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.

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

My closet has become a hope journal on hangers: full of crushes, delusions, and versions of myself I planned on becoming.

I want all of it, and somehow almost none of it wants me back.

I am, at my core, a dirty maximalist capitalist and proud of it. The thrill of finding that perfect item, the sales associate telling you, “those were made for you,” and the rush of adding to cart — it is the type of bad decision that briefly feels like self-improvement.

But when the tags are off and the return policy is voided, we face the reality of our overstuffed drawers and comically full closets. Here are the items I just can’t quit and the ones that represent the man I want to become.

The J.Crew Giant-Fit Oxford

Why I wear it too much:
This has been my most-worn piece of clothing by a mile. I like the fit. It’s always on sale.

In the interest of full journalistic transparency, I have six of these and am wearing the blue one as I type this. This shirt is my Linus blanket. I wear it with gym shorts and suits, and it never looks out of place.

Why I’m sick of it:
As the expression goes, there’s always someone tired of fucking her. Though this shirt would represent a major upgrade for anyone drowning in performance polos and gingham button-downs bought by moms, girlfriends, and wives, it has turned me into a one-trick pony.

Snuggled deep in the comfort of my slightly oversized oxford, I have lost sight of what really matters: getting off massive fits.

What I should wear instead:
Emily Dawn Long Jeff’s Shirt.

Jeff’s Shirt is the EDL piece that gets me going: personal story, great colorways, and enough detail to make my stack of oxfords look less like taste and more like a tic.

I could have been a coward and referred to the delicious Wythe Oxford that I also own in an abundance of colors, but when getting dressed, we must not take the path of least resistance.

I am not saying you need this shirt in every color. I am saying I bought one a few months ago, wore it a grand total of one time, and have been treating it like it belongs behind glass ever since. But dry cleaners exist for a reason. Live in your clothes, don’t just visit them.

Would I recommend it?

J.Crew Oxford: Overwhelmingly, yes. You should buy ONE of these shirts. Whenever I put in an order at J.Crew, I add one to the cart out of fear that one day they will stop making it. If I feel that strongly about a shirt I’m actively complaining about, that should tell you everything.

EDL Jeff’s Shirt: Yes. Pick one that feels approachably ambitious and start wearing it like you live in it.

UNIQLO Barrel Pants

Why I wear them too much:
There aren’t many better feelings than having pants that just fit. When you’re running behind in the morning, a grappling match with your top button is enough to push any sane person to the brink. That is why we all love pants with a little give.

These give you room to breathe without looking like you have fully surrendered to a forgiving waistband. The barrel leg gives you just enough of an “I do clothes” look in a room full of ABC dupes.

Why I’m sick of them:
When the day comes and you have to put on pants that do not stretch, you are in for the battle of your life. Your trusty wedding suit no longer clasping is not a surprise. It is a jolt of reality. The elastic has betrayed your tailoring.

NOT ALL OF YOUR PANTS SHOULD STRETCH.

Do not let your pants lull you into submission. I, like any other full-blown adult, need pants that do not negotiate. No drawstrings. No secret give. No quiet little waistband bailout plan.

Worse, any fashion-guy effect the barrel leg once had for me has worn off now that it has become part of my uniform.

What I should wear instead:
Casatlantic Tanger Trousers.

Call me Kurt Angle the way I wrestle with this top button. I have had these pants for a few years, and though I have very few notes on them, they have plenty of notes for me.

The leg is wide without looking silly, and they serve as a great base for anything from a T-shirt to a blazer. But I have been betrayed by drawstrings and elastic, and these do not always fit me the way they do in my hope journal.

The dream remains alive, even if the button currently disagrees.

The less punishing route: The Ralph Lauren Andrew Pant can usually be found on eBay for much less, for those who want accountability on a budget.

Would I recommend it?

UNIQLO Barrel Pants: Yes, but be careful not to fall for their trap. You are not shrinking; the pants are just negotiating.

Casatlantic Tanger Trousers: If they speak to you like they do to me, yes. Nothing holds you accountable like spending real money on pants that don’t give a fuck about your feelings.

adidas x Wales Bonner Karintha OG

Why I wear them too much:
I don’t buy sneakers often — a direct response to growing up in New York during the hypebeast era. After learning everything I could about sneakers in my younger years, I checked out sometime around the Galaxy Foams.

In sneakers, I look for ease without going full NPC. I have cycled through 990s, Sambas, Stan Smiths, and any other white sneaker trend you can think of, including an extended stay in a pair of Golden Goose sneakers that I wore through the soles. This pair is my next sacrifice.

Why I’m sick of them:
I’m sick of them because I shouldn’t be sick of them yet.

I was excited when I bought these. I am always looking for a white-ish sneaker, so I hunted down my size and ordered immediately. I love the way they look, and for the first few weeks, putting them on still felt special.

But as I lazily slip them on most mornings, I now greet them with an eye roll and a level of disdain a shoe this beautiful did not sign up for. I have turned them into a prison of my own creation.

What I should wear instead:
Gucci Horsebit 1953 loafers.

I was between two here. The Belgian Shoes Mr. Casual is probably my favorite piece of footwear I own. I wore them on my wedding day. But ultimately, my pick is the Gucci Horsebit 1953 loafer.

I bought my Horsebits as a reward for opening my first office, at a time when I really could not afford them. They made me feel like I was in charge, which is a dangerous amount of emotional responsibility to give a loafer.

The Horsebit is different from the Belgian. There is no IYKYK about it. Everyone knows. These are what I should be wearing when I want to dress up my self-imposed uniform, or when I need a kick in the ass to actually get dressed. To wear them is to show you care, and you want people to know.

