Five Winter Boot Options for Men

March 13th, 2011

Blizzards are no time for boat shoes, drivers, canvas sneakers, loafers, etc. From late December to early March, I probably wear boots about 75% of the time.

A boot is not just a boot, there are different styles for different occasions and it’s important to have the right pairs in your winter rotation.

Here, five different styles, with five different aesthetics.

    1. Rugged/Alpine

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    For those unexpected blizards that can bring 13 inches of snow overnight, you need at least one pair of trudging-through-the-sh-t boots. I lace these things up and don’t have to think twice about what I’m steeping in or on – they’re insulated, completely waterproof and have a virtually indestructible beefy rubber sole.

    Where I wore this: Class – “History of Menswear”

    Bonus Tip: Red laces? Why not? Winter outfits are generally darker and more muted, allowing an unepected dash of red to be the sole “pop” (no pun intended). Matching stripe on gloves was a coincidence.

    Bonus Tip II: Looking for a timeless but inexpensive outerwear piece? Official Navy-issued peacoats are abundant in vintage stores. Try-on a handful of them until you find a proper fit (or at least one that needs minimal alterations). For $50-$100 these classic built-to-last  jackets are a no-brainer.

    Bonus Tip III: An accesorry, particularly a lapel pin, can be made of just about anything. It’s a great place to be innovative and add a personal touch. More on unique/unusual acceorries (including the anticapated lapel acceorries) coming soon. (We can only work so fast! We are juggling several projects at once).

    • Brown leather alpine boots by Alife
    • Navy peacoat Vintage naval issue
    • Grey micro-check washed cotton shirt by Steven Alan
    • White striped cardigan by Rag&Bone
    • “New Standard” Raw denim jeans by APC
    • Grey suede gloves by Thom Browne
    • “Roman Coin” brooge Vintage

    2. Wingtip Brogue

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    A leather brogue wingtip is very versatile because it looks both dressy and casual at the same time. These are one of my favorite pairs of boots. They can be dressed up (see here) or down (see here).

    Where I wore this: A meeting with potential buyers (samples in duffle bag).

    Bonus Tip: When it’s wet out sometimes I tuck my pant hems into my boots to keep them dry. Once you walk inside, simply pull them out and let them fall over the laces.

    3. Boat Boot

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    The comfort and casual aesthetic of boat shoes but for off-summer  months. Genius. Just remember these are casual shoes, not meant to be dressed up.

    Also keep in mind they are unlined leather – so if there’s snow on the ground, you might want to think about thick wool socks.

    Where I wore this: A friend’s apartment, then college basketball game at Madison Square Garden

    Bonus Tip: Burgundy, or it’s deeper brother “oxblood”, is a versatile and style-forward footwear color that doesn’t stray too far from traditional.

    • Burgundy boat boots by Sperry
    • Tan moleskin peacoat by Filippa K
    • Navy washed cotton shirt by Steven Alan
    • Olive cargo pants from Army/Navy surplus store

    4. Suede Chukka

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    A chukka is another boot that can easily be dressed up or down. The simple and clean silhouette works as great with slim flannel trousers as it does with straight raw denim.

    Where I wore this: Art show in upper manhattan

    Bonus Tip: Everybody has suede chukkas in tan, brown and black. Try a more unexpected (but still neutral) color like forest green, burgundy or navy blue.

    Bonus Tip II: Leather soles are generally stiffer and slimmer – which makes shoes dressier and sharper in shape. Rubber or crepe soles (like Clark’s famous “desert boots”, for example) are unmistakably more casual in nature – and thus work better with jeans than suits.

    Bonus Tip III: A suede boot is a little counter-intuitive. They’re boots that you can’t wear in the rain or snow. This makes them a “luxury” type of item. With that said, a suede chukka should be well-made and sharp, not casual and sloppy.

    5. Captoe Lace-Up

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    What do you do when someone steals your favorite pair of Ralph Lauren leather captoe boots (see way back, here)? You upgrade them with a bad-ass pair of handmade Italian oxbloods.

    These, in my opinion, are close to the “perfect” boot. Oxblood leather, 8″ lace-up, brogue captoe, rubber sole, perfect last shape (notice the toe box – not square but not round).

    Where I wore this: Vintage shopping.

    Bonus Tip: Colors are starting to lighten up as Spring approaches and we begin seeing sunny days again.

