The Untenable Misery of Shoe Shopping for New England Weather

Buying footwear for Massachusetts’ unpredictable weather is about as fun as a broken leg. Bring back local shoe stores!

Illustration by Zohar Lazar

WHEN YOU GROW UP in Massachusetts, you grow up with weather. Sure, every place has it, but not like here. We got the best. It’s freezing. Now it’s hot. Now it’s snowing. Now it’s raindrops that hurt. Hey, look at that foliage. Totally pissah.

We like to think we’re hearty, stoic types. Maybe the first. Definitely not the second. We looooooove to talk about weather, specifically what we do to beat it, like freezing bed sheets and sticking ice cubes down our pants to survive three days in July. Or how in winter, we shovel for 45 minutes and use a deck chair to save our spot until the thaw. Yeah, it’s called the Land for Furniture Exchange. Know the law, you out-of-state jackass.

But even more than talking about weather, what we really just like is to watch weather from our couches.

I was one of those people. At one point in my life, weather was never more than a mild inconvenience when it wasn’t a source of pure wonder. Heavy rain? So cleansing. Snowstorm? So peaceful. Let the flakes fall. Go, flakes, go. In the morning, I didn’t mind shoveling my driveway. I got to be outside, and tossing snow into my neighbor’s yard made me feel rugged. Sorry—more rugged. And when I came back in, I could take off my tough boots, sit, and revel in my ruggedness.

Then things shifted.

I became a homeowner and had land that needed tending, and 10 years in, I haven’t found the charm of tending land. Premortgage, I’d see leaves and think, “Love that orange.” Now? “Those are gonna fall. Eff me.” You’d think I’d stop saying to my wife on a late Sunday afternoon in October, “I can bang this out in 30.” Nope. Two hours later, I’m trying to squeeze 12 bags into my garage before I go back inside and hope that by morning a new batch hasn’t fallen. Those prayers are always unanswered.

Snow falls, too, and has to be removed, so I go out and do it because, unfortunately, as of now, there’s nothing that will set it on fire. (Hint, hint, MIT.) Oh, but before I can clear my small—but still not small enough—driveway, I have to break through the wall those good town plow drivers have erected and create an opening wide enough so my children can get to school and learn. (Can I stop my ruggedness? Not even if I tried.)

Yet that’s not the warmest feeling on a cold morning. That comes when I look down the street, and what do I see? Could it be? Yes, yes, it’s the town plow drivers returning to rebuild that wall. I’d clap, but my fingers have been numb for 20 minutes. But make no mistake; I love that you’re here, town plow drivers, regardless of what my face might convey. (That’s numb as well.) Please, clip my basketball hoop while you’re at it. No need to waste the trip.

Still, my weather-attitude adjustment wasn’t complete until…

I got a dog.

HE’S GREAT. In fact, he’s the best listener in the house. The problem? Now I have to walk and stand in whatever’s going on outside on his schedule, not mine, and certainly not the weather’s. I thought that I was prepared. I owned a coat and boots. Used them outside year after year. Thought they were effective, but apparently, they only work for going from house to car and car to building, not house to street, street to path, path to field. Wait for 30 minutes. Repeat later when it’s dark.

The bigger problem is that I don’t ski or play golf, so I don’t have the ridiculous clothing that people put on when the snow and rain start to blow instead of just saying, “This is stupid. I’m going inside.” So instead, I’ve stocked up on lots of random items—warm jackets, rain jackets, and wind jackets. Jackets with pockets. Walking pants with pockets. And rain pants with, oh yeah, pockets.

Like any good New Englander, I can bitch and moan about the weather pretty well, but I know where I live and what comes with it. I can take freezing temps and scorchas and be fine. The one thing that I can’t handle? Rain. I hate rain. I hate wet. I hate wet rain. The only thing in its favor is it waters the grass, so I don’t have to, and that’s all that’s on the plus side.

In the other column? It cancels baseball games. (We could stop right there.) It reveals where the leaks are in my house. It reminds me that we still don’t know where our umbrella is. It creates puddles. It gets my socks wet. It gets my dog wet. It creates mud. It gets my socks muddy. It gets my dog muddy. It will invariably get a book wet, causing the pages to crinkle and never lie fl at ever, ever again, ending reading as we know it. Boo, rain.

Still, the real problem with rain is rain boots. I haven’t owned a pair since I was nine, but a dog changes people. I needed some. I listened to a friend who swore by a style that’s extremely popular around these parts. That person was wrong, and I hate my boots, and now I hate that person.

