What Shoes To Wear During Winter Rain And Snow (If You Want Dry Feet)

Winter brings the rain and the cold, and most of the time, getting wet is unavoidable. Luckily, we have rain coats and weather-resistant parkas, but if you don’t pay attention to your footwear, you could end up with damp socks and shoes, which is no fun at all.

Funny thing is, I still see guys walking around in the rain with jeans, Vans, and a hoodie… which confuses me. Is your goal to absorb as much moisture as possible? It always comes down to dressing appropriately for every occasion, and canvas shoes and cotton hoodies don’t hold up well in a rainstorm.

Let’s focus on footwear, specifically. If you’re keeping it casual, here are some great shoe options for you to consider for your capsule wardrobe.

A Few Shoes Suitable For Snow, Rain, and Wet Weather

Here’s a selection of EG-approved shoes and boots that can withstand wet weather. We’re including a variety of styles here, with most of the casual end of the formality spectrum.

A. Thursday Statesman Dress Shoe

This shoe is built with a dressy template and work-boot-inspired construction. Since it’s a derby, not an oxford, the two design sensibilities come together smoothly. You can definitely wear this shoe with a suit on many occasions. If it’s slippery or rainy outside, no one would bat an eye. Ever versatile, it looks most natural in smart casual situations, especially with jeans, but can level up casual outfits.

B. Timberland White Ledge Mid Hiker Boot

This Hiker Boot is robust enough for hiking, but light and stylish enough to be a casual, urban shoe. I love how velvety the nubuck upper is. The multi-textured look is dynamic but not overly performance-forward or weirdly maximalist. Its agile and slip-resistant rubber sole does well in light to moderate rain, but don’t go jumping into any puddles. For that, we’ve got the Hunter Boot.

C. Hunter Original Boot

You have to have a true rain boot in your arsenal. It’s a must. Not only are these classics built to withstand the worst of wet weather, but they are aesthetically associated with a sort-of British country gentleman look.

D. Huckberry All-Weather Duck Boot

I love the classic LL Bean Boot (and it’s always worth looking into), but I find this remix of the duck boot from Huckberry is quite distinct. It’s a little sleeker, with a more streamlined silhouette.  It’s as all-terrain as any dry-to-wet boot, but can almost be styled like high-top sneakers.

E. Thursday Diplomat Arizona Adobe

This boot has a similar vibe to heritage Red Wing Boots (especially with that charming rubber outsole), but with modern sensibilities. It’s also not as bulky as some of the Red Wing Models. It’s ruggedly handsome, built with tough and beautifully oiled leather. Even more, it boasts Goodyear welting and a steel shank. This means you’ve got security on top of comfort, and waterproof resole-ability.

F. Taylor Stitch Suede Ranch Boot

There are few boots more versatile than a chelsea. The Sonoma Chelsea for example, is a good non-weather option, but this Ranch Boot is made from waterproof waxed suede, which matches the brawny aesthetic of the snow-friendly lugged sole. It’s definitely rugged, though the minimalistic look makes it highly adaptable.

G. Carhartt Ground Force Composite Toe

And speaking of ruggedness, you may sometimes need a really deep lugged work boot. And this is even if you aren’t in an industry that requires workwear. This boot from Carhartt can crunch through thick snow, and its composite toe adds extra protection. It’s still lighter than your average heavy-duty work boot though since it isn’t a full steel toe and its shank is nylon.

“What’s The Best Way To Wear These Boots?”

I recently got an email asking: What’s the best way to wear (these boots) with my pants?

Method #1: Pants over boots

The most obvious way would be to let your pant leg drape over your boots, which happens naturally with a straight leg pair of pants.

Method #2: The Right Amount of Cuff

If you have a slim or tapered pair (or even a straight pair that’s a bit long), you could cuff the pants so they’re sitting up a bit higher on the boot shaft.

The amount of cuffing depends on the kind of break you want in your pants. Sometimes you may need just one fold up, sometimes 2-3.

