weatpants are among the least-worn pieces in my wardrobe. I reserve them for rainy days indoors or my weekly Pilates class, but they're rarely something I reach for when getting dressed to leave the house. I have nothing against a full sweatsuit in public. It's just not my personal style.

I recently heard designer Michael Kors say that the worst compliment he could receive about his clothes is that they “looked comfortable.” While I wouldn't go quite that far (what's wrong with a little comfort?), I do think there's something to be said for not surrendering entirely to sweats.

So I decided to experiment. By playing with proportions, unexpected layers, and contrasting footwear, I set out to see whether I could make my classic black Gap sweatpants feel like something I'd actually want to wear beyond the couch. Think tailored blazers , interesting flats , and a few styling tricks borrowed from the rest of my wardrobe.

The results surprised me.…