What They Don’t Tell You About Getting Dressed in the Winter

Every winter I think to myself that finally, this is going to be the season I turn things around, that I figure out how to look chic through the winter. I am so hell-bent on figuring it out that I maintain zero qualms or hesitations about using the word “chic.” I flip through the lookbooks that land in my inbox and the runway photos that populate Vogue Runway and think to myself: Why did I give up last winter? There are so many great options out there! Just look at those silk pants, that trench coat — and what about that dress? This is it, Leandra. This is the season that we finally turn things around!

But it never sticks. I always forget until it’s freezing again that there is really no way around it. Dressing “well” in the winter (if, you know, you don’t work from home in satin kitten heels or a silk towel and you’re the kind of person who commutes to work by foot or public transport) is impossible. If this does not ring true for you, you must not live in a city like New York, which is a town remarkably distinct about its disdain for practical dressing. It has the ability to make you feel guilty for wearing snow boots!

Now that I am pregnant, the impossibility of dressing well through the winter is even more obvious because I have thus inoculated myself from the expectations of getting dressed at all. No, not dressed: ~DreSsEd!!!!!~ These days, I’m good for a pair of stretchy pants and a huge sweater, thick-ass socks and either a snow boot or sneakers and this — practical dressing — has really shone a light on all the things I never realized about the clothes I used to buy, but never really get to wear, for winter. Here is a comprehensive list of the myths that I used to believe.

1. Of course I will wear novelty tops. What else do I have going for me?

Here’s the problem: They don’t fit under coats. And particularly considering the trend wave we’re riding now, how the hell is a pair of sleeves bigger than two basketballs supposed to comfortably nestle themselves inside the armholes of a jacket. Can they? Should you expect them to? Don’t you worry about what will happen to the top if they’re smashed into a coat for too long?

2. Blazers are a tried and true form of layer that works.

Blazers obliterate my intentions once again: no matter how thin or thick, they just don’t fit inside winter coats. Sure, you can feign it, but it’s painful in that your mobility is severely compromised. You can barely bring your arm up to your face when you’re wearing a rigid layer under a coat. Also, I wonder, what’s the point of wearing a great blazer if no one, yourself included, can see it?

3. Winter is a great excuse to explore my style within the realm of midlength dresses and skirts.

There is a particular ratio ideally struck between a coat, whatever is covering your bottom half, and your shoes. Unfortunately, super long coats look awkward with midlength dresses or skirts if they’re not the same length, and where fabrics are concerned, the heaviness of your coat is disproportionate to the flimsiness of your skirt or dress. Short coats don’t keep your ass warm.

4. Silk is warm. I will wear a lot of silk.

Static, static, static. Have you ever tried to wear recreational non-pajama pajama pants with a sweater on a cold winter day? Follow up question if the answer is yes: Did all of the electric shocks incurred by the fabric combo light up your town?

5. I shall wear pumps with socks.

Camp socks? No. Flimsy socks? But will your foot stay in the pump?

6. I shall wear socks with sandals.

Cool in theory, but painful in action, particularly because the floors are always moist and your toes will get wet.

7. Winter is a compact time! I’ll wear flare and wide-legged pants that offer me additional height.

The truth is it’s a pain in the ass to get to wherever you are headed in fussy pants and heels and the floor is never dry. Your skin and lips and cuticles are — but the ground? Moist as can be, so the bottoms of those pants will get fuq’d. And you might slip.

8. This weather is a great excuse to wear cozy thick sweaters with all my favorite high-waist jeans!

So true in theory, but thick sweaters don’t tuck into high-waist jeans. They’re too thick. You can fake it, but it’s never the same as a tried and true, solid tuck.

9. I will wear many clutch bags.

What’s more elegant than a lady in a bell coat, holding her purse close to her heart? A reasonable question, but the answer is: avoiding hypothermia. You need your hands in your pockets lest you lose your fingers to the cold.

Homepage photo by Simon Chetrit; Feature photo by George Silk/The LIFE Picture Collection via Getty Images.

Leandra M. Cohen

Leandra M. Cohen is the founder of Man Repeller.

More from Archive