The Back to School Guide for Guys Who Aren’t Going Back to School

Motion to make September 1 the new January 1. Do I have a second?

January is objectively terrible for reinvention. It’s cold. It gets dark at 4:30. Everyone is trying to stop drinking and start eating chia seeds or whatever. January feels forced. September, on the other hand, has always felt like the actual beginning of something. There’s change in the air.

Just because you’re not going back to school doesn’t mean you can’t act like you are. September is the perfect excuse to refresh your adult life. Reorganize. Get inspired. Move some furniture around. Listen to new albums. Buy a jacket. Read something that isn’t on your phone.

September is for “sharpening our pencils,” so to speak.

Here’s your syllabus. You don’t have to call me Professor. But I won’t stop you either.

Let’s begin with the soundtrack of your September. Because good music makes everything else on this syllabus better. From school drop-off commutes (for you Cool Dads out there) to background music while you cook dinner, these are the new albums I’ve had on regular rotation lately.

The opening track alone is enough to get you fired up about whatever comes next. It happened to come on during a recent trip to Puerto Vallarta, right as I landed at PVR, so maybe I’m giving it some extra credit. But I don’t think so.

I recently saw Kacey Musgraves live, which only further confirmed something I already knew. She’s the country queen of Millennials. At one point in the concert, she ascended from stage via this giant disco-ball throne shaped like a pair of nuts. Yes. Those kind of nuts. “It takes some big balls to do what I do up here,” she said while buckling into the seat of it. Then, “This is what happens when no one tells me ‘no.'”

I rest my case, your honor.

Plus, Midland opened the show. Another great new album to add to this stack.

The Killers frontman strikes again. I’ll forever love Flowers for his Warren Zevon cover, but this record gives me another reason. It’s stripped back, a little twangy, and easy to live with. The kind of album you can chuck on at any time.

This is a perfect album for commuting. To work. To pick up your kids from school. To walk to your local cafe. You want to be on the go with this album.

For working-from-home days when you need enough energy to keep things moving. Your head will bop. Your fingers will type a little faster. You’ll catch a flow while listening to this one.

Dinner music. Specifically, the part of dinner where the onions are in the pan, you’ve poured yourself something to drink, and you briefly feel like you’re in a rom-com.

For when you want to feel a little… bad. But in a good way.

This is what you put on when you’re walking around the park alone. Or feeling lonely on a business trip. Headphones required.

September dressing is the best. You’re not sweating through a t-shirt, and you don’t need a parka yet. For a few glorious weeks, nearly every piece of clothing you own is theoretically available to you.

Take advantage.

This is the annual return of the overshirt.

Something like Elk Head Clothing’s denim overshirt can function as a jacket in the morning and get tossed over the back of a chair by lunch. Signature Innovation Group’s Loom Woven Jacket (me pictured in it above) does the same job with a little more structure.

The point isn’t to start dressing for November in September. It’s to have a few extra layers you’re actually excited to put on.

You’re not enrolled anywhere. Doesn’t mean you can’t be inspired by the hypothetical uniform.

Rugby shirts, varsity-inspired knits, cardigans, collegiate stripes. Heritage athletic clothing feels especially right this time of year. Elk Head’s Heritage Stripe Rugby Jersey (me pictured in it above) scratches the old-school athletic itch without making you look like you’re headed to practice. Bode’s Double-Breasted Cardigan takes the idea several tax brackets further.

Call it adult varsity.

If summer belongs to linen, early fall belongs to suede.

You don’t need much of it. In fact, you probably shouldn’t have much of it. But one good suede jacket can make jeans and a T-shirt look like you thought about them considerably longer than you did.

Baracuta’s Roughout Suede Track Jacket is exactly the kind of thing I’m talking about.

I love sneakers. You love sneakers. September is a good time to remember other shoes exist.

A chunky pair of Paraboot Reims loafers gives jeans, chinos, and cords a little more intention. SeaVees’ Landing Boat Shoe occupies that useful territory between sneaker and proper shoe. And if you’re ready to lean all the way into fall, Tecovas’ Dean boots (me pictured in them above) are my favorites.

Back-to-school season used to come with an entirely new schedule. New teachers. New classrooms. New notebooks. New people. Adult life rarely hands you a reset that cleanly. So you’re going to have to do it on your own. Mix up your routine. Take up a new hobby. Build your own syllabus.

Some ideas to get you going…

Write Some Letters

Not emails. Not texts. Letters. Like with a paper and pen.

Buy stationery you like. Find a pen that makes you want to use it. Write to your parents. An old friend. Someone you haven’t properly thanked. A person who moved away.

The beauty of a letter is that absolutely nobody is expecting one. That makes receiving one feel disproportionately meaningful. So your letter doesn’t even have to be that good.

Rearrange a Room or Your Closet

You probably don’t need new furniture. You might just be bored with where the furniture currently is.

Move the chair. Turn the desk. Swap the art between two rooms. Take something off a wall and leave the space blank for a while.

There’s something strangely satisfying about waking up the next morning and briefly forgetting where you are.

Take a Class You Don’t Need

This is the closest we’re getting to actual back-to-school homework.

Take a ceramics class. Learn basic woodworking. Sign up for a cooking workshop. Learn to develop film. Figure out how to sharpen a knife properly. Sign up for one of those Master Class videos.

The important part is that the skill has absolutely nothing to do with your job.

You spent enough years learning things because somebody told you they’d be useful someday. Learn something actually useful to your current life.

September is a great reading month. It’s kind of moody, the air starts feeling like dark lit. But you don’t have to change your personality to become a serious reader. Just someone who spends an hour with a book instead of spending that same hour reading half a New Yorker article, checking Instagram, looking up an actor on IMDb, reading about that actor’s divorce, checking the weather, and somehow ending up watching a video of a raccoon washing grapes.

There will not be a test. Nobody is checking whether you finished the book, bought the loafers, listened to every album, or mailed a letter. That’s the nice thing about back to school season when you’re not actually going back to school. You get to pick the curriculum.

So take September as a permission slip to start something. Wear something different. Read something good. Move the couch. Put on an album. Cook dinner. Buy a notebook. It’s time for a refresh.

Happy New Year, Cool readers. Happy September 1. Class dismissed.