Not the Cool Kid

Today after work, I attempted to find comfortable walking shoes that are still nice enough to wear with darker jeans, khakis, or corduroys for fall. I have a weeklong business trip to San Francisco at the end of the month, and heels do me a great disservice on those ridiculous hills. Plus, it’s an all-company retreat, so the atmosphere is a little more, ah, rustic.

Anyway, this is apparently a Holy Grail of shoes – an elusive combination. At least it is when you’re just not cool enough to wear those trendy bowling shoe/sneaker hybrids. It is so depressing to walk into a shoe store, gravitate toward the ones that you had envisioned, and then find out that, no, you can’t really handle them, especially with all of these crazy colors and shininess. The price is a little startling, too; not that you’re cheap, of course, but one can only spend so much on shoes, especially if you’re not sure about them. Your eyes glaze over as you see periwinkle/chocolate brown and lime/gray combos, thick lug soles, athletic Mary Janes (isn’t that kind of an oxymoron?), and the stretchy non-laces that make up this strange genre of footwear.

Then, you manage to find a couple of pairs in the clearance section that are reasonably priced, especially with the buy-one-get-the-second-pair-half-off sale. So you grab some nylon sock things and try on a pair of relatively sensible brown ones. But you can’t figure out how they’ll feel with actual socks, and you forgot to bring some along, so how can you really judge them? You could try them out at home, but you never know about the return policy when it comes to clearance items, and it's anybody's guess when they’re on sale on top of it. You ponder the matter as you try on a black pair, and after a lap past several shin-high mirrors, the conclusion is clear. You are not this cool and you can’t pull it off. From the ankles up, you look like your normal self, and from the ankles down – whose feet are those? The shoes go back on the mismatch that is the clearance rack.

On the way toward the exit, you throw away the foot sox and gaze longingly at the purple and orange sneaker-type shoes (ooh, massaging gel insert), and the nagging question remains: “Isn’t there a happy medium between my cross-trainers and my pointy heels?” As you push through the door, you know the sad truth is that there is a happy medium, and it’s looking down on you and your pedestrian urge to buy a good pair of loafers.

... Or maybe that only happens to me.

Edited: August 16
Against my better judgment, I went back to the store and bought these shoes, a purchase driven by their sheer comfy-ness, and definitely not an increase in my coolness factor. After running them by JG, his sister, and my co-workers, the votes all seem to be in favor, so I'll keep them around. I'm not entirely sold on the shininess though...