    Bonus Tip II: Transitional times are coming – soon it will be time to start mixing fabrics and colors (light blue unlined cotton trench over wide-wale corduroy vest and oxford shirt, for example).

    • Oxblood boots by Scarpe di Bianco
    • Light blue cotton trench by Burberry Prorsum
    • Grey cotton shirt by Onassis
    • Navy corduroy vest
    • Slim washed denim jeans by Polo Ralph Lauren

    Thanks for reading.

    Yours in style,

    Dan Trepanier

     

    Photography by Alex Crawford.

    • Josh

      Hey, love the boots in style #1, the Alife boots? Where do I find these mythical beasts?

    • Anonymous

      wow.. i like the article.

    • Dani

      Sorry. Wasn’t paying too much attention to the shoes (I’m sure they’re lovely) but Look #4 is on the dot.

      Simply Dashing…

      http://chicalarusse.com/

    • Paul

      so, why can’t me wear high boots? The pictures of pants tucked into ankle high boots is just stupid, rather wear a nice pair of leather two toned boots and look like I didn’t just get my pants stuck in my shoes. Can some designer make a style of leather boots for men? Unless we can just get a pair of 10 women’s flat boots and call it even!

    • Jonathan Charles

      I’m not sure where to look for pants like that, do you have any tips/locations?

      I was also thinking of wearing a wool peacoat in a very similar colour vs the coat you have shown. Would that work?

      Thanks.

    • Charity H

      I’m a female, however I like your tip of the chukka boot in other off-the-beaten-path colors. I have a traditional pair of chocolate brown chukkas with a round toe (as opposed to narrow), and also a pair of kate spade chukkas (approx 8 years old, they never go out of style!) in baby blue suede with off-white laces and soles. I’ve never seen anyone else with these shoes and they’re great for color-blocking or matching! Loving the oxblood leather of those boots as well. I always enjoy your blog! Keep posting great photos and styles!

    • Swashbuckler

      So many people are opposed to the boot-tuck. I love it!

      I only wish i could pull it off as suavely as you!
      Looks fantastic, Dan!

    • kevin

      wow..cool boots i love alpine with cool red laces.

    • Jon

      I love about 99% of the posts that you do and this one is no different. My only beef is with the “boot tuck.” That $@!% is wack! But everything else is great! Keep up the good work!

    • Alxist

      I am actually more interested in that trenchcoat in “5- Oxblood Captoe Lace-Up” than the boots. Any ideas about the designer of that?

    • Joey Dee

      Sometimes i wish for the weather so i can get me some boots, then i go out on weekend and work on tan, ha ! Great work as always. Last photo just speaks, so clean ! When ya get big and larger than life, we can all say, he gave us dressing points !

      All the best to your endeavors
      Joey Dee

    • Shoes de Pierre

      Great post man, I really like the direction this site is taking. Keep it up, it must be a hell of a lot of work!

      http://shoesdepierre.blogspot.com/

    • Arsene

      Styles are so clean and classy yet so friggin functional… (bowing down).

      I’ve been meaning to get the sperry boot all winter but somehow never got around to it. With spring around the corner I just went and opted for a sharp chelsea boot. Would love to see your take on the chelsea.

      You are an inspiration dude

    • cardion

      Dude, I just really don’t even know what to say about your style. I mean the sh** is sick.

      I do have a question. If I were to get a pair of boots made (like those in the last pic), how much I would be looking to spend around?

      • Albert

        Custom Scarpe’s are going to run you in the $800 range.

        • http://www.thestyleblogger.com SB

          Those boots in particular retail for $1095.

          Thanks for reading,
          SB

    • naples9

      saw someone post ab artofgear.com. it is real fresh. yall look

      http://www.artofgear.com/

    • Dave

      Last look is awesome.

    • Bartek

      DAAAAN!!!!

      We need more of your posts..

      I am addicted :)

      • http://www.thestyleblogger.com SB

        haha. Thanks!

        In truth, I wish I had more time to blog (and thus post more often). Between juggling several projects (working on the collection, design school, consulting work, etc) the blog only gets a small percentage of my time & effort :/

        This is still just the begining for this site, though.

        Best,
        Dan

    • Matt F

      great post, 2, 4 and 5 are great, love how you get dressier/work appropriate stuff into interesting looking outfits in ways I would never have thought about.

