeans, a t-shirt, and denim jacket, the laceless design complements more minimalist and monochrome outfits.

Our affordable pick: Thursday Duke Chelsea Boot

Our expensive pick: Oro Chelsea Boot

Perhaps the best-known ambassadors of Chelsea boots are the Fab Four, who made them a trend in the early 60s with their early period mod look.

best boots for men

Throwback mountain boot: Blarney Commander

6. The Throwback Mountain Boot

Casual, chunky, and rugged, this style has evolved with time from the vintage alpine mountain boots of the teens and twenties. While we wouldn’t recommend trying any technical ascents in them today, they lend a hint of the outdoors and something classic to your look.

Our affordable pick: Thursday Commander

Our expensive pick: Danner Mountain Light

Which boot style is your go-to? Chat with me in the comments!

Stillman Brown is a writer and TV producer who has created prime time content for National Geographic, Discovery, Travel Channel and many others. His interests span science & the natural world, personal growth, and food. He lives in Tulsa, Oklahoma.

  • Zac Silk

    Mostly it’s chelseas for me, being from the U.K they’re pretty ubiquitous around here but for good reason.

    I normally dress them down with an Oxford and some dark denim, but I’d like a service boot next as they seem really versatile. https://uploads.disquscdn.com/images/afcbc5133117e7dddbf96aabe5b33fb1ae6b307616145f74ab89f0bb6a0c23fc.jpg

    • http://www.primermagazine.com/ Andrew

      Looks great! Dig the colors.

      • Zac Silk

        Thanks Andrew, I’m thinking of a black pair of Chelsea’s next will defiantly be looking into Thursday’s as they ship internationally.

  • Zach

    Have the boots gotten any better in the last two years? Originally this company was a Kickstarter that over-promised and failed to deliver, with poor leather quality, synthetic tongue, plastic welt, and inconsistent build quality.

    If they’re built like sneakers, they’ll age like sneakers and grow uncomfortable over time rather than break in like you’d expect from a boot. 200 bucks is a lot for a pair of hit or miss boots that can -at most- be said to last two years so far.

    That said, I’ll pick up a pair myself and see if your sponsored posts can be trusted. Thank you at the very least for reviewing an affordable boot. It’s tough to find one in the 200 dollar price range that isn’t a complete mess, or a rare sale from a more established company.

    • Shawn

      If it helps, I bought the Thursday Captain boot early this year, and it has been incredible. Break in took almost no time and they are still incredibly comfortable. The quality is top notch, and they easily survived a wet Colorado winter dredging through feet of snow with no issues and still look brand new. I would highly recommend them to anyone, and can’t be beat for the price.

      • DanPatrickFlores

        Mind if I ask if you treated the leather at all, or were they weather-resistant out of the box?

    • Josh Littauer

      Zach, I am bought a pair of the Captain boots in February of this year. Wear them every day, and they have only gotten more comfortable. There is a bit of wear in the heal as I shuffle my feet a little more than I should. Regardless, definitely worth the $200.

    • http://www.primermagazine.com/ Andrew

      Hey Zach I have multiple pairs and wear their Roughout Captain more than any other pair I own, including Red Wing, Wolverine etc. It’s my go-to for dates, if that says anything. I do hope you feel like you can trust everything we do at Primer, including our sponsored posts. We would never say good things about a company just because they paid us. I started Primer in 2008, and we didn’t last this long because we accept money to say nice things about products. If we don’t think there’s a portion of our readership that would find a product valuable and useful then we don’t feature it. Turning down partnerships is something I do regularly without hesitation. Anyway rambling aside, hope you dig the boots. Which ones are you going with?

    • Chris Houston

      I had a bad experience with them. Around this time last year I bought a pair of the brown captoe boots and got one with slices and dings in it. The leather also seemed very dry and brittle and they cracked instead of creased when I tried them on. I had communicated with their CS about sizing prior to ordering and found them very responsive and friendly. I emailed with some photos to see if this was normal and their CS completely stopped responding to me. It was extremely unprofessional and disappointing and turned me off as a customer. I think their chukkas and suede boots look nice but their customer service was so bad that I don’t think I’d buy from them again.

      • Nolan Paul Walsh

        Hi Chris- one of the founders of Thursday here. Could you email us at founders@thursdayboots.com – I really apologize for this negative experience and want to make it up to you.

        • Chris Houston

          Here’s what I posted there that Nolan responded to. This was about a year ago. In short, I got a pair of boots with a ton of flaws and customer service stopped responding to me when I asked about whether that was normal. It was very unprofessional and damaged the reputation of the company for me. Thankfully the order was via amazon so I was able to return them despite customer service not answering me:
          I had a bad experience with them. Around this time last year I bought a pair of the brown captoe boots and got one with slices and dings in it. The leather also seemed very dry and brittle and they cracked instead of creased when I tried them on. I had communicated with their CS about sizing prior to ordering and found them very responsive and friendly. I emailed with some photos to see if this was normal and their CS completely stopped responding to me. It was extremely unprofessional and disappointing and turned me off as a customer. I think their chukkas and suede boots look nice but their customer service was so bad that I don’t think I’d buy from them again.

          I’m not sure what he meant when he said he wanted to make it up to me since it was last year.
          Chris

    • Nolan Paul Walsh

      One of the founders of Thursday here…we have come a long way since our ‘bootstrapped’ kickstarter, BUT we have never used a plastic welt on our men’s boots, and we have never used a synthetic tongue or leather. We make our boots literally side by side Red Wings, Wolverines, Lucheese, and other top quality brands. Our leather comes from the top tanneries in North America. We have also hired experienced QC and production specialists to insure top quality products. With handcrafted goodyear welt boots you are always going to have some minor inconsistencies- especially with leathers such as Chromexcel…that’s part of the nature (and charm) of handmade products and the uniqueness of leathers such as Chromexcel. With that being said our defect rate is well under 1/300 and we track it very closely. If you get a boot from us that has a defect or you just don’t like it- we provide free returns. We are in this for the long-haul and we are very passionate about making the best products available to our friends, family and YOU at a great value. We are always reachable at founders@thursdayboots.com and always aim to do right by our customers- no exceptions.

  • rogun

    I just purchased some Blundstones and hope I got the sizing right. They don’t have GYW construction, but the plan is to actually use them for labor. Btw, J.Crew has their Kenton’s on sale atm.

    How’s the sizing for Thursday boots? How does it compare to Chippewa and Red Wing?

  • Navdeep Dadwal

    I love the versatility of boots. I am more into Chukka but after going through the options I might as well try a Chelsea because it looks appealing. I can team them up with almost anything and the final result looks appeasing enough to me. It’s Chelsea this fall though.

  • Stephen Jackson

    As much as I love boots, why do they all have to have 2″ heals? I’m 6’7″ and the last thing I need is to be 2″ taller