This Is a Sweatpants-Free Zone: Dressing Casual, Not Sloppy

I’m embarrassed to admit it, but … I’ve worn pajamas in public. (Lowers head in shame.) I don’t know why I thought my old ratty PJs were cool enough to venture beyond my couch, but looking back I realize there’s nothing worse than aiming for casual cool, but hitting the sloppy mark instead.

Other sloppy atrocities? The time I wore messily-ripped cut-offs, a stretched out, oversized gray T-shirt, and ratty flip-flops to my brother’s law school graduation. The outfit might have been good for the beach, but not so great off the sand. And I can’t forget my Mary-Kate Olsen phase, where I tried to copy her hobo-inspired looks but looked more like I was attempting to hide shoplifting efforts under my dress. (Grimace.)

Click here to find out how to dress casual cool but not sloppy.

Here’s the issue: I want to dress comfy and have that “I just threw this together and look amazing” vibe. But to actually achieve that casual cool look, I’ve learned that you can’t just literally throw everything together and expect it to gel. You need to take into account a bunch of things, like proportion, fit, accessories, fabric choice, even what type of shoes you wear.

I know that’s a lot to consider when you just want a casual look but trust me, these tips will keep you away from sloppy fashion mistakes. (MK, are you taking notes?) But to begin, here’s one very basic casual cool rule: Never wear pajamas out in public — EVER.