When I was at H.B. Plant High School, the adhere-or-die dress code standard for males was: khaki bermuda shorts, a polo shirt (emphasis on edgy colors like pink and lavender), and Rainbow-brand leather flip flops or, for a period, Birkenstocks. Few boys ventured into the likes of any apparel that could be construed as goth, feminine, or androgynous. Being a young gay, the last thing I wanted was to stand out.
I did make minor adjustments to the uniform though – wearing Burberry polos instead of Lacoste or Ralph Lauren, and black Birkenstock clogs rather than brown. On a spring break trip to Seattle, I discovered what would come to define a genre of my personal style: a pair of simple leather Prada driving shoes (loafers with multiple individual rubber pads on the bottom for better pedal traction while driving). They were on sale at Barney’s, and were the most I’d ever spent on a pair of shoes.
From that point forward, though I stuck with the shorts and polos for years after, I traded flip flops for my loafers. Everything about them was wonderful. They had a heavenly leather scent that only the Italians can seem to get right. They looked great on my feet (big fan of bare legs and no socks). Wearing them meant I was stylish and refined.
For the first time, I realized that the best everyday pieces are simple. Some things are better with embellishment and detail, but many others come down to the right material with the right texture, the right lines…and they just work, consistently. I fell in love with these shoes, because they were an everyday art form.
Eventually, several years on, I wore a hole in the toe of them. Driving loafers are great shoes, but by nature they’re soft, so they don’t have the same sturdiness as in a hard-leather shoe. Since then I’ve dabbled in many other brands – Zara, Cole Haan, John Varvatos – none of which have pleased me so as that first pair did. I bought a black patent pair of driving loafers in Paris from Tod’s, and because I wear them only occasionally, those have held up quite well and remain a dressy go-to.
When I started wearing drivers, no one else was, at least at my age, in Florida. Since then, they’ve gone mainstream, and you can find many driver choices at brands likeÂ Aldo, 1901 (the Nordstrom house brand), and Hugo Boss. For a casual alternative to sandals, or sneakers, those are all great choices. If you have additional resources, might I suggest the following:
Gucci Auger black diamante-detail loafer – $430 – not for the attention-seekers, just high quality and classic
Prada double-sole loafer – $580 – these remind me of a stylish older gay man with a cheeky dressing attitude
Billy Reid faded blue canvas driving shoe – $140 (sale!) – at first not completely convincing, but I like them, and they’re a steal
Tod’s yellow textured leather mocassins – $450 – love little details like the scoring on the leather, and yellow is bright!
Mr. Hare bright red leather drivers – $415 – more bold color – and with contrasting white rubber sole
Pair any set of drivers with jeans, shorts, or chinos for a ‘thoughtful but not too concerned’ look. Bright colors are playful and fully appropriate.
With the weather turning toward chilly, drivers aren’t a logical choice. But, off-season means more sale opportunities, and in Florida, an 80 degree Christmas is not unheard of. Elsewhere, preemptively stock up for good spring weather.
No other shoe style can say the same thing that a good driver can.Â Boat shoes are similar, but have a nautical (and now hipster) element that gets stale. Tom’s style slip-ons are comfortable and cheap, but rarely boost the style quotient. If you are in the market, I suggest a starter pair of drivers.Â After all, anything invented by the Italians must be an instant classic. And you might just fall in love.