A Guide to Men’s Boots

January 13th, 2016

Tis the season.

Winter is a chance for your low-cut footwear to rest and recover while you break-out your boot collection.

Following up on our Guide to Loafers, here we break down the essential boot styles for the curated man’s wardrobe.

The Chelsea Boot


Sleek and minimal, the chelsea boot is a slip-on style with a sharp toebox and a slim leather sole. They can work with anything from suits, to chinos, to jeans, but are the best reserved for going out somewhere (or with someone) sexy.

Recommended In: medium brown suede or black leather.

The Captoe Dress Boot


If you’re new to the world of dress boots, aka getting suited and booted, this is a great place to start. A medium height captoe dress boot is smooth enough for your sharpest tailored trousers, and rugged enough for your most beat-up selvedge denim.

Recommended In: dark oxblood leather

The Wingtip Boot


The wingtip brogue is another essential that can serve as your stand-alone dress boot. We’ve featured the “Dalton style from Allen Edmonds as much as any other footwear in AOS history, simply because of their versatility and how long our pairs have lasted.

Recommended In: chestnut brown leather or dark cordovan.

The Suede Brogue Boot


Similar to the captoe dress boot, just slightly more casual in nature due to it’s shorter height, heavy stitching, and napped suede texture.

Recommended In: medium brown suede

The Jodhpur Ankle Boot


This has been a personal favorite of mine lately. Similar to the chelsea boot, but with a 360 ankle strap rather than the elastic side bellies. This is a sleek European style that’s perfect for trousers with tapered trim or slim waxed jeans.

Recommended In: medium brown suede or black leather.

The Chukka Boot


The chukka is a casual ankle boot with short laces and only 2-3 eyelets. It’s a casual style best reserved for jeans and chinos, but a pair in a rich suede can also be a good match for flannel trousers.

Recommended In: tan or light brown suede.

The Harness Boot


The harness boot, or riding boot, is an extremely tough style meant to withstand a real beating and protect your feet from just about anything. These are meant for motorcycle riding, or doing some hardcore shit-kicking.

Recommended in: the toughest leather you can find.

The Desert Boot


A form of Chukka boot designed by the military, with flexible gum soles, for dry dusty terrain. The most popular version of these is by Clarks, due to their affordability, comfort and longevity.

Recommended In: waxed leather.

The Work Boot


Whether they’re classic Timberlands or Red Wings, the work boot, as with workwear, will always have a place in menswear. These are steel-toed and cut from a thick cowhide to protect your feet and give you plenty of stomping power.

Recommended In: heavy-duty medium brown leather.

The Rocker Boot


This one is for the rockstars and skinny-jean wearing party animals out there. These are best suited for thin-framed musicians and artists who aren’t afraid of a little androgyny.

Recommended in: black, of course. Exotic skin (like python) if you’re really trying to go all-in.

The Cowboy Boot


The cowboy boot is a western style with a long history. They’re not for everybody, but for a Southern Rancher like Alex, they can go from horseback to formal occasion in just a matter of a shine.

Recommended in: a natural, understated, non-embellished leather. Preferably vintage.

The Alpine Boot


This one if for snowy days, ski trips, and fashionable hiking excursions. A sleek enough pair, like the ones above, can also be great for trudging to the office through some nasty conditions.

Recommended in: dark brown or oxblood (although these do look badass in a black)


Thanks, as always, for reading. If you have any questions about our online custom menswear, feel free to contact us anytime. We look forward to serving as your personal tailor and stylist. 

Yours in style,

Dan Trepanier

Shop Custom Menswear Made in America


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  • Ralph

    I’d like to find a boot like the forth from the left in the first picture. Do you know where to buy that?

  • Cowboy Hank

    What’s the boot in the second picture?

  • Dean Wiersma

    Personally, I use plain black rubber boots to and from work. I tuck the suit pants into the boots and ditch them as soon as I can. This seems to work for the equestrian crowd. A good pair of paddock boots is another option.

  • Megan Pritchard

    Which boots are featured in the Alpine picture?

  • JoeFromTexas

    hmmm – I left a comment (a brilliant one at that… I think, I don’t really remember), but it disappeared. Perhaps there’s a glitch in the matrix somewhere?

