The whole experience of flying (checking in, freaking out because your passport has gone missing, waiting in line at customs) can be a pain in the neck. Which is probably why, when we dropped by Billy Bishop Airport, we saw many people who seemed to have decided that they’d be better off wearing whatever was most comfortable in their closet: sweatpants and a loose T-shirt, or a wrinkled summer dress. Our grandparents often told us that it’s important to dress nicely for the airport, if for no other reason than airline staff are more likely to offer unexpected upgrades and good service to well-dressed people (we’re not saying this is right, but we’ve seen it happen). So, we went in search of the well-attired city traveler, and we’re pleased to admit that it was far from slim pickings, with at least 20 of Toronto’s travellers following grandma and grandpa’s wisdom.
Without a doubt, members of older generations were travelling in the most classic style: a braided belt on a tourist from Kentucky for example, or a well-positioned panama hat paired with a nicely-fitted suit. And it isn’t just the outfit that gets consideration—we saw plenty of nicely combed or brushed hair, and a snow white beard with nary an in-flight sandwich crumb in sight. Young travelers were no less stylish, with an ad executive from Chicago showing up for a Toronto meeting in a lovely above-the-knee little black dress, and a young tourist wearing the coolest checkered Dickies backpack. We can’t confirm that any of these outfits actually won these travelers better seats—but they certainly helped us realize that there are still people who take the time to dress up for special occasions.