Menswear, as they say, is a game of inches. Things don't move all that fast. Especially when it comes to dressing up—a shirt and tie under a suit jacket. When you think about it, what separates the clothes you're wearing today from what your grandfather wore when he was your age isn't all that different. It all comes down to proportions and individual style. So the more individual your style, the better.

Which is why we recommend wearing something with a little history to it. Maybe it's a family heirloom—your grandad's signet ring or the leather bag your father or older brother used for years until you convinced him to give it to you. Every time you use or wear these items, you'll think of your family. There's a comfort in knowing that you've got something that was once special to someone who means a great deal to you. That perhaps, some piece of them is imbibed in this inanimate object and a little bit of what made them such good men is passed on to you whenever you wear it.

Of course, not every old item you wear has to have such a strong personal bond. It could simply be a favorite piece you've had for years and years. Or a particularly great vintage item you uncovered somewhere along the way—in that little store you wandered into on vacation or your neighborhood secondhand shop. Either way, the item's had a life and somehow, that makes it more impactful. Whenever I'm trying on a vintage piece, I often find myself daydreaming about what experiences it might've been through. Maybe that's why I can always remember where I picked up a vintage piece and the details of that day. They become wearable mementos. Talismans of sorts. And they're often uniquely one-of-a-kind, which adds a nice shot of intrigue to whatever you're wearing.

When Valet. celebrated its fifth anniversary, I treated myself to a watch to commemorate the achievement. A first time business owner, I wanted something that would honor such a milestone. So I sprung for a Rolex. But I didn't want some flashy new one. I had my heart set on one that wasn't even being produced at the time. I'd been eyeing the simple, subtle style of the Air-King model for years. I looked and looked and finally found the perfect one at a jewelry shop specializing in vintage watches. There's nothing inscribed on the back, but a label affixed to the original box reads "To Robert, in honor of 25 years of service." Someone made a joke about how Robert had to work for a quarter century to get this and I'd only put in five years. But I told them that the web has made everything move faster.

Funnily enough, my Air-King just happens to be from the same year I was born. It seems fitting. After all, this is the kind of timepiece I'll have for the rest of my life and each year, it only gets more valuable. That's a good message to keep in the back of my head. And I've never worn anything in my life that has received more compliments.

- Cory Ohlendorf