Fashion

Dear Family Who Doesn't Understand My Style

How to navigate the "You paid what for that?" conversation.
IMAGE Getty
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Going home for the holidays is a special version of hell, coated in butter and sprinkled with sugar. It always sounds like a good idea, right? Go spend some time in a home you don’t have to clean, see the family who loves you unconditionally, and take a break from the reality that is soul-crushing work and Donald Trump’s America. But for the fashion inclined, the stress begins immediately. As a style editor, I’m only allowed to wear pieces that are black and overpriced. That’s it. It’s just part of the game. And I like my game, thank you very much. I spent the better part of my life figuring out my style, only to come back to the fucks who “love” me, just to find that they don’t agree with my choices. 

Some things I might hear: 

“Back in my day, you had to earn holes in your pants. And now you buy them ruined! Ridiculous.” 

“Did you know they sell those same designer bags for $20 on Canal Street? There’s no difference!” 

“I’ve been wearing the same sneakers for three years, and they still look fine. What’s the point of all these shoes?” 

And so on. It’s hard to keep your shit together when they come out the gate swinging. Your family is ready for a fight, and nothing gets you riled up faster than someone trashing your fits—especially when it’s coming from someone who doesn’t know what a ‘fit’ is. Get your shit together, Aunt Patty. I AM fashion. Here’s how to show them what’s up, no matter your style tribe.

1| The Tailored Peacock 


The problem: They think you’re overdressed. 

The truth: Jackets have pockets for pocket squares. Why would you wear a jacket without a pocket square like a goddamn psychopath? 

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The solution: Tell them you like Mad Men. It doesn’t matter that it’s been off the air for more than two years. They’ll see a suit, and think you want to be Don Draper. Be like Don: Lie to them. Then carefully readjust your four-in-hand.

***

2| The Prepster


The problem: They don’t get “trad.” 

The truth: It’s Thanksgiving, motherfuckers, and I’m wearing a button-down oxford cloth shirt under a cableknit sweater if I want to. These people wouldn’t understand a pair of sockless loafers if they hit them across the face. 

The solution: Find the one uncle who used to dress like you do now, just back when Ivy Style was a new thing. Win him over. (Beer helps. Whiskey helps even more.) Let him fight your fights for you. Enjoy your own whiskey.

***

3| The New Skater


The problem: They think you look like you walked off a mall parking lot. 

The truth: You kinda do. But, like, a fancy mall parking lot. Plus, crew socks and Vans Old Skools are life. 

The solution: Calmly explain that fashion works in cycles, and this is currently a dominant force in the industry. Plus, it’s comfy. And practical. If that doesn’t work? Do a kickflip.

***

4| The Sneakerhead


The problem: They believe you have too many unworn sneakers stored in their boxes. 

The truth: You have too many unworn sneakers stored in their boxes. But they’re valuable. And the ones you do wear are fire. 

The solution: Start talking about the secondary sneaker marketplace in minute detail. Explain the nuances of the hype cycle. Hope that pretty much everyone checks out of the conversation, but that your one aunt who works in futures decides that speculation is the same game no matter the commodity. Then see if she’ll finance your sneaker resale app.

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This story originally appeared on Esquire.com. Minor edits have been made by the Esquiremag.ph editors.

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Christine Flammia
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