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Ask the Strategist: I Need Men’s Rain Boots That Aren’t Ugly

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In our advice column, Ask the Strategist, we take your most burning shopping questions and scour friends, call up experts, and draw from personal experience to answer them. As always, please comment with one of your own — we’re here to help.

Question: I need good snow or rain boots that aren’t ugly. I’ve been rocking the Cole Haan Chelsea boot that are waterproof, but I need something a little sturdier. Hunter had some nice ones, but they sold out of the good stuff too soon. Know of anything else?

This question came from a guy, so we decided to find fashionable Seattle Instagram dudes and stalk them until we uncovered their boots of choice.

That led us to an account called Seattle Gents and to Strath Shepard, creative director at Nordstrom and curator of rare books on photography, art, fashion, and design at Pacific Standard Books. After a deep stalkerish scroll, I found a pair of shoes he’s made a habit of photographing over the last year.

After asking around and zooming in on logos, I discovered that these are a pair of Red Wings, a century-old shoe company founded in Minnesota. It turns out the ones Shepard’s wearing are classic oxford’s, not boots, but the pair was actually inspired by Red Wing’s work boots and designed for people who might not need the support of a high-top. They’re still waterproof.

Classic Oxford
$250 at Red Wing Shoes

For the rain, though, we’d suggest going all in on the tall boot, what Red Wing calls the “Classic Moc.” The great thing about them is that they’re waterproof, but don’t actually look waterproof at all. Excellent for the days when it says it might rain, but never does and you don’t want to be caught in the horrifying state of wearing rubber shoes all day. They come in a few colors.

Red Wing ‘Roughneck’ Boot
$270 at Nordstrom

They’re also available at Amazon.

Red Wing Heritage Men’s Classic Moc 6” Boot
$270 at Amazon
Red Wing Chukka
Photo: afront
Red Wing Chukka Boot
$230 at Nordstrom

Then we did a little poking around what else Nordstrom, and presumably Shepard, is offering in terms of waterproof men’s boots. There’s the Red Wing chukka boot, which looks like a regular leather boot, but is also waterproof.

Samuel Hubbard Re-Boot Waterproof Gore-Tex Chukka Boot
$285 at Norstrom

Another chukka, this time by Samuel Hubbard and in black.

Trask boots
Photo: CAMERA1
Trask ‘Andrew Mid’ Apron Toe Boot
From $275 at Nordstrom

There’s this Trask, which is pretty similar to the Red Wing. It has a grippy sole and is made in England.

Now back to Seattle Gents, that menswear influencer Instagram. These Gents were all mostly dapper and not to be found wearing many rain boots, but I reached out to Endurance Weke, a blogger who goes by @CuratorOfCool and who’s featured on Gents. He wrote back with some of his favorite options.

Robert Wayne Thomas Lace-Up Zip Boot
$40 at Nordstrom Rack

“Being based in Seattle, the weather is mostly 65 percent rain during the year. With that said, most people wear some type of boots throughout the seasons,” he wrote. His first choice was a Robert Wayne lace-up. “On most melancholy, rainy days, this boot is perfect in this weather. The dark-brown color is perfect for those days were you feel like wearing all black, or that grunge vibe. By Thursday most people are already tired of the week, so you can wear this boot and throw on jeans and whatever sweatshirt on top and call it a day.”

Kenton Leather Pacer Boots
$248 at J.Crew

His second pair from J.Crew are actually pretty similar to the Red Wing’s. “This boot pays homage to the classic carpenter boot, so of course you know they’re durable. I would consider this the starter boot for anyone trying to see how it would look on them and those not really sure what kind of boot they’d go for first.”

Hunter Men’s Original Refined Chelsea Rain Boots
$116 at Bloomingdale’s

And lastly, I found a couple of other pairs that I thought worth throwing into the mix. First, these Hunter Chelseas that aren’t yet fully sold out.

Saks Fifth Avenue Collection Buckle Rubber Chelsea Boots
$278 at Saks Fifth Avenue

And a similar, more fashion-y pair by Saks.

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Ask the Strategist: I Need Rain Boots That Aren’t Ugly