Quick background: at one time I owned over fifty pairs of sneakers, including all 21 of the original Jordans. All authentic of course, and now all sold on eBay, mostly in exchange for designer clothing.
Being a basketball player for most of my life, I think I’ll always have a soft spot for a pair of original J’s. I’ve been wearing them for so many years, why stop now?
These (or the III’s featured previously here) are my favorite Jordans. MJ’s first sneaker with Nike, 1985. The shoes that were officially banned by the NBA because they broke the “uniform policy” and the black and red colorway was considered too “aggressive”. (MJ of course still wore these in every game of the ’85/’86 season. Nike gladly paid the $5,000 per-game fine)
Here’s another move from back in my bball days: color matching.
Remember the days when you were the man if you had the latest Jordan colorway, with the perfectly-matching-no-matter-how-obscure-the-color t-shirt? Well I guess I haven’t completely given up on them. I still think it’s cool to highlight color accents in an outfit once in a while. Just remember to do it rarely, subtly and in good taste.
Again, would I recommend this look to every guy? No. But do I feel that this authentically represents part of my personality/individuality? Yes. As I’ve written before: I don’t necessarily encourage copying my personal outfits, but rather understanding the concepts that helped generate them in order to create a style that is your own.
Sneakers by Air Jordan (original colorway, re-released in 2009). Chinos by Ralph Lauren Polo (34×32). White oxford shirt by Band of Outsiders (size 3). Black cotton jacket by Gucci (size 50). Watch by Montblanc (42mm Timewalker). Watchband off eBay. “Clubmaster” shades by Ray-Ban.
Wearing sneakers with a tailored pant and slim shirt can be tricky. It’s important to choose a sneaker that is not too bulky – even though these Jordans are high-tops, they have a relatively streamlined silhouette (not much padding in those 1985 bball sneaks). I also bought them a half size smaller, to accomodate for their slight bulkiness (as I do with most sneakers).
Also, it’s important that you pair the sneakers with a pant that has a narrower leg opening and an inseam of decent length – a little “puddling” down the leg helps introduce the shoe and keeps the feel of the outfit more laid-back and casual. Here I’m wearing a pair of chinos with a 16″ opening and a full break (even after one roll), for example.
Remember to keep the rest of the look muted with neutral colors (let the shoes make the statement), and keep it casual with an untucked, open oxford and a lightweight layer.
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