My Para sweatshirt is already in regular rotation—it goes with literally everything. I usually wear it with slimmer pants or French tuck it into some mom jeans. Next time I go to grab it, though, I’m going to slip into the wide-legged, jardigan-knit Rogala pants. The pairing of two oversized pieces, balanced out with the slim Lana boot, is an unexpected twist on a weekday staple and would definitely motivate me to take a much needed walk around the block.

What’s the first thing you’re going to do when we’re allowed to be around other people again? I’m going to get dressed up in some kind of over-the-top look, go sit at a fancy hotel bar, order a cocktail and appetizers, and people watch for an entire afternoon. I figure it’s never too early to test-drive some outfits for this big moment, so recently, I’ve been enjoying some classy happy hours at home with a very hotel soundtrack, a curve-hugging jardigan knit skirt like the Harlem, M.M.’s version of my favorite jean jacket (ours is linen), and those fail-safe Lana boots. I might not be able to do very much people-watching from my couch, but the drinks are much cheaper.

For some reason, this look reminds me of Meg Ryan in You’ve Got Mail. Sure, her character wasn’t exactly the definition of “cool,” but she definitely had personal style, passion, and some really great sweater sets. (Plus, in 2020, everything ‘90s is new again.) So when I need to feel both bookish and on trend, I hop into my Tinsley trousers, throw on my favorite Leslie T-shirt, and cinch my Woolf jardigan around my waist. Then I sit down to write emails all day, just like she did. All that’s missing is that satisfying “whoosh” sound when I hit send.

My least favorite thing about dressing for winter is a winter coat. Spending so much money on something I hate wearing feels like a slap in the face. Plus, as a petite person, I’m basically swallowed by the warmest options. Most Decembers, I find myself layering to the point of absurdity, just to avoid having to put on a giant parka. What I’ve found in my many years of this dance is that there’s a way to make layering look neat and put-together (as opposed to thrown on all at once). It’s all about proportions. You’ll want a slim underpinning, like the Axam, to start the whole thing off. Then, add another layer that’s still a bit fitted but has some more weight, like the Merritt. Finally, top the whole thing off with a boyfriend blazer that hits in all the right places. This look works especially well with fitted pants, like the sexy Curie.

My Sant Ambroeus used to sit on the back of my chair in our New York office, just waiting for the tad-too-chilly air conditioning or that first crisp walk to the subway in the fall. Alas—I control the thermostat in my home office (a positive!), and who knows when I’ll ride the subway again, so my reliable Sant Ambroeus needs a makeover. I’m thinking I’ll repurpose it with sneakers and a pair of tailored pants and wear it on days when I need an extra bit of motivation. Who knows—maybe I’ll even make a latte in a to-go mug and pace around my living room listening to a podcast, just like old times! Sort of.