    • obell

      Nice styles, love it all. Cool gear is an art, we collect it

      http://www.artofgear.com/

    • Wojohn

      Maybe it’s because I’m from the South, but I would love to see L.L. Bean’s Duck Boots in your second boots posting.

      • http://www.thestyleblogger.com SB

        Don’t want to give anything away, but be sure to stay tuned ;)

        Best,
        SB

    • Tom

      Great timing! I don’t know about elsewhere, but it’s likely we’ll still get snow once more in Wisconsin. I ordered boots like the ones in look one, and they just arrived today. Thanks as always.

      • http://www.thestyleblogger.com SB

        Don’t be fooled, the winter – nor the cold weather – is certainly not over.

        Thx for reading,
        SB

    • JMRouse

      PS boots are some of my favorite and those oxblood’s are killer. It’s already hot here, so I didn’t get much time to pull off the winter looks.

      • http://www.thestyleblogger.com SB

        Tough to time the posts because readers are from all over (last month we had readers from 104 countries). More than I could name probably.

        Cheers brother,
        SB

      • Gabriel

        I’m kind of new to buying shoes for girls. She is 5’1″ so what’s the rule with the boot legnth? should i keep it short or long? Also what are some good brands out there for rain boots? I know about Hunter and Chooka any others you may recommend that is durable, cheap, yet fashionable? Thanks

    • Lou

      Hey
      The Oxblood Captoe Lace-Up, how can I get one of those??
      I’m so obsessed with these

      • http://www.thestyleblogger.com SB

        Click on the link in the captions under the picture – it will direct you to the Scarpe di Bianco website.

        -SB

        • Ole

          What is the price range of the Scarpe di Bianco boots? They look fantastic!

    • schuyler

      if that blue trench isn’t fresh- I don’t know what is.

      Nice work.

      • http://www.thestyleblogger.com SB

        Hey Schuyler! Long time no see, i hope all is well.

    • JK Ferguson

      Loving the High Topsiders. The weather here in the UK is starting to break into a warm Spring and can’t wait to break out the lighter footwear! My boots have had an absolute run around this winter.

      http://www.urbanpreparatory.blogspot.com

      • http://www.thestyleblogger.com SB

        Good call, the hightopsiders are great transitional boots.

        Cheers,
        SB

    • DCRob

      Love the Paul Smith wingtips..I respect your 2nd look, the unbuttoned collar to the untucked shirt, works perfect with the worn in boots. As for the first look, the Browne gloves dominate the look IMO, and that ain’t not bad!

      Cheers

      • http://www.thestyleblogger.com SB

        Thx brother

    • d knott

      I’M SURE YOU HAVE HEARD THIS BEFORE AND I AM COMPELLED TO SAY IT AGAIN…YOU ARE ONE OF THE BEST DRESSED DUDES AROUND. YOU REALLY HAVE ME STEPPING UP MY STYLE GAME. MOST PEOPLE CAN ROCK WITH ONE LOOK AND NAIL IT BUT YOUR DIVERSITY IS TOO SICK, LOOKING VERY COMFORTABLE NAVIGATING BETWEEN LOOKS. AND YOUR ATTENTION TO DETAIL IS UNCANNY YET EFFORTLESS. I STAYED AWAY FROM THE DRESSED UP (I.E. GROWN UP) LOOKS FOR A WHILE BECAUSE IT SEEMED SO…BLAND AND BORING AND CORPORATE. YOUR SITE GAVE ME A WHOLE NOTHER TAKE ON IT AND ACTUALLY MAKES IT EXCITING. WHILE I STILL LOVE MY JEANS AND T SHIRT WITH VINTAGE SNEAKERS AND SHADES AND HAVE A WHOLE NEW APPRECIATION FOR THIS KIND OF STYLE. YOU’VE HELPED PULL ME FROM STREETWEAR TO MENSWEAR. MY GIRL FRIEND THANKS YOU. LOL
      GOT TO GIVE RESPECT WHERE ITS DUE.

      • sincere

        Amen Bro.
        SB is a prophet to men’s fashion.

      • S.

        AMEN!

        • Rich

          haha agreed!

      • http://www.thestyleblogger.com SB

        hah

        THANKS!

        Really appreciate all the compliments and support. Makes me want to work harder. I wish I had more time to blog! Plenty more to come.

