Welcome our new Advice Guy column

I’m 28, broke and have a shit ton of student debt. Why didn’t I listen to my parents and become a doctor?
J. – 28, Los Angeles

If people still listened to their parents we’d all still be listening to Benny Goodman in poodle skirts. You didn’t listen to your parents for the same reason everybody else doesn’t listen to their parents: because they don’t want to be them, because you want to do your own thing. And doing your own thing means a certain amount of failure. You know what happens when you fail as a doctor? People die, amigo.

My girlfriend says my white socks look stupid with my outfits. Why can’t I wear white socks?
W. – 19, New Orleans

White socks on a man over 18 say to the world “Hey, look at me, I never got over high school and don’t care about the details.” White socks will work if you’re wearing boots and lugging things around all day – hey, any way to make a living, right? – but if you’re trying to look good for a client or a gal, at least have the dignity to move on from the white tube-sock era. Please. Think about the rest of us.

What does one wear when traveling?
B. – 29, Washington DC

Traveling used to be a sexy event. Now, people wear sweatpants and other sartorial white-flags. I suggest dressing for comfort – after all, you’re going to be in a metal tube for several hours – but don’t be afraid to make an effort. Brands like Uniqlo and J. Crew straddle the line between comfort and style easily. And with the glacial pace of men’s fashion, there’s nothing wrong with dressing down a blazer with a plaid dress shirt or dressing up your most comfortable pants with a great sweater. Like most things in life, it’s all about balance. If you make even 10% more of an effort than the people around you on the plane or the train or the automobile, you’ll be sure to look just that much better than them. Give it a try.

Tags: advice guy