1/6DAY ONE
“I’m not very ladylike and I don’t feel comfortable being too polished. When I’m wearing a silk dress like this one, I always like mixing it with a bit of denim, or a chunky pair of shoes, or a sneaker. Otherwise, I feel too delicate and like I need to behave that way!” High-neck flare dress, $568, dvf.com
2/6DAY TWO
“I have a design background, so things that are glossy or colorful usually catch my eye. I’m wearing this dress with sneakers, but you could also wear it with sandals in the summer, or with heels for a wedding or night out.” Sleeveless scarf dress, $428, dvf.com
3/6DAY THREE
“I always wear long dresses for flights so that I feel like I’m inside a bed. It’s so much more comfortable than wearing pants! And I rarely wear jewelry when I travel, though I like having a smaller bag to keep the things I need to access quickly, like my passport and phone.” Color-block knit dress, $398, for information: dvf.com
4/6“I love this dress because it’s cute and colorful and I can still look chic and ready for a meeting right when I get off a plane, if I need to. It won’t wrinkle! I just wear a ponytail and a sweater, always, and I’m set.” Color-block knit dress, $398, for information: dvf.com; V-neck knit pullover, $298, dvf.com; Saddle shoulder handbag, $498, dvf.com
5/6DAY FOUR
“I wear a lot of heavy gold jewelry and this dress is great with all of the larger, statement pieces that I put on even during the day. It’s like a big, fresh, blank slate. And I love that it looks like two pieces, but it’s just one.” Short-sleeved collared shirtdress, $348, for information: dvf.com; Hammered gold and stone choker, $298, dvf.com; Studded circle wristlet, $248, dvf.com