Method #3: Tuck Into Your Boots

If you’re wearing boots that allow it, and the weather calls for it, you may want to tuck your pants cuffs into your boots entirely. This will ensure you’ll stay dry. In this situation, what matters most is not arriving at your destination with wet pant legs.

To Cuff, Or Not To Cuff Your Jeans

If your cuff naturally drapes over the boot, then let it be. If your pants get wet, then start rolling them up! Adapt, my friends. Adapt.

And truthfully, so much of classic menswear is rooted in function, so garments that feel practical with your choice boot will likely look good too—or at least look natural.

Both duck boots and a flannel shirt are made to keep you warm, and they pair beautifully together. By the way, when you’re done here, check out our guide on plaid and flannel.

If you’re out and about on a rainy day, you may decide to tuck your pants into your Hunter boots. This may seem practicalist and anti-style, but the British countryside folk and old money set have been doing it for ages. Bring it all together with a quilted vest, button-down, a tweed jacket, and perhaps a flatcap if that’s your style.

Even more, a lot of hiking boots don’t have to be contextualized in an outdoorsy way if that isn’t your style. The streetwear crowd has been sporting Timberlands since the ‘90s, so you can definitely go more urban and less country.

Leather in wet weather

Here’s the thing. If you work in a more formal setting that requires you to wear leather dress shoes, they’ll be okay so long as you put shoe trees in them at the end of the day and let the leather rest. That’s very important. Shoe trees. Rest for a day.

And here’s how to weatherproof your leather shoes. We have a whole guide on the matter so that if you absolutely have to go out in the rain in inappropriate shoes, you’ll know how to at least up their resistance!

Clean Salt Off Your Leather Boots ASAP

One thing to watch out for, especially for you peeps in snow areas: salt on your leather shoes. Salt + leather shoes = sad face, big time. This is all the more reason to NOT wear your nice leather shoes when you’re commuting by foot.

If you absolutely must wear your leather shoes when braving the elements, it’s really important you treat your leather with care once you reach your destination. A simple wipe-off should suffice. Be thorough, however, because any stray slush or salt water will stain your shoes and getting that stain removed is a pain in the butt.

Also, this is another reason (if you haven’t yet been motivated) to polish your shoes regularly.

Conditioning and polishing the leather will help keep your shoes in tip-top shape and ready for whatever you throw at it. Think of it like moisturizing your skin after showering. If you don’t moisturize, you dry out, skin gets rough and cracked, etc. Your leather shoes work the same way.

Want a step-by-step solution for removing salt from your shoes? Check out this concise guide from Valet Magazine.

How To Not Slip and Fall In Wet and Icy Conditions

If you’re more concerned about your own safety—walking around on wet, icy, or snowy ground with leather soles is not very fun or sexy—then you have some alternatives.

One would be to take your leather-soled shoes to a cobbler and have a thin rubber layer added. Many places do this and it shouldn’t be tough to find a cobbler who knows what you’re asking for.

I’ve heard arguments for and against this method. Some say it’s perfectly fine and they haven’t experienced any problems. Others have said adding a rubber layer decreases the breathability of the leather and can trap in moisture which leads to rotting, curling of the rubber, and in general, ruins your shoes long term.

I’ll leave it up to you to do the research and decide whether or not this is a good solution for you.

Another option is to check out something like SWIMS, which are overshoes that help protect your leather from the elements. They also increase grip so you’re not slipping and sliding everywhere.

I think the best solution would be to own a pair of dress shoes with a rubber or combination rubber/leather sole that you use on rainy and wet days. The grippy rubber will keep you safe and minimize slippage as you walk around. Aesthetically, you want the same look as your other dress shoes. The only difference is that instead of a leather sole, you’ll have a rubber one.

An example of a combo sole is pictured above, from Cole Haan (these are a similar style) .

If you go the full rubber route, keep them for rainy day wear only. The leather sole adds a level of formality and sexiness you just can’t get with rubber. Keepin’ it real, yo.

That’s what we’re working with, gents

Hope this makes your rainy days a bit easier to deal with. What do you think? Any wet weather footwear favorites the EG community should know about?