"The thing about jackets is that you have to wear one or you will freeze to death and die."

How To Dress For Transitional Weather

I’ve sung the praises of rainy days before, but I’ll be honest because I trust and respect you: summer rain has shit on fall downpours.
Right now, it’s day 4013 of cloud, cold, and precipitation (with very intermittent breaks), and I am the autumn equivalent of a maniacally happy Princess Elsa building her ice castle in Frozen. My hair hasn’t expanded to the point of eclipsing all natural light, I can layer without my clothes sticking to me like Ross Geller’s leather pants, and I can bundle. And layer. Or both. (Usually both.) This, like Justin Timberlake says in The Social Network, is our time. And if it isn’t your time, I’m sorry. (You’re wrong, and you should feel ashamed.)
So to further celebrate the two months of glory (before winter’s reckoning), I’ve compiled a guide to dressing for transitional weather a.k.a the weather we’re experiencing right now a.k.a. rainy-ass days. They say to write about what you know. And because I don’t personally know Leonardo DiCaprio YET, I will write this.
1. You can never, ever have too many jackets
The thing about jackets is that you have to wear one or you will freeze to death and die. And, perhaps most importantly, you will also look completely out of your mind if you insist on wearing a T-shirt in a balmy 10-degree breeze. “I’m fine!” you will argue, praying you don’t pass out from being so cold. “It’s WARM!”
It is not, and we know it, and you know it, and we are all adults so why don’t you have a jacket? Do you know what serves as a jacket? Everything. An oversize plaid! An oversize military shirt! An old, vintage fur that your grandmother had! A Dickies’ work coat! Just like that acne commercial starring the guy who ate too many chocolate bars promises, there are solutions. And if you know how to work a Value Village, Goodwill, or sale rack, you will find many solutions to your lack-of-jacket conundrum, I promise. Some of them will feature jazzy French embellishments, like so:
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2. BUT, maybe invest in one (1) really great coat
Canada tries to destroy us from November to March. It rains, it snows, it hails, it winds, it chills, and last year I backed over a snowbank and had to kick snow out from underneath my car while lying on my side. Shit gets real, is what I’m saying. What should also get real: your coat situation. (Segue!) And while you may be told that the best coats cost hundreds and consist of goose down, note that isn’t actually true. Last week, I picked up a Gap parka jacket for $100 (regular $178) via a 40% sale, and SURPRISE SURPRISE it’s warm as hell. As far as I, a person who buys coats is concerned, $100 is reasonable for a coat because we’re not children and a coat can last for years. (And should! What the hell are you doing in your coat, anyway?) And this is coming from someone whose income depends solely on writing on the Internet, so if I can justify it, who can’t.
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3. Rain boots
Look: once in a while, I’m going to splurge, okay? Like, after I’ve waited for about five years, and tried on multiple pairs and said, “Nah, I mean . . . I have other boots, it’s okay” I am finally going to lay down the money and buy the goddamn Hunters I’ve thought about since seeing them for the first time in 2009. So recently, I did. And I am wearing them now, and it’s rained every day since I bought them, and I hope it rains every day hereafter because I am a monster. Of course, there’s more than one brand of rubber boots, and all of them will succeed at keeping your feet dry because that’s how rubber works. Just, for the love of all that is good, remember to wear thick socks with them because otherwise your feet will freeze and fall off. (Don’t question me I know everything.)
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4. The biggest sweater you can find
And I mean BIG. Like, you know those cute, fitted cardigans that exist at various chains? Not those. Maybe buy 40 of those and sew them together and then make a sleeve of the sweater I am talking about. To be honest, what I’m describing is available only at thrift stores, Value Villages, and via handmade gifts from your grandmother. It is made of wool, it is thick, it is heavy, it is long enough to almost be a dress. It is also available for about $5 if you play your cards right AND can function as a pullover jacket if you play your cards right (read: choose to wear it as a pullover jacket). You can also wear it to bed, then stay in it all the next day, and wear it to bed again the next night.
Not that I’ve done that or anything or plan on doing that tonight.
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5. Real socks, damn it (pictured above)
Real ones. Not any of this ankle shit. And I love a dress sock as much as the next person, but the last thing I need when it’s pouring rain and just-above-freezing is anything that isn’t going to give me the illusion that I’m warm. No offence, fancy sock designers, but do you know who’s going to see my fancy, completely un-warm chausettes? Nobody. Because on my way home from wherever I am coming from, I will have curled up in a restaurant and started to weep in my boots because life is unfair and my feet are cold—and cold feet are far worse than just being afraid to marry somebody for the rest of your natural life.
So: warm socks. Whether at Joe Fresh for $10 (a pack of two!) or at Roots for $10/pop. You’re not better than them. None of us are. We’re adults now, let’s be practical. I bought a toque because my hat was cold the other day, for heaven’s sake.
Go forth and buy. Then tell me about it.

1 Comment

  1. TheFunkyCrew
    October 23, 2014

    #3 – no need to splurge on overpriced Hunters 🙂 tons of options at places like Winners – I personally got a pair from Beyond the Rack 3 years ago, a Canadian brand “Kamik”, for a fraction of the price of fad-y hunters

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