What I really hate is that I choked on the purchase. I know that I love anything pull-on for the easy-on, easy-off. Did I get that? Of course not. The pair I bought, I’ll acknowledge they keep the water out, but they have laces—strike one—laces that are slick and refuse to stay tied. Strike two.

When I try to cinch them down, the sewed-in tongue digs into my ankle, making a rain walk come with a slight limp. Strike three. The material might possibly soften up, but I don’t want to invest any more time in them to find out. Strike four. Oh, and they’re indestructible, so they’ll forever mock me from my back entryway. Strike five.

In fact, shoes are at the root of my weather issues. I’m facing too many scenarios. I might be walking. I might be running. I might be standing. I might be going uphill. I might be going down. It could be rocky. It could be cold. It could be snowy. It could be high snow. It could be low snow. It could be icy. It could be slushy. It could be rainy. It could be cold and rainy. It could be warm and rainy. And I don’t have that much room in that same back entryway for the requisite shoes. But mostly, my problem boils down to the fact that there isn’t a shoe store within 20 miles of me.

Bottom line: New England weather bad. Online shoe shopping worse.

STILL, since I need boots, I go online because that’s where all the boots are, and the Internet is open late at night, which is seemingly the only time I’m free for more than five minutes. For all the “convenience,” the process is still somewhat lacking, to be kind. Really, for something that needs to fit and be comfortable, let’s have the process go something like: Search. Buy. Ship. Try on. Send back. Apparently, I’m no longer an 11. Wait four days. Try on again. Apparently not a 10 and a half, either. Send back.

This can go on as long as you want, particularly if you live five minutes from a Whole Foods, also known as your friendly Amazon drop-off location. But I don’t have the endurance, and by pair three, it’s “9W? Close enough.”

I’m not a complicated guy. I just want to get a pair of shoes and be done in less than an afternoon. Mostly, the thing I want, the thing I need, is limits. The Internet’s promise of an endless bounty ruins me. Steve, just give it five more minutes. You’re getting sooooo close. We promise. Try changing your filters again because you know you’ll find the perfect pair, even though you know you won’t. All you’ll find is less sleep. Stop? You can’t. (Cue evil laugh.)

And still no shoes. I could always buy five pairs and send the four back that don’t work, but that makes a dumb process dumber. It’s using too many resources, too much packaging, and degrading the environment. Plus, I know that I probably wouldn’t even send them back. Success is also incumbent on suddenly knowing how to tell if a shoe fits, which has never been taught in school (ahem, Department of Education). Like with many things, we go with what we know or what we think we know. And we all think we know how big our shoes are because they’ve always been that big. The problem? “You have a foot size, not a shoe size,” says Adam Farber, a fifth-generation shoe salesperson and owner of Mark Adrian Shoes in Gloucester. More than that, it’s always changing. The number is just something a company puts on the box. It’s not a personalized note. We’re left to guess, and we guess badly.

The answer must be to bring back shoe stores. I understand that CD shops and newspaper stands are gone because we’ve gone digital. But feet? We’re most likely to still have them in 30 years. Boston Mayor Michelle Wu, this is your next great initiative. We’re supposedly a world-class walking city without places to get the main walking equipment? This cannot stand.

But Project Insole isn’t gonna happen. I have no business acumen. I don’t pick stocks, and I’m not developing the next non-dairy milk sensation. (I say quinoa.) Yet even I know that if more neighborhood shoe stores could exist, they’d exist.

So, Mayor Wu, go to Plan B and reinvigorate the industry by reaching across the Charles to MIT. Tell them to shelve the set-snow-on-fire project for now and develop some tech that would let me put my feet up against my computer screen, and it would know everything about them: length, width, arches, ankle sensitivity.

When I get on a site of an online retailer, it would only show me shoes that fit. I couldn’t look at anything else, and if I looked at any pair for a sixth time, I would automatically purchase it with no option of return.

This idea is exciting. This idea is the future. This idea would get everyone walking tall and proud for miles and miles without any blisters. This idea could get me to not just stop hating weather but also to embrace it, all parts of it—the burning-hot car seats, the wind that blows icy snow into my face. And yes, even the rain. Boston, the forecast is in. It says love is in the air. It’s time to make this happen and make it happen soon.

I got a dog to walk.

First published in the print edition of the August 2023 issue with the headline, “Let’s Give Shoe Shopping the Boot.”