Featured: Why I Dress Carefully

Why I Dress Carefully

By Jonathan WC Mills
October 28, 2013
32 comments

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.”

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32 Comments on "Why I Dress Carefully"

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Thordur

I don´t get what is all the fuzz about this article.

This article is all about being the best version of yourself, driving or not.

Nghia Nguyen
Nghia Nguyen

I’d like people to see the Grin I’m wearing as driving. 😀

John Cochran
John Cochran

Great article. Once again, love this website.

Jeff S
Jeff S

oh crap, I have completely missed it as I wear my beat up DU cap that is sweat stained and falling apart, tshirt and jeans on purpose when I am in my porsche – striving to be the jackwagon that I know I can be

FRanco Jo
FRanco Jo

Good article! I do like to dress with purpose, especially when driving my sports sedan. Dressing right really makes an impact on the whole passion experience (includes driving). I’m also aware that it all depends on the personality of each individual. Some people just don’t care about how they look to the outside world, and thats ok as long as they are happy.

Kyle Wilks
Kyle Wilks
Jack G. got it right…wear what you love, and forget about the rest. Sorry Jonathan, I don’t see the need to wait until retirement to dress comfortably via a simple T-shirt when driving (life is too damn short for those types of excuses). I get in my vintage cars to enjoy the driving experience…the way I do that is to forget about things like shirts, gloves, hats, pants, etc. About the only thing I will agree w/ is your thoughts on shoes & sunglasses…everything else is a fashion show debate I could care less to be a part of when… Read more »
flooglemop
flooglemop

I concur.

Afshin Behnia
Afshin Behnia

It definitely IS about wearing what you please and dressing comfortably. However, some people prefer and are more comfortable to dress stylishly, whatever that means to them.

Jonathanwcmills
Jonathanwcmills
Thanks for the all the comments on this article. For what it’s worth I did write it to be provocative, however it’s not a suggestion to wear a costume. I am simply asking the question; if you care about what you drive, should you also care about what you wear? Perhaps this makes people uncomfortable. But it’s a fair question. For me, as I say in the article, it’s really about time and place. When I’m retired (like Jack Gilbert) I’ll wear jeans and a t-shirt and smoke a cigar and drive the heck out of my (illegal) gasoline powered… Read more »
Jack Gilbert
Jack Gilbert

Guys, I am going to assume this is some kind of spoof article you are putting on the site to pull some people’s chains. If it is not a spoof then shame on you. I dress comfortably to drive my old cars. I don’t give a damn what others think about how I dress. I wore a suit and all the other trapping of success for 42 years and today I wear what I damn well please!

Kuroneko
Kuroneko

It’s a fine line between dressing stylishly, and coming off looking like a prat. If you have to think about it, or try too hard, you’re def over the prat line. Kind of like the need to add embellishments to otherwise simple things – wearing name branded clothes when driving the same branded car, calling electric ‘electronic’, simple stories about cars have to be ‘back stories’, and adding extra initials to your name. Over the line, trying too hard… Neko.

Matthew Lange
Matthew Lange

In my younger days, I was very much a fashionista but not so much these days although my Wife does call me a label whore 🙂 When out in the Daytona on a hot day I prefer lightweight linen clothes to counter the combination of heat soak, weedy AC and leather seats. Good driving shoes are a must though, Car shoe, Tods or Pirelli being my preferred choice.

Peter McCormick
Peter McCormick

This reads like copy from a Peterman catalogue. Speaking of copy, “impact” is not a verb.

Jorge Irizarry
Jorge Irizarry

You forgot the watch….

Art Harvey
Art Harvey
Interesting. I will absolutely try the period shirt-and-tie approach – just to see how it makes me feel. Some owners seek to project a persona or “style” that amplifies their classic car ownership, some couldn’t care less, while others don’t want to come off as a poseur. Admittedly, yes, my attitude towards a day of driving is influenced by what I select to wear, and I’m “aware” what my choice of style projects – so I do select my “kit”. Each drive and car carries its own set of factors. Whether it’s taking the wife for a leisurely cruise of… Read more »
Anders Holmberg
Anders Holmberg

One of the best bit of reading I’ve had for a while, very well written!

