Why I Dress Carefully

I used to live with an Australian fashion model who later went on to start a successful clothing company selling ladies underwear. I’ll admit these facts put this woman near the top of a short list of good friends. And coming from the land of Vegemite and kangaroos meant her attitude and language was as colorful as her outfits, so she wasn’t shy about expressing her opinion—especially when it came to what I might be wearing.

“Good kit,” she would tell me. This was how I knew if I was ready to leave the house. Did I have the stamp of approval from my model roommate? If so, lookout, world. Knowing I was wearing “good kit” gave me the confidence to approach the day with a nudge and a wink. Having good kit meant that I was one step ahead of the guy who didn’t bother. It meant getting the nod from the boss or the smile from the girl.

In short, it mattered.

From shoes to chapeau, what you wear impacts your life, and when you drive it matters even more. I treat my car as an extension of myself. If I didn’t, I would drive a Toyota Tercel, a reliable little blob with no personality—but I don’t. My car is loud and maybe a little obnoxious, which means that what I wear needs to be a counterpoint. And yes, I think about this. When I dress for the day, I have a notion of my time, my place, and the journey ahead.

Lets examine the essentials.

Shoes. Your shoes are the interface with the pedals and in many cases, to women as well. (This is a fact by the way.*) First and foremost, your shoes need to give you the dexterity required to manipulate three pedals comfortably. You don’t need to be Ayrton Senna driving an NSX, but you do need to be able to drive. I was once forced to drive an MG in the dead of winter in a pair of size 14 Sorels, nightmare. Driving shoes are not just lovely pair of leather TODs. They could be a pair of trainers, dress shoes, or even a pair of lived-in cowboy boots, but you should make absolutely sure they fit both your feet, your pedal box, and your outfit.

Pants? Wear them. Not too tight.

Shirts. Now, I’m going to go out on a limb. I’ve always been told to dress for the job I want, not the one I have. During the week and evenings, I wear a button-up shirt and, on occasion, a necktie. In California this borders on sacrilegious, but I didn’t grow up in Venice Beach with my finger raised to “the man.” I grew up with Southern respect, and to me, respect is a piece of colorful silk knotted in a double Windsor. Plus, wearing a tie automatically adds value to your car (maybe even a good ten percent). I believe it’s worth dressing like you know how to drive your car, your desk…your life. On weekends a black t-shirt is appropriate.

Hats. Tough call. In general, I’m opposed unless you’re motoring, “top down” which I don’t do. Living in the sun belt, I see a lot of convertible owners wearing what was clearly the hat sitting at the bottom of a dirty beach bag. This hat is usually a last-minute grab to keep from burning their heads. My response? Lose the hat or purchase a more sensible car—one with a roof, for example.

Gloves? If you have a wooden steering wheel or it’s below freezing. Go for it.  

Finally, we reach the most important piece of driving kit: sunglasses. Sunglasses are the one piece of equipment that provides both fashion and function. There are many choices when it comes to sunglasses; so many, in fact, that it would be silly to attempt to cover them all. However, a person’s frames say a lot about the wearer, so act accordingly. If this confuses you, ask your wife or girlfriend for clarification—if you’re single aviators are a reliable choice.

Having good kit isn’t difficult. You don’t have to be uncomfortable, you don’t have to spend thousands of dollars. But it should make you should feel confident. Drive your car with passion, then step out of it to face the world with confidence.

Have good kit and Drive Tastefully.

*Ask A Woman, dappered.com ”…yes, women notice shoes. And we judge. We judge your shoes.”