I can’t help but laugh when I hear guys tell me they’d like to dress like I do, but it looks way too uncomfortable. My suits are just as comfortable as the sweats I sleep in.

Take this flannel suit as a perfect example. With no shoulders and hardly any structure in the jacket, it feels about like I’m wearing a sweatshirt. The pants are better than any jeans I’ve ever owned either.

What most men are really complaining about though is not the physical comfort of a particular piece of clothing or ensemble, but the social comfort that comes with presenting yourself as indifferent to your appearance.

If you don’t look like you care, no one will accuse you of caring.

And that’s about as easy and comfortable as a guy’s existence can get. Too bad there’s absolutely nothing masculine about a life dominated by indifference.

If you want to look like you care but don’t know where to start, check out my Staples – 30 items that work in any man’s wardrobe and help communicate a willingness to move beyond indifference.