Drive Tastefully

ZeGerman
ZeGerman

The tricky part of attempting to dress as though you’re in an earlier design period, as this article does not state outright, but is certainly alluding to, is to not come off as contrived. It has to be genuine and authentic. The “dapper” trend that we are beginning to see more of these days is fraught with peril if not executed properly, and probably less than 10\% of people are capable of pulling it off.

Todd Cox
Todd Cox

I always do my best to fit the part. Thank goodness for MadMen. It is eternally nodding back to 1964 when I settle into my car. I revel in it. When men were men and made no apologies to a necktie, a fitted suit, or a well tuned set of tailpipes.

Justin
Justin

Are you a hairdresser from the 1950s?

Inigo Loy Colmenar
Inigo Loy Colmenar
The people who drive in style are the same checkbook mechanics that dont know how to work on cars. Jay Leno wears the same denim shirt and pants all the time and he does not care what he wears. I am pretty sure the stylish Georgio Armani does not know a 1/4″ from a 3/8″ drive ratchet either. When I am driving a classic car, I know Im gonna have to pull over the side of the road and tinker with it and see how things are working and I want to make sure that I am dressed for the… Read more »
Paul Steel
Paul Steel

To flip that logic, people that know how to use a spanner don’t have style or care about there appearance 😉

Todd Cox
Todd Cox
You couldn’t be more wrong. I do all the wrenching on my 1996 Miata and my 1964 Sunbeam Alpine. As have with my ’58 Bugeye Sprite, my 1971 Karmann Ghia Convertible, and my ’57 Ragtop Beetle (amongst a sea of other less notable machines). The apparel one wears to reflect the car is yet another avenue for driver and car to connect. A true mechanic; a true *craftsman* knows this. It is the difference between taking possession of a car, and taking stewardship of it. There’s no bond in the former, and a deep connection in the latter.
John Cochran
John Cochran

Well said sir. We’re on the same page.

Josh Clason
Josh Clason

I have seen a few drivers with style on the side of the road tinkering on cars. In those cases they have had leather aprons they keep in the car for inevitable tinkering on the car that comes with owning vintage.

This isn’t for everyone and that is ok. People get satisfaction from vintage cars in many different ways and this is one of them.

Inigo Loy Colmenar
Inigo Loy Colmenar

Ooh yeah. Just like those weekend Harley riders that don leather jackets, leather pants and bandanas. I guess you have to look the part, huh.

Leo Basile
Leo Basile

I have a 1966 Morgan that I have never driven with out either string back gloves or period leather driving gloves. On the cool days its either a tweed jacket or a proper wool sweater. On the cold days its my leather flight jacket, with said sweater.

Leo

Shervin Nakhjavani
Shervin Nakhjavani
Fully agreed. Fashion goes hand-in-hand with automobiles for me. Ever notice how the level of cleanliness between you and your car are almost always mutually exclusive? It’s either that you wash, polish, and detail your car to the tee and end up looking a wreck… or take a nice shower, groom yourself, and drive a dirty car. This is why it is imperative to perform the former first, and take the time to follow up with the latter. Every girl’s crazy for a sharp-dressed man, but the appeal multiplies tenfold when he’s in a sharp-looking car (and the same goes… Read more »
Lee Putman
Lee Putman

What kind of driving gloves are those? What car are you driving??? LOVE this article!

Josh Clason
Josh Clason

Not sure on the gloves but you should check out the ones from Autodromo. They are fantastic. http://www.autodromo.com/products/stringback-driving-gloves

Eddie Relvas
Eddie Relvas

Don’t know about the gloves, but the car is unmistakably a Fiat 2300 S Coupe.

Paul Steel
Paul Steel
Correct footwear is very important, currently I step out in a pair of smart doc Martin’s shoes, but I can’t drive my Triumph comfortably in a pair of DM’s, so I tend to wear trainers to drive and take a pair of shoes for the on-foot part of the day. I don’t purposely set out to match my cars era in my dress sense, but I happen to like the fashion of the mid-late 60’s, that includes the cars, music and clothing, and I feel good when it all comes together. My daily driver is a 2001 Jag XKR, I… Read more »
Daniel Kelly
Daniel Kelly

Dappered (referenced in the footnotes) just so happen to be one of my favorite daily reads. It’s nice to see these two worlds combined.

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