A Jenna Lyons fun fact? She loves Rummikub, the parlor game that’s like a cross between Rummy (which you play with cards) and Mahjong (which you play with tiles, and a lot of tricky rules). But perhaps more importantly, she loves winning at Rummikub—and isn’t above playing dirty. Said Jenna with a laugh as she slid in between her reupholstered pink velvet couch and the coffee table: “I really like to play it when other people are drinking. Then you can really mess with them.” The blush tone upholstery worked doubletime as the ideal backdrop for Jenna's game look: “I felt like this frothy top deserved a gentle red lip and nude eye,” she explained. It’s a little romance, but balanced—plus, if you’re too shy to wear such a sheer top out, breaking it in at home is the perfect compromise.

While we helped set up the second “party” in the kitchen, Jenna played dress up in her bedroom. She started with a sparkly sequin top and white blazer, which felt… somehow not right. Next up was a slinky latex bodysuit, definitely outside of Jenna’s comfort zone. “I worked at a brand for a long time where we developed a look that was very iconic and clean,” she explained, “and being on my own affords me the opportunity to be more experimental, and try things I might not have before.” Ultimately, she landed on a look with a recipe like a mixed drink: one part chill to one part sexy (Jenna chalked up her abs to a recent obsession with the Tracy Anderson Method), and a dash of bold accessorizing. A warm smoky eye, pushed-back hair, and a nude lip maintained the balance between fun and elegant. And as tempting as it was to go straight for a margarita and call the shoot a wrap, we had one more look left.

Reader, even though bars, clubs, and—heck!—amusement parks may be open for business these days, the most fun spot in New York is probably Jenna Lyons’ shoe closet. It’s big, but there’s little space for minimalism: crystal-covered Tom Fords, strappy Gucci sandals, pointy pumps in every bright color and ironic finish (including one pair that bears a striking resemblance to Restoration Hardware’s yeti chair). “I have a tendency to appreciate opposites in a look,” said Jenna, and footwear is the perfect place to play with contrasts. “How many things can I mash up in one look? Give me a minute and I’ll keep trying!” she added with a laugh. Then she threw on a mens blazer with pearls, a smoky eye with a heavy pair of glasses, and dramatic false lashes with a heather gray sweatshirt. Ultralip in Lucite, which doesn’t add much but a sheer glossy finish, offered a palate-cleansing neutral to the chaos... er… everywhere else. Which happened to include a giant inflatable alien. Hey, if the past year has taught us anything, it’s that new friends are everywhere!