A Rain Boot Roundtable

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Few categories of shoes are more polarizing than rain boots. Some people swear by them whenever the ground is a little bit wet; others will wear a pair of canvas sneakers during a thunderstorm without thinking twice.

Then there’s the fact that rain boots are a difficult purchase to pull the trigger on, because unless you live in a place that rains often, you’re only going to wear them a few times a year, max. That kicks rain boots out of the “essentials” category and bumps them into “optional.”

And when you do wear them, rain boots are only serve a purpose for a small part of your day — when it’s raining, and when you’re outside in it — and at no other time. Are they even necessary? Do you even care?!

Below, three Racked editors — Julia Rubin, executive editor; Cam Wolf, menswear editor; and Cory Baldwin, shopping editor — debate the pros and cons of rain boots. Should you own some? Or are they just the dumbest shoe? I’m Tiffany Yannetta, our shopping/cruise director, and I’ll be moderating.

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Tiffany: Hello, and welcome to the rain boot roundtable. My general opinion, to kick us off, is that I think an all-weather shoe is important, but I'm not sold that it needs to be a rain boot. Let's begin with Cam, who is pro-rain boot.

Cam: I like what you're saying about an all-purpose shoe, it's very important to have one. An all-weather shoe can solve all the weather problems at once — and so why can't that shoe be a rain boot?

Cory: I've got a disagreement with that because rain boots are fine for the rain, but they are absolutely not snow boots.

Cam: I wear my rain boots in the snow with a heavy pair of socks, and I'm perfectly warm and dry.

Cory: I'm happy that that works for you, but I don't think we should recommend that people purchase rain boots for this purpose. Especially because they're hideous, which I think Julia can speak to a little more.

Julia: They are HIDEOUS. They're too high, they cut your leg off at a weird place. When rendered in rubber, the shape is exceedingly disgusting.

Cory: They're floppy, I will add.

Julia: Or too stiff! You never look at someone and think, "You look really good in that pair of rain boots." Oh, you know what it is? They don't conform to your leg.

Tiffany: The way a leather boot would?

Julia: Yes! You're literally in these rubber buckets, and no one looks good in rubber buckets.

Cory: My legs stick out of the top in a weird way that makes me look like I have mammoth calves. Hunter boots were so cool when I was in high school, I wanted a pair so bad. My mom and my sister had pairs — I tried to steal from both of them — and they just looked terrible on me. This could be why I'm biased against rain boots.

Cam: Wait — can we just stop really quick? Because I want to set a baseline. What boots are we talking about? When you're thinking of a rain boot, what’s the image in your head?

Photo: Getty Images

Tiffany: Cam, define rain boot.

Cam: Rain boots are duck boots, that's what I think of when I think about rain boots.

Julia: Wow, this whole time we've been arguing in parallel universes. A rain boot looks like a Hunter boot. A wellie. We’re talking the tall, typical rubber boot.

Tiffany: Duck boots, though — I always think of them for the snow.

Cory: Duck boots are snow boots, I say this as someone from New Hampshire, very close to Maine. Duck boots are for snow.

Cam: Why would they be for snow?

Julia and Cory: They just are!

Cam: What do you mean, they just are?

Cory: They're not rain boots.

Julia: They are a known snow boot.

Cory: There's that whole thing that they sell out before snow season every year.

Julia: Oh my god, Cam.

Tiffany: I think we all agree that rain boots are terrible, but snow boots are good?

Cory: Maybe we can all just agree that we really like the L.L.Bean duck boots? Actually, you know what, Cam, I'll give you this: They are half rain boot, half snow boot.

Cam: What makes it a snow boot?

Tiffany: The sole is more rugged. It seems that the three women in this room think wellies are rain boots, and the one man thinks a duck boot is a rain boot. Cam, what would your opinion be of a wellie?

Cam: I think that they can be cute.

Cory: On a lady, or on a man, or either?

Cam: On a lady.

Tiffany: What about as a man? Would you ever wear them?

Cam: I don't see a lot of men wearing wellies.

Cory: I've definitely seen men in rubber rain boots, and it's a terrible look. I want to know more about you thinking they're cute on women, though. What kind of outfit are we talking?

Tiffany: Oh my god, we're talking about Cam's beautiful girlfriend, Chloe, in, like, a big sweater, with her hair done.

Cam: And tights or —

Tiffany: Leggings?

Cam: Yes, that's the exact outfit.

Julia: That only looks good if you're tall like Chloe and also down to wear leggings! I am five foot tall, and I'm never trying to wear leggings.

Cory: I'm 5'2” and I do wear leggings, but if I wear those boots, I look so stupid in them.

Julia: Yes, I look super dumb, like you've squished my body.

Cory: Now, how do you all feel about the short version of rain boots? Because those exist, too; Hunter even makes a pair that's half lace-up, in the style of those L.L.Bean ones, but all rubber.

Tiffany: When they are shorter, they're loose at the ankle and rain gets inside. That's really stupid! Remember when Loeffler Randall made those little black rain booties that were really popular though? They literally looked like ankle boots.

Cory: Yeah, I've seen Chelsea boots that are rubber. What I usually do is wear Doc Martens that I've waterproofed. I recently got stuck in the rain walking home, about a half-mile in pouring rain, and I was wearing regular leather shoes. I was miserable, soaked through to the bone. It took two entire days for my shoes to dry out! So while I do see the need for a waterproof shoe, I'm not convinced it needs to be made of rubber.

Julia: Yes! I wear a pair of leather Converse high-tops in the rain. There's a serrated rubber tread on them. The leather is thick and worn and totally fine to get wet. Treated leather!

Cory: And can we all agree that those shoes that are made of rubber, trying to be rain shoes but in different styles — like the high heel rain boots — are terrible?

Julia: So stupid. I hate them so much.

Tiffany: They just look like a matte, gross leather.

Cory: What's the man's take?

Cam: I hate shoes that are trying to look like other shoes, just as a general rule. One of my biggest pet peeves is formal shoes that try to be athletic.

Julia: An imposter rain boot is even worse.

Cory: Any rubber rain boot sucks.

Julia: Any rubber shoe sucks. We haven't talked about how hot a rubber shoe is.

Tiffany: A rubber shoe is so hot. You're baking.

Cory: Here's the real problem: It's hot when you're wearing them in the summer, and your legs get sweaty, but if you're wearing them in the cold, I’m pretty sure rubber is conductive and it makes your feet freezing.

Julia: You also have a real lack of mobility.

Cory: Trying to run through a foot of snow in tall rubber rain boots — I've actually done this — it doesn't work.

Tiffany: Same, and it gets in the boot!

Julia: You need some limb articulation.

Cam: Guys, I just want to point out that the L.L.Bean boot is categorized under rain boot on its site.

Cory: Do they also categorize it under a snow boot?

Cam: I really hope that they don't… Fuck! Why is it there for both?

Tiffany: Well, that’s a perfect place to end then.

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Watch: The history of Dr. Martens