1. The Kiki crewneck sweater: A cozy and versatile piece with personality. (Also a favorite of the M.M. team.)
2. Sansa earrings: Big, bold silver hoops that make any look stand out.
3. Sylvie twirl dress: An effortless and elegant style made from ultra-luxurious Italian jersey.
4. Alina muscle tee: Substantial, super soft Peruvian pima cotton makes this more polished than your average tee (and how fun is the color?!).
5. Marsha earrings: Just the right amount of shine.
6. Natasha contrast turtleneck: The versatility of a basic turtleneck, but way more interesting.
7. Ayla travel jacket: Polished enough for the office but not overly corporate. Made from OrigamiTech, a designed-for-travel fabric that’s machine-washable and wrinkle-resistant.
8. Veja sneakers: Incredibly comfortable and go with everything. These have been my go-tos for years.
9. Allyn kick flare pant: A right-on-trend shape in the most heavenly ponte you can picture.
10. Curtis statement trench: Carmen Sandiego would approve.
11. Bia pleated trouser: Wide-legged and widely adored (these constantly sell out).
12. Filomina Friday shirt: Looks like a crisp poplin button-down. Feels (and stretches) like a tee.
13. Sarah Flint Perfect Pumps: An excellent version of a classic black pump. You can’t go wrong.

This mix-and-match packing list offers way more outfit possibilities than I have time to share, so I’ve highlighted just eight of my favorites below.

My ideal travel-day outfit has two key requirements: First, for obvious reasons, it has to be comfortable. And second, it has to use the bulkiest pieces on my packing list, thus saving me room in my carry-on. These outfits fit the bill. Having a chunky, textural sweater like the Kiki is such a luxury when you’re traveling, and—bonus—the black-and-white marled knit helps to hide stains. Stretchy kick-flare pants and crisp white sneakers are no-brainers since they’re comfy without being sloppy, and of course, a classic trench is the quintessential travel layer. If you want to look extra sharp en route, add a button-down that’s secretly as soft and stretchy as a T-shirt.

We’ll get to the office outfits in a minute, but first, let’s optimistically assume that your itinerary allows time for a little sightseeing. Opt for outfits that are casual but still polished enough that you wouldn’t be embarrassed if you ran into your boss. One fun idea (pictured on the left): Layer a berry-pink tee under a neutral crewneck sweater for a pop of color. Camel-colored pleated trousers add dimension, and sneakers keep the look from feeling overly corporate.

Another idea (pictured on the right): Start with a base of fitted, stretchy separates (like these kick flare pants and this cool contrast-piped turtleneck) and top with an oversized trench. Simple, neutral, and comfortable—but not boring.

When it comes to office looks, you have plenty of options. Here are just two of them. First, go for that same sweater-over-button-down look you wore on your travel day, but this time, pair it with trousers and pumps. Depending on the temperature, you could wear the sweater on top with your shirt collar peeking out, tie it around your shoulders, or omit it altogether. 

Idea #2: Wear the same turtleneck + kick-flare pant from your sightseeing day, but this time, add a cute cropped blazer on top. Pro tip: Swap the pants on these looks to double your outfit options.

Work dinners come in many forms, so I’ve included a formal option and a more casual one. A dressy dinner is the perfect opportunity to break out the elegant (yet also very cool!) Sylvie dress made from luxurious Italian jersey. Just add a trench, pumps, and earrings, and you’re good to go. (P.S. This outfit plus the Kiki sweater tied around your shoulders is another great option for the office.)

For more casual meals, wear the Ayla jacket as a top (it’s high-cut enough that it’s not at all scandalous) along with the Bia pants and sneakers. Oversized hoops make the outfit feel fun and evening-y.