        -SB

    • Garth

      Definitely on of your best posts. Looking to pick up a trench for the spring, any ideas to get a slim fitting one on the cheap?

      • http://www.thestyleblogger.com SB

        It’s funny – sometimes I’ll be hesitant about publishing a post of look because I don’t think it’s good enough – then I pull the trigger and readers are calling it their favorite yet.

        As far as the slim inexpensive trench, start by looking at the following: H&M, Uniqlo, Topman, JCrew, Club Monaco, United Colors of Benneton, LL Bean signature, Land’s End Canvas

        You should be able to find something there.

        Cheers,
        SB

    • Stone Hudson

      Please stop tucking your pants into your boots every chance you get.

      • http://www.thestyleblogger.com SB

        If it’s not for you, don’t replicate it.

        Thanks for reading.

    • Really Now

      Always love the way you look away at the camera. Very professional and a natural. Did you ever model? You look like you have been doing this for a while. Also love the picture by the garage. Very original.

      • http://www.thestyleblogger.com SB

        Thanks. I’ve never done any modeling worth talking about (until starting this), but I guess I have been doing this for a little while now. Alex also makes it very easy and can make just about anyone look good (even me).

        -SB

    • Bosun

      love winter so much, winter fashion and footwear trumps anything summer has to offer in my personal opinion. In fact my recent blog post see’s me let rip on summer.

      Much love from the U.K

      http://thetastelevel.blogspot.com/

      • http://www.thestyleblogger.com SB

        Agreed – although I’ve recently picked up some pretty wicked Spring/Summer pieces.

        Good luck with your blog.

        -SB

    • alan m.

      Very impressive. Love the churchs in look 4. churchs makes the best shoes

    • Kevin

      Nice post, but I must agree with David…a little late to bring this now!!

      • http://www.thestyleblogger.com SB

        Depends on where you are writing from I guess.
        We have readers from 100+ countries, all with different climates.

        Best,
        SB

    • David

      Little late for the winter footwear, don’t you think?

      • http://www.thestyleblogger.com SB

        Depends on where you are writing from I guess. We have readers from 100+ countries, all with different climates.

        Best,
        SB

    • Ariel…

      Amazing post as usual, just one question. What are the Vintage ”Roman Coin” brooge on your Peacoat? I think that’s an amazingly innovative accessory…

      • http://www.thestyleblogger.com SB

        Good eye. More on this coming soon! (post on unusual/innovative/personal accessories).

        Cheers,
        SB

    • ciara

      quick question. is the navy corduroy blazer in look 4 part of the suit that your navy corduroy waistcoat belongs to? Great production as always.

      • http://www.thestyleblogger.com SB

        Yup they are both part of a 3-piece.

        Thanks for reading,
        SB

    • Dan L.

      I love those wingtips. Are there more affordable boots in that style? I haven’t been able to find anything cheaper than the 350-500 price range…

    • Amirul

      I have been keeping my eye on those chukka boots. Thinking if it was office appropriate. Now I know. Off to the stores.

      • http://www.thestyleblogger.com SB

        Don’t forget to remind the salesperson about my commission! haha

        Thanks for reading,
        SB

    • KLEE

      4th look….too good..

      • http://www.thestyleblogger.com SB

        Interestingly probably my least favorite of the bunch. To each his own!

    • Jen Smith

      The first pair of boots has to be my fav. I do like that style with a bit more of a chunky shoe string….Anywho, what about your jacket in the last picture, does it have an ombre effect on it? If so its pretty awesome!

      jen
      http://blankwhiteframes.blogspot.com

      • Jeff – Style for Modern Men

        hi,

        yes it does. Fadings are one of Burberry’s main patterns these last seasons.

        regards,
        Jeff from http://www.styleformodernmen.com

    • Andrejs

      Like!

      • http://www.thestyleblogger.com SB

        Click the button! :)

    • Jeff – Style for Men

      Nice boots, they’re definitely a must have for winter !

      I especially like the 80s US Jump Boots (Corcoran’s) that you can find in army surplus too.

      Too bad new high-tech fabrics have replaced the good old leather.

      Jeff, from Paris
      http://www.styleformodernmen.com

    • Zulhilmi Rahman

      Like it, period!

    • mikaela

      awesome dan!

      • http://www.thestyleblogger.com SB

        Thanks Mik!