Middle school was a bad time to prove one’s cool. Drawers of Top Dawg T-shirts. Depp No. 5 to replicate Vegeta’s ‘do. And bikes. The most devil-may-care rolled into the parking lot, coveted logos flashing in chrome frame: GT, Diamondback, Haro. I wanted that flash.

My dad — a man who values bargains so much that he tried convincing a merchant that he, too, was Korean — pleaded with me that my five-year old Huffy was just as good if we painted it navy and slap some stickers on it. Turns out, the paint couldn’t unwear the rust from years of learning, and I had outgrown the bike anyway. The bike we painted and polished never saw a foot of that parking lot. I remained uncool through eighth grade.

Value has been one of the challenging skills in establishing a permanent style. Whether it’s a wristwatch or trousers, I want something I’ll want to wear now through old age. I want to care for it, let it share its age gracefully, and carry on a story, of which my wear added a chapter. But I’ve found it’s such a minefield out there. Can I really justify dropping five thousand dollars on a handmade Neapolitan suit? I can make a case to my wife, but unless my teaching salary tripled, I’d have a better shot re-piercing my lip.

Sometimes I regret that I’ve fallen for the world of suits. I can’t un-see the cheap sheen of synthetic cloth in department stores. I seek the priceless imperfections of hand-sewn details here and there. Well, realistically, there’s always a price, for the beautiful land of menswear is unfortunately a land of luxury. The best I can do is use practicality as a compass. Save up for a $1400 off-the-rack three-piece once a year, perhaps. Then there’s always another trick: suck it up and go for “good enough.”

I’ve had my successes digging for bargain-bin substitutes of classic menswear. My navy Uniqlo blazer, though 60% polyester with modern-width lapels, fits my shoulders excellently. This is a rarity, however. When we buy cheap, we get cheap. My black oxfords prove this much.

At this point in my study of worthwhile investments, I’m aware that when you buy a pair of leather shoes, you’re paying for the quality of the leather, as well as the quality of construction. Neither of these were priority in my Florsheim captoes. Four years ago I found them at Nordstrom Rack for about sixty dollars; it was finally time to stop borrowing my from dad’s collection of clearance Rockport slip-ons. They’re still my only pair of black shoes, so they’ve survived the move to China. Being a devout sentimentalist, I’ve refused to replace them until they’re beyond repair.

Recently, I finally figured out the art of the cap toe shine, which I was able to achieve on my Grenson monk straps. On a whim, I tried to see what I could manage on the Florsheims. With a tin of black wax and an old T-shirt tourniquet-wrapped around my hand, I repeated the process of dabbing wax, water, and elbow grease. Ten minutes in I noticed the toe didn’t get to a shine nearly as quickly as the Grensons. By the time I finished, It took well over twice as long. My forefingers rubbed the air in tiny circles.

But hey, I was able to do it. There was a near patent leather shine to the toes. “You done made ‘em brand new again!” I thought. And then I wore them the next day.

There I was, grading papers in class, and I saw my shoes sweating. I rubbed the condensation off, when my thumb turned black. The layers of polish were flaking off the cheap leather and onto the ground. It was my Huffy all over again. Two hours of work and the feeling that I beat the system crumbled in a coal dandruff.

So I guess value is important. This wasn’t a lesson as much as a reminder. What I did learn is that like anything important, value is personal. If you’re happy smoking fine Caribbean cigars in JC Penny suits, great.  Don’t let me or anyone else tell you otherwise.  For me, I’ll be on the hunt for a new pair of black shoes, and this time around, I’ll be ticking boxes for quality all-around.

I want a leather that doesn’t require a Netflix marathon to shine. I want soles that I can replace in ten years, then ten years more. I would love 100% percent bespoke, but I’d never want to wear them outside of the house. I’ll let time warp a fine shape out of them instead. All this is good enough for me.

The Line-Up