The Fits We Wear on Vacation

A low-stakes test kitchen for the clothes you bought bravely and then quietly feared.

The test kitchen.

Sometimes you want to go where nobody knows your name.

I enjoy being away, but the days and weeks leading up to a trip always make me feel like I left the stove on.

Naturally, I deal with this in the healthiest way possible.

I look at menus. I book spa treatments. Most of all, I shop.

I prep outfits for days that do not technically exist yet. Because if the fit is hard, maybe the sky cannot fall. I turn my wife into my personal fit pic photographer and painstakingly curate the rare Instagram dump, so a modest audience of people who did not ask can see the fruits of my angst.

Every trip comes with a business decision: am I the weather’s bitch, or is the weather mine?

I went to Asheville recently, and even though conditions were not ideal for my OL Welding Shirt, ALL SYSTEMS WERE GO.

In the monotony of the summer T-shirt and shorts cycle, I was determined to descend into the depths of my closet and wear the outfits I had been sculpting in my head while the stove was on. Even if that meant sweating through lunch, pretending seersucker was air conditioning, and immediately changing back into Baggies the moment the check hit the table.

Chefs do not put new dishes right on the menu. They burn them. They over-salt them. They realize the thing they thought was genius at midnight tastes like a cry for help in daylight.

Vacation does the same thing for clothes.

It gives you a place to stress test outfits before you roll them out at home. A small, low-stakes test kitchen where nobody knows the menu. Think of it like running a special. The shirt you keep moving around your closet, self-conscious about the crop. The pants you bought with confidence, then feared because of their silhouette. The fun pair of sunnies that are not quite ready for a group beach day.

A special, briefly on the menu.

We do not play dress-up on vacation. We give our bold purchases time to decant before pouring them for the regulars back home.

Wear the clothes you are usually too self-conscious to wear and do not explain the choices to anyone. Live in your forgotten garments for a few days and let them cook.

And if they work, they come home with you. Not as souvenirs. As starters.

The cruelest part is that when you finally put on the piece you have been mythologizing, you usually realize it worked the whole time. It worked before the trip. It works during the trip. And if you can remain bold long enough to unpack it, it will work again.

Worst-case scenario, the fit bricks on vacation. And if a fit bricks on vacation and no one is around to see it, did it really brick?

As nice as it is to walk into the same place every morning and have them start making your cortado before you say a word, sometimes you want something with whipped cream. You want to make a lil mess.

Being someplace new removes all the preconceived notions people have of you. Nobody knows your usual uniform. Nobody knows what counts as “a lot” for you. You get to manufacture a little fake aura, wear it around for a few days, and bring it back as lore for the boys at home.

That is the trick: you are not trying to live in eternal vacation fits. You are bringing back a little sauce for when the everyday starts tasting bland.

Snuggling up with some juicy tailoring and cosplaying in a hotel lobby bar with an olive-oil-washed martini is an extraordinary way to spend an afternoon. But the phone will eventually ring, and someone on the other end will be asking a question you have answered a million times.

The dream does not die with the vibration of a phone.

Fare Filone is Italian slang for playing hooky, which is an aggressively romantic way to describe not doing the thing you are supposed to be doing.

The art of cutting out early is not about going off the grid. It is not about “finding your beach.” Most of the time, it is smaller and dumber than that. Steal a little room back for yourself. Break routine without blowing up your life.

Add the extra layer even if you sweat through it. Smoke the cheeky cig. Buy the book even though you have piles of unread ones. Cut out early, even if you have to come back and hop on a call.

What’s the piece you’re packing because you’re too scared to debut it at home?

-SP