Q&A: Warm and Waterproof Winter Shoes for Him

December 17th, 2008

Q:  What are some good winter shoes that are warm, comfortable to walk in, semi-waterproof (unlike canvas converse sneakers that just soak up the snow), affordable, and fashionable - both his and hers.

Quoddy Trail Grizzly Boots
Pictured: Grizzly Boots | $320 at Quoddy Trail.  Other more affordable options: Suede MacAlister boots | $135 at J Crew, and Clark’s Desert Boots | $89 at Zappos.

A: I’ll address the “his” part of this question.  The “bad weather shoes” problem is much simpler if you’re not a white collar worker.  Without a doubt, the first pair of bad weather boots I’d recommend are by Quoddy, makers of high quality bad weather shoes.  As you can tell, however, they are for people who experience a few feet of snow in the winter.

Desert boots are another viable option if you live in a place with a less harsh winter.  Clark’s desert boots have always been around, but nowadays you can find stylish desert boots everywhere from J. Crew and the GAP (via Pierre Hardy) to high end retailers like Tom Ford.  The beauty of desert boots is that you can wear them while walking around the city as well; it’s a bit harder to “urbanize” those rugged Quoddy boots.

If you’re a working man, you have it a bit harder.  You have to wear dress shoes to the office, unless you work in a creative industry.  Certainly, you can wear galoshes, but that option is more practical than stylish (even though Esquire endorses it).  If you live in the city, where the streets are a bit more groomed (e.g. less snow on the sidewalks), you can try wearing dress boots, but again, at a formal, conservative type office, I’m not sure that would fly.  If you do decide to wear dress shoes or dress boots, do wear ones with rubber soles.  The snow and slush will wreck havoc on your leather soles.  If you absolutely must wear leather soled dress shoes to the office, do not wear them outside; instead, change into them at the office.

Last words?  Please feel free to beat up your shoes; in fact, I encourage you to wear them in.  A lot.  Tom Ford ran a series of ads a year or so ago in which a man in alligator shoes was walking through the mud.  I love this; “beat up the pretty things,” as they say.  Buy high quality things and wear them out.  This kind of nonchalance is the essence of American style, so embrace it.

UPDATE from Colleen Geary for women’s shoes: The tricky thing about winter shoes is that they’re often ruined by winter conditions - water, salt, ice and mud. I’d recommend purchasing a very inexpensive but good looking fake leather boot from Target or Walmart that can be worn with pants or skirts. Choose a pair with clean lines so that it’s inexpensiveness is not readily apparent. “Indulge” in a pair of black or brown leather boots that you love and can be worn for occasions or when the weather is not inclement. In Utah, you should have enough occasions to warrant two pairs of boots.

Have a great tip about great bad weather shoes–both his and hers?  Share it with us in the comments!

Entry Filed under: Men,Men's,Q&A,Shopping Guide

7 Comments Add your own

  • 1. Sal  |  December 17th, 2008 at 1:16 pm

    My husband bought a pair of Doc Marten slip-on mocs specifically for winter – they’re clunky enough that he doesn’t mind ruining them, but just dressy enough to pass muster at the office.

  • 2. deka  |  December 17th, 2008 at 6:10 pm

    i love them!
    too bad my boyfriend would never wear them

  • 3. Trisha  |  December 18th, 2008 at 12:06 am

    Doc Marten slip-on mocs are a great choice–thanks for sharing, Sal!

  • 4. Tom  |  December 18th, 2008 at 5:07 pm

    I agree a distressed pair of shoes can look good. Obviously Jcrew agrees as well — their catalogs show distressed shoes aplenty. I think they sometimes put a pair of shoes through a ringer before putting it in front of the camera.

    But you wouldn’t wear a distressed pair of shoes at a conservative office right? — in fact, a lot of us shine our shoes on a semi-regular basis — and I’m wondering … Just how casual does the setting have to be for a distressed pair of shoes to be appropriate? Would you wear a pair to a nice dinner party? Would you ever wear a pair with a suit — not at a conservative office, but maybe at say a little less formal wedding?

  • 5. John  |  December 19th, 2008 at 6:43 pm

    Some are more affordable than others, but all look nice (from men.style.com) and all are made for the outdoors (re: snow):



    Right, don’t wear a pair of worn in shoes to a conservative office. Those shoes should be in good conditioned and shined regularly, so you’re doing well.

    Worn in shoes in general are a) more casual than not worn in shoes and b) one of those things in style that is more about attitude than anything.

    Well worn shoes create a “too cool to care” look (don’t mean that in a bad way). If you’re wearing Brioni with a sharp crease in your trousers, you’re better off wearing well kept shoes.

    If you’re wearing an unstructured jacket and jeans (or even a casual suit, say from J. Crew), you can go for the worn in shoes.

    The idea is that you want to present a cohesive “image” – a formal suit but casual, beat up shoes (even though they may be casual, beat up dress shoes) doesn’t fit together that well.

    Also, the “feeling” i get from worn in shoes is different. Wear them while walking around Soho or at the park; don’t wear them at galas, museum openings, or to Per Se.

    Finally, a word about predistressed anything (but especially shoes): I don’t like them. At all. Worn in shoes, to me, is more about attitude. When you buy a brand new pair of worn in dress shoes, it’s like they designer is trying to manufacture that attitude, and it doesn’t work for me.

    Buy high quality things and wear them in yourself. Beat up the pretty things, as they say.

  • 6. Tom  |  January 1st, 2009 at 2:19 pm

    Thanks, John. You’re the best.

  • 7. Anonymous  |  January 12th, 2009 at 2:29 pm

    Blundstone boots are a great unisex solution to the snowy sidewalks / white collar office conundrum.

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