Would I recommend it?

adidas x Wales Bonner Karintha OG: Yes. Watch your step. Anything this easy can go from “great everyday shoe” to “foot prison with better branding” very quickly.

Belgian Shoes Mr. Casual: Resounding yes. I love these. I wore them on my wedding day. They look great beat up, and sizing can get weird. Just a heads up.

Gucci Horsebit 1953: Yes. If you’re looking to splash out on timeless footwear, you could do a lot worse. I bought mine when I had no business buying them, and I still think they were worth it.

The Layer I Refuse to Wear

Why I keep doing it:
Day in and day out, I go from an air-conditioned car to an air-conditioned office and convince myself what I’m doing is enough.

The truth is, in my day-to-day life, a sneaker not everyone has and a little play with proportion is going above and beyond. It’s easy. It’s comfortable. And to the untrained eye, it probably looks like effort.

Why I’m sick of it:
A chore coat, a knit, even a belt. Something to turn clothes into a fit.

I keep putting on clothes without getting dressed. The bones are there, but I feel incomplete as I scurry from one climate-controlled area to another. Never having to remove a layer or undo a button, I have been swaddled into mid by the thermostat and automatic start.

I yearn to dress.

What I should wear instead:
Our Legacy Welding Shirt.

To know me is to see my Mr. Porter wishlist. This shirt held a residency on said list for the better part of a year. It is one of those rare wants that became a need. I planned outfits and envisioned a life with her, and when the most recent sale came, I pounced.

I regret to inform you the tags are still on.

As much as leather needs to be worn to find its final form, I neglect it, stowed away like Rapunzel in a garment bag in the back of my closet. This is not a break-in-case-of-emergency layer. It exists because sometimes the outfit needs to stop being convenient and start being dressed.

There is nothing lazy about it, which is why I can’t look it in the eyes.

Would I recommend it?

Our Legacy Welding Shirt: Yes, if it speaks to you. But this is not really about the shirt.

In a deeply unironic sense, I recommend shopping your closet. Give away or sell the stuff you know you are never going to wear again, then find the few things you have been too lazy, scared, or precious to wear and get a fit off.

The clothes are already there. The problem is us.

Comment the piece you have been too lazy to wear, then tag @farefilone in the fit pic when you finally stop being a coward.

-SP

Well, I tried running and it killed my dad… so I guess I’ll start a Substack.

Is there anything more embarrassing than new?

Wearing a pair of bright white sneakers in public for the first time. The sun shining on them. Blinding people as they drive by.

Last summer, I bought a white pair of Nike Cortez and walked them through the nearby park until the picture-day shine was gone, before wearing them anywhere that actually mattered.

As I struggled with my disappearing hair, I did what any sensible person would do: I got the buzz cut. Around the same time, Channing was riding around with Zoë on his pegs. Though I am sad to report I was not an exact clone, it worked.

People liked it.

But the first time you see people after a change, the attention you get far exceeds what is appropriate for a grown man. They all knew the embarrassing fact that I tried. That I was self-conscious about something.

This is the true embarrassment of new: putting yourself out there.

None of this has stopped me.

When you love silly little outfits — the name of my menswear group chat on IG — you can never stop searching for and ringing the shame bell on something new.

Recently, in my search for slutty silver jewelry, I came across Gottlob and bought a silver necklace.

I have never been one for necklaces outside of a cross at my baptism and a misguided era where I wore a rose gold Cuban trying to get in touch with my Staten Island roots. But I took a shot.

Then came the usual questions, including one of my employees asking me if it was a family heirloom because it just doesn’t feel like me.

Nevertheless, I prevailed. I overcame the shame of new and have a new daily driver.

Though I wish I could say that all of my risky purchases go off without a hitch, even the most coveted items sometimes fall flat.

After weeks of deliberating, I pulled the trigger on an awesome MFPEN sweater.

Unfortunately, it did not fit anywhere close to how I imagined. It would never see the light of day on my body, despite being something I thought was surely going to be a staple in my rotation.

It left my spirit deflated and my body inflated.

Sometimes the worst part about trying is trying on.

New was not always like this, though.

New used to be met with anticipation and promise.

In 2004, fresh off Kevin Garnett’s MVP season, Adidas blessed us with the KG1. I had to have them.

After a lifetime of wearing Shaqs and, at the time, uncool New Balances due to my mother’s insistence that I had a wide foot — a statement I think is her own version of Munchausen by proxy — the KG1s would be my back-to-school shoe.

Growing up in a working-class family, as you may know, the back-to-school shoe was a huge decision that would anchor my outfits for the foreseeable future.

Choosing the quilted white pair — before new white shoes made me want to crawl in a hole and die — was bold.

I was bold.

My obsession with clothing and what I wore came at a very young age, and though outwardly it ebbs and flows and I fall into a uniform like most others, the love remains the same.

That is what we will do here: explore that love with a few other things that I feel I have more authority on than others for no real reason other than I like how I do it.

I’ll tell you my size — probably only if you ask.

I’ll link you to things I think are good. I won’t get paid for it, and I’ll tell you what I paid.

I’ll do my best not to list the five best shoes to wear this summer or clothes you can wear from the office to the course to date night.

And if I’m talking out my ass, I’ll tell you upfront.

I will chase trends and regret it. I’ll tell you when the fit bricked.

Example: the Tom Ford ballet flats I have been wrestling with for the past few weeks, which my wife has made clear are hideous and should remain between me, Tom Ford, and my group chat. I can promise you that if I could find a 14, they would be purchased and regretted.

Now for the embarrassment: the public shame of putting yourself out there, most likely to abandon it and have it remain online forever in the graveyard of fitness-journey accounts, cooking accounts, and dog accounts.

But why not give it a shot?

This may end up being the next KG1.

I would ask you to subscribe, but I am not as bold as I once was.

— SP