Dawn Donohoo

How can I update my weekend look to look more pulled together but still cool and laid-back?

To add a little versatility, I would suggest adding a tie to your standard look. This will add an unexpected twist when paired with, say, a shirt and moccasins, but it will also keep you comfortable in what you already know you like. And you can also add a classic grey or navy blue cardigan in lieu of a sportcoat.

Can I wear black shoes with a brown suit? What are those rules?

There used to be a hard and fast rule that decreed “like with like” (there was another that said “black in the city, brown in the country”). But times have changed and the black and brown thing can definitely be done. That said, it can be done well and it can be done poorly—on the occasions when I’ve seen it look off, the guys seemed to have gotten dressed in the dark. If you want to wear black shoes with your brown suit, by all means go ahead—just make it completely clear that you’re doing it intentionally. That means keeping your color story tight (stick to brown, black and white—that’s it). And make sure that you absolutely stay away from colorful surprises like ties or pocket squares.

What shoes should every guy have in his wardrobe?

Leave the Imelda Marcos type of shoe wardrobe to your girlfriend—most guys can get away with the bare minimum (which means less decision-making in the morning). Without doubt, you should have a nice pair of black wing tips or oxfords—you can wear them to work with a jacket and tie or with jeans and a sweater on the weekends. I think a casual desert boot is a good thing to have for every day (my go-to is our suede MacAlister—it goes nicely with everything from jeans and cords to chinos), and I’d recommend a heavy, all-weather boot like a pair of Red Wings for winter and rain. Add a pair of classic tennis shoes (I happen to like Jack Purcells or Chuck Taylors) and you should be pretty much set for any occasion.

Tags: Dawn Donohoo, Fashion, fashion tips, Men