Like anything else, getting dressed is a skill, a muscle, or whatever term is currently trending in the manosphere. The point is, you have to do it a fuckton.
The lights shine brightest at weddings, parties, and restaurants with no overhead lighting. But if you want to play well when the lights are on, you have to go into business for yourself when nobody asked you to.
That means coffee runs. Dog walks. Grocery stores. Family parties where there’s a real chance you end up on your aunt’s Facebook — or, in my case, my mother-in-law’s — with no “do you like this one?” before it gets posted for mass consumption.
There have been plenty of times when my lazy “no one is going to see me” outfit has turned into online humiliation: tagged at a family party, looking like a stranger to myself.
There is a line we toe as people who really do this: do I look true to this, or new to this?
The stakes could not be lower.
You intentionally slip on a pair of Belgian loafers because the dog needs to go out, and someone notices. You take your perfectly thrashed Stone Cold tee out for a beer. You catch some rando looking at it with envy, and you ride that high into a bigger fit.
This is not a call to wear your opera pumps to Whole Foods. But the frozen food section is a launch pad.
It is where you break out the new shoes. Maybe the jeans you’re not quite ready to hard launch on a date. For me, it is usually a vintage tee I overpaid for that will never have the manners for the office, dinner, or any place you have to shower before going.
These outfits are one notch above proof of life.
They should not look like you put a ton of thought into them. They should look like your closet has no misses in it. Everything is so dialed that even your worst grab off the chair has a pulse.
These are the fits your kids are going to post in 20 years with the caption, “How did my dad pull my mom?” There you are, fitted as fuck, eating ice cream or holding court at happy hour post-beach.
Reliable bottoms, something relaxed up top that does not blob you out, maybe one loud or unfamiliar item you are letting decant around clothes with familiar notes.
Go high-low. Gym shorts with casual loafers. Swim trunks with something a little unhinged up top. A new jacket over a uniform that has already paid rent.
Accessories do a lot of the dirty work here. A well-patinaed hat, some good bling, handsome socks, cool sunnies, or a belt with some bite.
The trick is to look dialed, not deranged.
Most people only dress for the ball drop. They look completely lost during the countdown.
Find the clothes you love and live in them. Let them get coffee, pick up the item you forgot, and stick to you in the passenger seat on a hot day.
A wedding is easy pickings. Everyone looks good in a suit, and even better in a tux, as long as the fit is half decent. A vacation is a cakewalk. You empty the chamber. A reservation gives you permission to break out your fancy-boy clothes.
If you wait until your number is called, you are going to look like an imposter in your Sunday best — starched, standing like you owe your outfit money.
Singles score runs too.
Thursday, I’m teaching small ball. Subscribe if you want the cheat sheet.
-SP
The errands fits are always the most fun, bend the rules. Keep getting shots up. Thanks for the reminder, FF 🫡
What’s the piece in your closet that always gets you on base?