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: 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.

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22 Responses

  1. Jurgen De Cleen on

    Great Article. You have shown some really nice boots! Also the items about wearing boots and how to care for them were really useful! Winter is coming here in Belgium! So before the cold came I bought a new pair of boots from BlueBox. Dark brown with a zip on the inner leg and an extra strap with buckle. This time I went for rubber soles, really for snowy and rainy conditions.

  2. Andre on

    Great article so thank you for that, however at $260 the UGG’s are “cordovan” color but I doubt they are cordovan leather, anyone know for sure?

    • Barron on

      Ugh, good point. I let that one slip. I’m pretty sure it’s cordovan color, not leather, otherwise those would probably be like $600. Correcting the above.

  3. Steven Earl on

    Boots have become an everyday shoe for me. Even with a suit (dress boots). I am from the Bay Area as well so there’s no snow or that much rain…but I still love wearing boots.

      • Jason on

        I ran a search of your site, but could not find any recommendations for boots comparable to your posts about dress shoes (which I found very helpful and ultimately guided me to buy a pair of florsheims [sp] on ebay this weekend). I know winter is winding down for some people, but a piece about boots would be great. Regards.

  4. DH in Canada on

    For rain, I don’t bother changing shoes. For winter snow, I have a pair of rubber sole Allen Edmonds chukkas. I had them polished regularly with shoe polish and later Urad, but that did nothing to prevent salt and water damage. I tried mink oil, but it dulls the leather and is difficult to buff off. I’ve settled on Granger Paste Wax, which is as water repellent and conditioning as mink oil but still leaves the leather reasonably shiny.

    I personally can’t stand lace ups, so I’ll also wear my various loafers with my Acton Urban rubber overshoes. It has the best winter traction of any winter shoe I’ve ever owned, are truly waterproof, and require zero maintenance. But boy, do I feel like a dork wearing them. I’m waiting for them to wear out before I try Swims.

    • Barron on

      Thanks for the details on your polish / conditioning experience. The overshoes you mentioned are interesting, because they look like an actual shoe, right? Those are the only types I’ve ever seen before Swims. I don’t mind them. Then again I’ve never worn them 🙂

  5. Joe S on

    When I get my shoes re-soled, I always ask for rubber on top of the leather. I have experienced the slipping on ice all too often.

  6. Ukmatty on

    Great article thanks for the advice. I’ve recently bought the ugg boots featured above and they are a lot redder than I thought they were (browner). Was wondering if anyone had advice of what to wear with these boots. My job doesn’t permit me to wear a suit to work so is just for casual/going out ideas. Thanks matt.

  7. Alex on

    Thanks Barron.

    I’m not sure what your experience has been with the Cole Haan soles pictured above, but my experience actually has been terrible with regards to rain. The issue is that there is a very slight gab between the rubber squares and the leather of the sole, inviting any water right up into the shoe. I sadly had a beautiful pair of cole haans with the combo soles ruined because I took them out in the rain. If I ever purchase another with the same soles, they will be strictly non-rainy day shoes.

  8. DH in Canada on

    Vinegar as a desalting solution works okay, but there’s a better product out there. And it’s not even sold by shoe stores. It’s a carnauba wax based automotive detailing spray.

    It’s more effective on salt than vinegar, and has excellent cleaning power, yet imparts a shine reasonably close to shoe cream for half the effort.

    Waterless wash and wax sprays are shinier but requires buffing, and takes just as long as shoe cream. Vinyl and rubber protectant is useless for cleaning and creates a dust attracting surface. Silicone sponges can impart a similar shine but it has no cleaning ability. Of course, if you want the most reflective polish, bees wax shoe polish works best.

  9. Dave New York on

    Can’t go wrong with any of these choices. I would say wear the Caterpillar Douglad out for date night, because they go a more stylish oxford look. The hunter boots are for those snowy days shoveling the driveway. B and C could be worn to work if done correctly, maybe with some cuffed fitted pants. The LL Bean Boots resemble Sorel boots, a winter staple.

  10. Connie on

    Hello, My daughter is a pet baither for a pet groomer. Her feet get wet and she gets horrible blisters all over her feet. She is only allowed to wear something all black, and needs something that will not be so hot on her feet that they crest their own moisture. She’s at risk of losing her job! Help please!