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 in Seoul, South Korea. Five days after that, I packed some essentials, a wedding guest dress, and heels into a duffel and headed to Chicago for a wedding over Memorial Day weekend. That’s all to say that I racked up an unusually large number of airline miles in May and wore 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 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, 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 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 with the lines, the 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 oversize 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 has yet to fail me.

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.

What to Pack for Miami

Miami can be a hard place to pack for. This time of year, it’s usually extremely hot and humid, so the lighter the fabrics you pack are, the better. In the spring, however, rain is prevalent, so it’s best not to pack only white poplin and linen everything on the off chance that a shower arrives and either knocks up a ton of mud on your formerly pristine white linen trousers or renders that poplin shirt you love completely sheer. It’s also a fun, vibrant city, making it a great place to bring out your loud, statement-making 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 never been asked about a clothing item more than I was while wearing this dress at the racetrack. 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!

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. If you want one for your next trip to Miami (or elsewhere), act fast.

Unless you’re in Monaco, where qualifying is the most important day of the race weekend, you’ll probably want to save your best look for race day, which is why I held off on wearing this Tory Burch S/S 25 runway look until the Sunday of my trip to Miami. The swimsuit-like material of this bodysuit made it perfect for a warm, humid day at the track, and the flame print on the pants just felt right for racing.

What to Pack for Seoul

My packing list for Seoul was far less extravagant and bold than it was for Miami. My goal for my outfits was versatility and an overall look that was chic and simple. A white poplin skirt, wrinkle-proof black trousers, and a plaid button-down shirt were my most-worn pieces, and tried-and-true tanks and tees, multipurpose outerwear, and some going-out tops acted as supplements. The weather was slightly chillier and more rainy than I expected it to be this time of year, so I was happy to have adaptable items and two coats alongside me on my long journey to South Korea.

First things first, I don’t think a better pair of travel pants exists. These are the Damian Pants by Kallmeyer, and because they’re crafted out of twill, it’s basically impossible to wrinkle them. At the same time, they’re stretchy (sort of like track pants), but appearance-wise, they look like super-elongating, hyper-tailored trousers, making them easy to dress up for formal dinners and cocktail parties. I wore them during the day and the evening during my trip to Seoul, styling them with various top options, including this plaid Tory Burch button-down shirt, a draped one-shoulder top from Abadia, and a silk halter-neck blouse from Liberowe. As you’ll see later, I also brought them to Chicago, wearing them to a pre-wedding cocktail hour with a black Khaite top. Just know that they’re long, so if you don’t like the look of cuffed pants or find high heels uncomfortable and hard to walk in, prepare to head to the tailor.

This white Lafayette 148 skirt has joined me on many a vacation, including my last two summer vacations to Italy and Spain. It’s been on multiple trips to Miami and Los Angeles and probably other places I can’t even think of at the moment. It wrinkles in the chicest, most subtle way, so I don’t even have to iron it. It looks nice while still being comfortable and easy. I wore it twice in Seoul, including here with a white Zara tank top (that I have in two colors) and sandals. I also wore my brown Fforme coat on top, though I took it off for this photo.

Packing Tip 2: Always Use the Roll Method

I can fit a shocking amount of clothes when I roll my pieces up into tiny cylinders like pigs in a blanket and puzzle them together inside my packing cubes like an IRL game of Tetris. You can also put anything fragile inside of these rolled-up tubes of clothing to keep it from breaking.

What to Pack for Chicago

Chicago, being where I was born and raised, is an easy place to pack for. I know how the weather can turn on a dime and how it can be burning hot in December and freezing in May, so I always come prepared. That said, I was only in the city for a few short days over the long holiday weekend and had to come prepared for a formal wedding and cocktail event the evening before. I fortunately already own a number of dresses fit for the dress code, so I grabbed one that doesn’t wrinkle—an elegant high-neck column dress from Bernadette—and heeled sandals from The Row. For the night before, I wore my trusty black Kallmeyer trousers with the same heels and added a strapless peplum top from Khaite’s S/S 20 collection. Easy. The rest of the trip was spent at my boyfriend’s parents’ house, so I lived in button-down shirts, knits, and a trusty pair of white carpenter jeans from Banana Republic.

As I’m sure you can already tell, plaid is one of my favorite prints at the moment, and because of that, this shirt is getting a lot of wear time. I love how easy it is to style and how I can wear it to something as casual as an outdoor lunch in the Chicago suburbs or as formal as a nice dinner in Seoul. Here, I styled it with loose white jeans and black accessories, including my trusty COS Bowler Bag, Studio Amelia heeled thong sandals, and a black belt from Aritzia that looks like The Row. (Just saying.)

We arrived in Chicago on Saturday night, and straight off the plane, we headed to Greek Islands aka my favorite restaurant on the planet. I changed out of my plane clothes at the airport, swapping out my yoga pants for Kallmeyer trousers and my white tee for this Khaite peplum top. (On top, I wore a Sézane cropped car coat.) Following dinner, we headed to our pre-wedding cocktail hour. There wasn’t a dress code, but I always err on the dressier side for things like that, just in case.