I Went to Seoul, Miami, and Chicago This Month—Here's Everything I Wore Along the Way

It's been a busy month. The first weekend of May saw me pack up my TUMI carry-on and head to Miami for four nights for the F1 Miami Grand Prix. Ten days later, my larger TUMI checked bag got its time in the spotlight when I filled it up for another four nights away from home (i.e., New York City), this time to Seoul, Korea. Five days after that, I packed some essentials, a wedding guest dress, and some heels into a duffel and headed to Chicago for a wedding over Memorial Day Weekend. That's all to say that I've racked up an unusually large number of airline miles in May, and worn a lot of outfits along the way. As such, I figured I'd share my packing-related findings from my time away. Wondering what to pack on multiple trips? You've come to the exact right place.

Ahead, discover which pieces from my closet went on multiple trips this month, which ones received the most compliments, and different ways to wear simple items over and over. You'll also find packing tips from a frequent flyer (me), including my thoughts on packing cubes, rolling clothes versus laying them flat, and long travel-day outfits. It's all to come if you just keep scrolling.

Travel Outfits

Clearly, I'm at the airport a lot, which also means that I've made a lot of mistakes when it comes to travel outfits. I've worn jeans that don't budge during a five-hour flight, accidentally forgotten socks and had to walk through the security line barefoot, and chosen wrinkle-prone pieces for my in-flight attire. Traveling by plane is stressful enough as it is, between the lines, delays, and that whole flying through the air part. Wearing a bad outfit is easy to avoid and makes a big difference when it comes to your travel-day mood and mindset. My solution? Wear basically the same thing every time you travel. For every trip I've taken during the month of May, whether it involved a two-hour flight or a 16-hour one, I've worn the same pair of Veynd yoga pants, an oversized white T-shirt (from either Madewell, Agolde, or Citizens of Humanity), and my go-to brown car coat from FFORME. On my feet are usually sneakers—whatever pair I plan to work out in during the trip—and my bags are almost always a TUMI aluminum suitcase and some sort of too-big tote bag, either from Longchamp or COS. It's a combination that's yet to fail me.

tumi

International Carry-On

Longchamp

Travel Bag Expandable

FFORME

Shatter Light Overcoat

Packing Tip 1: Packing cubes are your friend

I used to think packing cubes were a hoax—something travel influencers sold you on that didn't actually work. I was wrong. They make the biggest difference, especially when you're traveling for a long time with just a carry-on suitcase.

BAGAIL

10 Set Packing Cubes

What to Pack for Miami

Miami can be a hard place to pack for. Usually this time of year, it's extremely hot and humid, so the lighter-weight the fabrics you pack are, the better. In the spring, however, rain is prevalent, so it's best not to pack only white poplin or linen everything in the off chance that a shower arrives and either knocks up a ton of mud on your formerly pristine white linen trousers or that poplin shirt you love becomes completely sheer. It's also a fun, vibrant city, making it a great place to bring out your louder, statement wardrobe items. Lastly, if you're going for the Grand Prix, whether you're sitting in the Paddock Club or attending with a general admission ticket, you must consider bag requirements and prioritize comfortable footwear.

Though I don't suggest only packing white poplin pieces for a trip to Miami in the spring, that doesn't mean you shouldn't pack any. On the contrary, a white poplin dress like this one from Tibi is one of the best pieces to wear on a hot, humid day in the Florida heat, especially at the track, where you're out in the sun for long periods of the day without shade. I've arguably never been asked about a clothing item more than I was at the race track in this dress. It's eco poplin, which is great because it wrinkles less than normal poplin, plus, it shows sweat far less. The back is adjustable and completely open, and... it has pockets!

Tibi

Eco Poplin Strappy Dress

When I found out that we were going to eat at Sexy Fish in Miami, I knew exactly what dress I had to pack for night one. Anyone who's been to the restaurant will tell you that this is basically the dress equivalent of the famous ladies' room in the establishment, which is equally pink and iridescent. The dress, a new hot pink version of Tory Burch's viral yellow dress from the S/S 23 collection, is quickly becoming a favorite among fashion people this season, and has already sold out in multiple sizes, so if you want one for your next trip to Miami (or elsewhere), act fast.