Keep Your Feet Dry: What shoes to wear in the rain and snow

by Barron Cuadro  |  in Accessories

In my little corner of the world, winter is here… and with winter comes the rain and cold.

I can’t complain too much since we San Franciscans don’t get the ridiculously freezing cold winters like some of you do with your snow and sleet and storms, but it still gets wet and dreary. You can’t help but cover up and rush from point A to point B when it’s miserable outside.

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.

Aaanyway, let’s just focus on shoes today. If you’re keeping it casual, here are some footwear options for you (click to enlarge):

A. Caterpillar Dougald (unavailable, similar): The folks at Caterpillar were nice enough to send me a pair of these to try out. They’re rugged and good looking, built like a work boot but with the looks of a casual brogue. The sole is rubber, which is great for walking on slippery surfaces. If it’s a light rain (as opposed to some crazy flash flooding), you’d be good with these.

B. Timberland Earthkeepers: I still have my classic boot from the days when I used to wear baggier jeans, and if I can remember to pull them out of the closet at my parents’ house, I’d wear them. If I had to start from scratch with Timberland, I’d pick up this pair.

C. UGG Hannen: These ain’t your usual sorority sister’s Uggs! Vibram sole, lined with sheepskin, and in a cordovan color (editor’s note: not necessarily made of cordovan leather, thanks to reader Andre), these boots look awesome and will keep you dry (not to mention warm and toasty). These are in a different league than the ubiquitous slip-on model worn by sloppy American college students nationwide. Just sayin.

D. <strong>Original Bean Boots from L.L. Bean[/earnist_link link_id="78331"]: These are my rainy day go-tos. I slip them on and go jump in puddles. Sometimes I splash K accidentally, but I don’t always tell her because she’d probably get mad. So yeah, they’re EG tested and approved!

E. Hunter Original Short Boot: If you’re ever caught in a downpour, have to wade in waters ankle-deep, or accidentally walk through large puddles, you’re covered as long as you have these on your feet.

Bootiquette: How do I wear these?

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

Sure, it may seem a little daunting. You’re accustomed to shoes ending at the ankle.

To be honest, there’s no right way, really. Well, there is… and that’s whatever keeps you the most dry.

Cuff up your denim, let them sit in between the boot’s tongue and back tab, tuck them in if you have to. What matters most is not arriving at your destination with wet pant legs.

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.

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.

De-saltify (huh?)

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.

Wipe down your leather shoes after walking through the snowy slush! – Click to tweet this!

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 de-salting (that’s not a word) your shoes? Check out this concise guide from Valet Magazine.

Staying in an upright position (a.k.a. not slipping and falling)

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.

Some people think this is super nerdy. Others (like myself) think they look kinda cool. I don’t yet own a pair, but I’m inclined to pick some up and try them out. I encourage you to do the same; feel free to report back to me for extra bonus points.

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? Let’s hear em in the comments.