I've been riding bicycles for transportation nearly continuously for around forty-five years. For about the first twenty years, I rode mostly in blue jeans and tennis shoes. Blue jeans are tolerable for short rides of two or three miles, sometimes—if it's not too cold, not too hot, and not too wet. (Cold, wet blue jeans are truly a misery, even if you're not trying to pedal in them at the time.)
But after a while I started riding farther and farther. Southern California is a big place, full of vast extravagant beauties and small hidden charms, and the jeans weren't up to snuff. Or maybe I wasn't masochistic enough to tolerate them. Reluctantly, I bought some (plain, black) Lycra tights.
Epiphany! I felt as though I could ride twenty miles farther with almost no effort! (And don't tell me I needed to trade in my road bike for a bolt upright Dutch cruiser—not till you've ridden one back and forth over the Santa Monica Mountains for a few hundred hot summer miles. If you survive that, I'll consider what you have to say.) I went farther, though not faster, up more and steeper hills, explored smaller and more obscure roads, discovered worlds both human and natural I'd never suspected. I won't complain about my time in Lycra.
I was never shy about wearing tights, either. I've got nice-looking legs, after all that riding, and Californians are not generally uncomfortable with being human anyway; the body is not evil here. But still, we have all kinds, and I knew some other people were in fact shy about men in tights, and I was tired of carrying a change of clothes with me to work, and...well...I missed having pockets!
Waist packs struck me as somewhat awkward, and one more thing to carry around. So I designed and started manufacturing the dressy bike duds sold on this website. Trying to split the difference, making elegant clothes that still work well for longer rides. (Anything suffices for a one-mile ride, but that's a walk in my book.)
It worked. In fact, though I started off wearing Lycra tights under my wool knickers for longer rides, after a while I gave it up. Rode my most recent century—on a vintage Italian racer converted to fixed gear—wearing regular off-the-shelf boxer shorts under my Classic Wools. No problem!
But, though I move along fairly quickly, even now while recovering from a small stroke, I don't go roadie fast. If I did, I would be in Lycra. More work, more wind, all that stuff.
Of course, I've heard some folks say that there's no need to go fast on a bike. And they're right! There's also no need to drink good beer or fine wine, listen to music, sit at a sidewalk café with friends, or stop for a moment to look at the sunset. We do those things because they feel good. And so does riding a light road bike fast. Even if you're riding it to work! (Which happens a lot in Southern California, where work might be twenty miles away.) This makes Lycra much more practical than a suit, trenchcoat, and beret for that particular ride.
What makes clothing "practical" anyway? Anyone who remembers the Mao suit prevalent a few decades ago in China when it was still the "Kingdom of the Bicycle" might know the answer. As for the rest, any decorative clothing is as silly and pretentious as team kit, if you think about it. Especially the heels and minis, the sundresses, the suits that have become the modern cliché of velocipedal fashion. Somehow, a "practical" bike has been redefined as one that lets you wear impractical clothes.
Heels cause deformities; my own mother had to have her toes broken and reset after wearing high heeled shoes for most of her middle years. And suits! Cinching a vestigial scarf tightly around your neck to proclaim solidarity with the corporate culture that has brought life on Earth to the brink of collapse? This is chic?
Sure, there are Lycra louts out there. So what? There are louts everywhere, in every type of attire. Disdaining someone because they don't reinforce your preconception of what is hip is profoundly loutish in itself. Reminds me of Mick Jagger's line in "Satisfaction," where he sneers (ironically, of course), "He can't be a man 'cause he does not smoke/The same cigarettes as me."
He might have been talking about those folks who judge us by the cut of our clothes and the shape of our steel.
Ride what you want, wear what you like, be kind to the people around you.
The rest is pretention.