Sneakers are for sneaking
December 31, 2009 7:41 AM   Subscribe

Seeking advice on attractive men's shoes for winter wear to work. Dapper gentlemen, how do you combine weather-proof shoes with formal business wear and not look like a rube?

It's winter here in Boston, and snow/sleet/rain/frozen urine is everywhere. In clement weather, I wear my dress shoes on my way to work--but they're expensive, and I don't want to ruin them. In the past, I've worn waterproof Merrells to work, but I think wearing, essentially, sneakers with a suit looks all kinds of awful.

I'd like to find shoes that can keep me dry on the way to work but don't look dumb with business formal pants. I'm sartorially adventurous--so if the best option is bright yellow wellies with a suit and trenchcoat, I'm game. But I'm not particularly interested in wearing something of the sneaker variety, or a clunky cheap shoe.

Does anyone have a recommendation for a shoe that will fit the bill?
posted by Admiral Haddock to Clothing, Beauty, & Fashion (16 answers total) 4 users marked this as a favorite
I buy cheap, sacrificial dress shoes that don't look too bad from a place like overstock. I then coat them in waterproofing stuff, and switch back to my good shoes when I am safely away from the salt.
posted by 517 at 7:47 AM on December 31, 2009 [2 favorites]

I change shoes when I get to the office.

Alternately you could buy overshoes.
posted by Pollomacho at 8:07 AM on December 31, 2009 [3 favorites]

Best answer: I generally wear ankle-height zip up boots, that are either insulated or I put in winter insoles for them (which make a big difference in warmth, trust me). They look stylish enough and since my pants cover the top of the boot they look just like slightly more casual dress shoes. They're usually leather and I also waterproof them as best I can.

I still think that if you're that sartorially conscious, keeping a pair of good dress shoes at work is the best option, but if you're a travellin' man, then that might not be possible.

Here are some examples of what I'm talking about: 1, 2, or 3. The third one looks to be clearly needing the winter insoles option for warmth, but the other two are probably warmer, but look less stylish. Fashion or comfort, the age-old dilemma.
posted by dnesan at 8:15 AM on December 31, 2009

Best answer: I also keep a pair of nice shoes in the office and change into these whenever I arrive. Even if your shoes are multiple levels of weatherproof, you are quite likely to get all kinds of salt and detritus on them given the frequency with which the DPW salts and sands the streets during Noreaster season. Even the best looking shoes will look like Mother Nature vomited all over them on your way in.

My current winter wasteland work footwear is the Bankers Frick boot from John Fluevog with the leather treated with some neatsfoot oil for weatherproofing. The sole provides good traction in the snow and ice, and the boot itself provides some added insulation in the cold, protection from those inevitable moments when you step ankle deep into a snow pile. Also, with dress pants, to the casual observer it generally looks like you're just wearing a loafer with a monk strap
posted by bl1nk at 8:17 AM on December 31, 2009

If you're mostly sticking around the office all day can you leave some nicer shoes at work and change when you get there? I do this, though for different reasons (and my work shoes aren't that nice)
posted by ghharr at 8:19 AM on December 31, 2009

I'm with Pollomacho. Change shoes at the office or try galoshes.
posted by cheapskatebay at 8:22 AM on December 31, 2009

Response by poster: To be clear, I fully expect to change shoes when I get to the office. I am looking for a handsome way to get to the office. Because I am a dandy.

My concern with "disposable" dress shoes is that they might not keep my precious tootsies dry, even if I slather the shoes with waterproofer. Also, I don't love the idea of disposable shoes in the first place, having gone through many a pair already.

I already have galoshes for drizzly days (though Pollomacho's link is to a species of overshoe I've never seen before--looks pretty tough!). I like the idea, but if it's really nasty out, I don't want to entrust, say, a $350 pair of shoes to the protection of a $19 dollar overshoe.

Thanks to all so far--some of those links look promising. Warm is probably good too! As I look out my window, it is snowing again.
posted by Admiral Haddock at 8:28 AM on December 31, 2009

Response by poster: On re-reading, I see that it was not terribly clear at all. Apologies. Again, I am solely (geddit?!?) looking for shoes that would look good with business attire as I walk to work (it's about a mile) in the rain, sleet, snow; once I get to the office, I'll change into my work shoes.

A boot of some sort is probably in order. But while duck boots might keep me warm and dry, they'd look dumb with a suit.

Yes, Vanity, thy name is Haddock--but I can't help but feel someone has figured out a way to keep dry and look stylish.
posted by Admiral Haddock at 8:37 AM on December 31, 2009

Best answer: You want to search a site like for shoes with Gore-tex. You'll pay a pretty penny, but Gore-tex will keep you totally, absoloutely dry.

Here's a couple of quick results:

Geox Londra (plain toe)

Geox Londara (fancy toe)
posted by anastasiav at 8:54 AM on December 31, 2009

Best answer: Gentlemen wear rubbers. Overshoes are, and have been the norm for protecting dress shoes since the day they were invented. They are classy, practical, and easily shoved into a briefcase or overcoat pocket upon arrival.
posted by Gungho at 8:59 AM on December 31, 2009 [1 favorite]

I should clarify, none of the shoes above is insulated, just waterproof. It looks like the Berlin also comes in an ankle-high boot, which could be useful for stepping in puddles and whatnot.

Anything that is also insulated (Thinsulate, Primaloft, etc) is also going to have a much "clunkier" less of a dress boot look. I'd just go up a size and wear heavy socks.
posted by anastasiav at 8:59 AM on December 31, 2009

I bought a pair of waterproof ("walk-dry") Rockports around Thanksgiving. Since then, my feet have stayed quite dry (living in a very wet place). (I do often wear thick wool army-boot-socks underneath which may help.) The previous pair I had were not water-resistant but stayed, if not new-looking, then not-close-to-ready-for-retirement for quite a long time. A good friend was astounded that he had to put regular effort and elbow-grease into keeping his everyday-office shoes looking good, and mine looked better with no effort. Both pairs had a pretty brief break-in period, and the last stayed comfy and cushy for quite a long time. I think they were $90-100 RRP, but at the time all the department stores had generous percentages knocked off.
posted by K.P. at 10:17 AM on December 31, 2009

Sketchers makes some plainer styles, which work well as all-weather shoes.
posted by Citrus at 10:53 AM on December 31, 2009

Best answer: Men’s Dress Shoes for Cold Weather has some suggestions.
posted by sentient at 11:16 AM on December 31, 2009

Best answer: The Fleuvog boot soles are basically tyre-tread, but there are less "booty" styles which don't look too chunky.

I'd like to recommend something along the lines of the classic Aussie boot -- RM Williams would be the toppermost and best suited for formalwear, though I love my Rossis -- because they're pull-on, pull-off, but I'm not convinced that the elastic copes well with a northeastern winter, especially if you're dealing with above-the-ankle slush.

So, Chelsea boots.
posted by holgate at 12:34 PM on December 31, 2009 [1 favorite]

I'm with Gungho. Why not trust your $350 shoes to a $19 overshoe? Plenty of well-dressed men do, and I used to when I had to wear a suit through New York winters. As long as you periodically check your overshoe for tears or cracks, there's no reason to believe the rubbers will fail to protect your dress shoes from (1) water and (2) road salt and (3) frozen urine (??).
posted by hhc5 at 1:23 PM on December 31, 2009 [1 favorite]

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