• Oversized Grey Cardigan: Michael Michael Kors, via Nordstrom
• Olive Green Tee-shirt: Banana Republic
• Black Leggings: Nordstrom
• Brown Riding Boots: Franco Sarto, via Zappos
• Lucky Socks: gift from FIL

There are days when I crave structure, whether it’s from a well-managed class, a good workout or a crisp blazer. And then there are days when I don’t. Days when I can’t imagine wearing anything with a zipper, when I want nothing more than to curl up under a blanket with a stack of papers to read and intermittently work and snooze in front of our sunny window. While I have my share of lazy work days, I tend not to indulge these sartorial desires for flexibility and looseness. But in honor of broken rules, expanded comfort zones and downright body image boldness, I decided to try taking that one last step into the unknown of the skinny bottom half: leggings as pants.

As the other emily and I have discussed, leggings-as-pants long held a spot on our list of “trends we swore we’d never wear,” I have to say there were things I loved about this outfit. On a day when I was feeling admittedly terrible, the soft, relaxed shapes made me feel comforted and nurtured, while the boots reminded me that I wasn’t in fact wearing pyjamas. The relatively fitted tee made me feel like I still had some shape under the oversized sweater, while the sweater provided ample coverage and kept me from feeling like my, ahem, ladyparts were on display for all to see. I should note, for context, that I didn’t wear this look at school, work or in any borderline formal occasion.

I won’t wax rhapsodic and claim that wearing flimsy leggings on my bottom half made me appreciate the strength of my legs and slayed all my body image demons, but I will say that this outfit was less of a catastrophic body image fail than I expected it to be. The combination of comfortable and on-trend shapes made me feel confident in what I was wearing, though, and gave me the freedom to think about other things on a day that I needed to plug on through. And maybe that’s a particular, and intriguing, kind of body image win: the kinds of clothes that make you feel neutral if not unambiguously positive, that free you up from thinking about your body or how you look in them. It isn’t the world’s most triumphal of feelings, but in a week that’s been full of both body ills and body-image weird, I’ll take it as a step in the right direction.

How do you feel about leggings as pants? How do you feel about experimenting with new trends that challenge your conceptions of what you “should” wear? What rules did you break this week?