Why let the kids have all the fun? It’s back to school time. Which also means it’s the dog days of summer, and while autumn is just around the corner, it sure doesn’t feel like it is. So while this is shameless rationalization for shopping (and really, there are a ton of reasons not to spend your hard earned cash) it still seems like a bit of fun worth having. Below you’ll find some of the most common back-to-school items translated into potential pick-ups for the grown up guy who has an eye for style. Now if you’ll excuse me, I need to get back to writing my what-I-did-on-my-summer-vacation theme.

Backpack —> Briefcase

Backpacks might be convenient, but they’re just never gonna be as professional looking as a briefcase. Look for something that’s well made from leather, canvas, or ballistic nylon, doesn’t shout in terms of style, and comes with top grab handles AND a shoulder strap for longer treks.

New Sneakers —> New Shoes (sneakers count too)

My times have changed. Now, kids can’t have their sneakers clean enough. Back in my day you’d take those bright white, new sneakers, and head RIGHT out into the back yard to rub dirt on them. Yes really. No, I don’t know why. Anyway, don’t do that with any new footwear purchase. Dress shoes or sneakers. No faux dirtying up please. Those wholecuts above? Those are the new Allen Edmonds Mackenzie. And you can win them here on this very site next week.

Textbooks —> Style Books

In case you’re at the point where you’d like to fill out your bookshelf with something other than “intro to bio-chem.” LOTS of options out there. From coffee table style books (like A Man and his Watch) to timeless classics like Alan Flusser’s Dressing the Man. Then there’s our own Start Here page. It’s not a book. Or even an e-book. It’s just a part of this site. It’s basically our playbook. And it’s free.

New “Nice” Clothes —> New Nice Clothes!

Remember when your folks or Grandma would drag you to JC Penney or Kohl’s to buy you itchy, ill fitting, ugly clothes for school that somehow got labeled as “nice”? I’m convinced that’s where many men developed the (wrong) idea that dressing “nice” is irritating and uncomfortable. In fact, it’s the opposite. So if you have the means and the time, take revenge on those awful, pre-6th-grade trips to the “Husky” section at Sears (I was there too my fellas), and get something that looks great, feels good, and most importantly, fits.

Notebooks —> Notebooks

Dirt cheap or spendy. Tiny or enormous. Whatever your preference, now’s not a bad time to see if you need a new stack of stuff to scribble in. And if you’re rolling your eyes at using good ol’ pen and paper in the digital age? Don’t knock it till you’ve tried it. Using a notebook and pen or pencil is a lot like wearing a wristwatch. The benefits over your smartphone are numerous.

Pens/Pencils —> A nice pen

While we’re in the pen and paper aisle, let’s find something better than a bic that your co-worker Pete has chewed into a shiv. No, you don’t have to get insane and go for something in the hundreds or thousands (pens can get stupid expensive) of dollars. Just something that feels good in the hand, and is a pleasure to write with.

Boots/Galoshes —> Dress or Heritage Work Boots

Used to hate having to put on boots for the walk to school. HATED it. Now I can’t wait for boot season. So many types of boots worth owning… so little time to wear them.

Art Supplies —> Art for your home or office

Do they even teach art anymore? I really, really hope they do. Even though I stunk at it. Whether it’s an original by a friend or a local artist, or a picture you took that you’ve always wanted to have printed on canvas, or a classic off Art.com or somewhere like that, treating yourself to something new on the wall is rarely a bad idea. Pictured above: Lake Michigan by Ben Madeska. I bought it. And you can’t have it.

Calculator —> Wristwatch with a Slide Rule!

Wow we’re stretching it here. Plus, I seriously doubt two things: First, that calculators are still required back-to-school buying equipment. Remember those bulky graphing calculators from the 90s? Pretty sure those are obsolete now (the device, not the math). Second, I also highly doubt that anyone with a slide rule on their watch actually uses it. But if you do? Good for you!

Loose Leaf —> Stationery

A little different than notebooks. Why? Because Loose Leaf was usually something you’d write on, but eventually hand over to someone else. Same goes for stationery.

Lunchbox —> Tote or Dopp Kit

A smaller thing to put smaller things in that otherwise wouldn’t have fit in, or, needed to be contained within the bigger thing that you put bigger things in. I’m convinced that lunch boxes are one of the first status symbols that we’re introduced to as humans. You think your Hot Wheels lunchbox is cool? I mean, it’s timeless and all, but check out that kid over there who has the BRAND NEW Return of the Jedi number, COMPLETE with the Ewok thermos. Man. Now THAT was a lunch box. I had that exact Return of the Jedi lunchbox. I loved it. And then one day in kindergarten or first grade (I don’t recall) as I was emptying my crumbs and yogurt container out of my lunchbox at the end of the lunch period, the box slipped out of my hands and fell all the way to the bottom of the tallest trash can in the lunchroom. I was painfully shy as a child, and I froze. It was really far down there. I wasn’t sure if I could reach it. And I was terrified that someone would see me digging in the trash. No matter that my cherished Ewoks lunchbox was at the bottom of that black plastic pit. And I just couldn’t bring myself to tell a teacher because I felt absurdly foolish for letting one of my most prized possessions literally slip through my fingers. So I walked home later, crying all the way, and my parents were irritated because not only had I literally thrown my lunch box away, but also because I couldn’t get up the guts to ask a teacher for help. (“But why didn’t you just ASK?!?”) So for the rest of the year I had to use a lame, bright blue reusable lunch bag (something like this) that my Mom had been carrying with her to work. And it was a daily, fluorescent reminder of what I once had, but was now gone.

And THAT… is why therapists make so much money.

Good luck to all of the parents out there with kids who have to do REAL back to school shopping. Also, if you’re still in school? Good luck with the rising costs of tuition and books and all that stuff.