  • Simon

    Question for Canadian Dan.

    I live in Montreal. You know what that means : a lot of snow, “slush”, ice, large puddle on every corner, freezing temperature… I want to look dapper head-to-toes to go to work (lawyer-to-be) so I need boots to go with my suits, but I need something rugged, waterproof, warm that still look like a million dollars. Any suggestion ?

    • Arianna

      Also in Canada, not Montreal but the other side of the country. I kept shoes at work (heels actually, since I’m a girl) and just wore boots to work. My boyfriend just wears regular dress shoes to work even in the summer though, and gives them a quick scrub down if they get yucky when he gets to work (just with a shoe mitt or whatever he keeps in his drawer). He also works in a law office.

      • Simon

        Your solution is what I’m going for. I will leave my dress shoes in my office. My question was more about which boots to buy. I have those big leather construction worker boots that fit with pretty much anything but a suit. I need something warm and waterproof that can fit with a suit.

        • tommyjohn_45

          Dan’s sporting the Alpine boots above with a suite (at least suit pants) I believe. If you want to steer away from the rugged look, you could always wear galoshes over your leather shoes.

          I personally go with LL Bean duck boots, as they have a special place in Boston and probably more widely accepted with suits than they would be elsewhere.

          • Simon

            Those LL Bean duck boots are all I need (rugged, warm, waterproof) but not what I want (dress boots). I might give a try to galoshes. Or I’ll just give up and resign to look out of style on my commute from home to work with big ugly winter boots.

            • MrGD

              I’ve been wearing a pair of winter dress(ish) boots from Pajar with my suits for the last couple years and, while I didn’t love them at first (I wear slim suits and the fur lining made them seem a bit bulky), they’ve broken in quite well. They’re very warm, waterproof and comfortable. I just looked at their site and the Othello-B is the closest to what I have. They’re based on the Plateau so you could probably go check them out in person.

    • asian_dapper

      I live in Edmonton and I feel your pain brother.
      I just put on my trusty Adidas clima-warm boots (I know, way to destroy a suited look) and bring to work whatever shoes I want to wear. At least you’ll still look dandy inside the office. Outside, not so much.
      To add, I recently purchased a rubber-soled Aldo leather wingtip boots that’s not so bad in the snow (as long as it’s not knee-deep), decent grip but also warm and I find myself using that more and more instead of the Adidas boots if its not too snowy. Or icy.

  • JoeFromTexas

    From the splash picture, and scrolling through the article, I almost thought you were gonna leave out Cowboy boots. Glad to see AlexFromTexas’ influence is not lost. And the link to one of my favorite articles, featuring the black suit and bolo with the brown boots. Don’t sleep on ropers either, for when the weather gets rough. You man Grayson had some nice ones in http://articlesofstyle.com/21718/weekend-layers-feat-grayson-knight/. And two more cents – python looks great, but it’ll flake off and fall apart before they ever get broken in, teju (common) or ringtail (less common) lizard is a much better bet for longevity.

  • http://www.TSBmen.com/ Dan Trepanier

    Those are SICK! Definitely one of those lifetime purchases. Just take good care of em; caps, shines, resoles, all of that…and they will pay you back in the long run ;)

    • cam

      thanks for the advice dan. btw, I’m going to pick up something from your s/s line as I’m pretty set w my cold weather gear. hopefully you’ll have some nice lightweight trousers to choose from. thx again!

      • TO

        How old are you cam? Must be nice being “set”!

  • Branas

    Nice article, and right on time! Was looking at adding some new boots to my arsenal.

    Btw typo at “Alpine Boots”, there’s a k in front of hiking. Don’t want anyone thinking these are for fashionable anti-semitism excursions…

    • http://www.TSBmen.com/ Dan Trepanier

      lol. Nice catch. Updated.

  • brauel

    Great article!
    Do you know the brand/make of th workboots you featured?

    • Matt

      Red wing iron ranger

      • http://www.TSBmen.com/ Dan Trepanier

        That is correct!

        • Todd

          No. 8111 in Amber Harness for you connoisseurs…