Can I mix a sleek blazer and dark jeans with a fun T-shirt and sneakers for a dinner date at a casual to-mid-range restaurant?
There are sneakers and there are sneakers. There are sneakers that cost as much as a suit. There are worn-out canvas Converse. A soft-soled shoe with some kind of interesting colour scheme – maybe some suede bits – and a bright clean lace that stands out, possibly in a contrasting colour, is the mark of a stylish guy. The outfit you're describing is fine for casual dining, if you want to give the impression of being an artsy, maybe even bohemian guy. You're certainly not promising your date a future life of caviar and beachfront property, but you're showing her that you may enjoy the odd graphic novel and indie band.
That's great – but it gets more difficult to pull off with age. The farther you outdistance 40, the harder it is to confidently inhabit casual clothes. They just tend to look slack on an older frame. Your "sleek blazer and fun T-shirt" will be less impressive if they are stretched over an embonpoint. Your funky shoes may seem merely comfortable if your posture is stooped.
Also, if you're over 40, don't overdo the hipster accoutrements. If you were to add a hoodie to the outfit above, I would say you were pushing the look into I-still-livewith– my-parents territory.
That said, I have seen art dealers in their 60s showing up to openings in fine grey suits and bright red running shoes that match their plastic spectacles and set off their white hair and no one would have thought them poor or trying-too-hard. The key with such daring is to wear one dressy item, like a suit or blazer, for every piece of streetwear.
If you keep the quality of all clothes high and make sure they fit, you won't look like an aging grad student.
Russell Smith is a novelist. His recent memoir, Blindsided, is available as a Kobo e-book. Have a fashion question? E-mail email@example.com.