A defining feature of mine is that I will do anything to get a new stamp in my passport. In the past year alone, I’ve been to Miami, Nantucket, Denver, San Diego, Houston, Stockholm, Sao Paulo, and Belize City, with more trips planned. It’s a lot of fun, but traveling can also be a challenge. I’ve spent hours packing because I had no idea what to bring. What if I suddenly go dancing? What if it’s cold outside and I forgot my light jacket? There are just too many uncertainties.
But with lots of practice, I’ve refined my approach and now have a few travel tips I can share: For example, I’ve heard so many travel horror stories that I’ve stopped checking luggage altogether (though I do use AirTag), and instead I pack light, choose versatile clothing, and use compression packing cubes to stay organized.
I treated myself to a shopping spree at the start of summer, and many of the items that were great for my trip are on sale now. Now that it’s getting colder outside, I can save these pieces for next year, or wear them when I travel to warmer places this winter. Here are some of my favorite pieces that can be dressed up or down, perfect for those days when you don’t feel like getting all dressed up, but have dinner reservations somewhere nice.
Everlane shirt dress
Everlane
A shirtdress is always a good idea. I’ve traveled with bodysuits and skinny jeans and they were always uncomfortable. The last thing you want is something that fits you when you’re eating pounds of gelato or sweating in the hot city. This breezy linen shirtdress is stylish, put together, and so comfortable it feels like you’re wearing nothing at all.
Madewell pintuck slim pull-on pants in satin
Madewell
Satin pants are another travel secret I’ve discovered. Unlike jeans or trousers, which take up too much space in your suitcase, this style rolls up easily into packing cubes and can be paired with almost anything. They’re a travel essential.
Anthropologie Love Knot Slouchy Bag
Anthropologie
Ideally, I’d have one bag to match each outfit, but for practical reasons, I stick to just one. This oversized tote bag is perfect for flights, strolling around town, or even a nice dinner, and it’s carry-on friendly.
Grey Ven Price bomber jacket
Rotate
Recently, I wanted to look better on the plane (just in case I meet someone cute), so I upgraded my travel jacket. I used to wear a hoodie, but now I opt for this faux leather bomber jacket. Not only does it make me look more classy, but I can wear it the whole trip. My old, tattered sweatshirt from college just doesn’t look right in a fancy restaurant or strolling along the Seine.
Vineyard Vines Silky Slip Skirt
Grapes in a vineyard
A good slip skirt is incredibly versatile and can be worn with almost anything — it looks great dressed up with a silk tank top and heels or casual with a graphic tee and sneakers — and it takes up very little space in your suitcase.
On Cloud X 3 AD Sneakers
Zappos
When I’m in a new city, I love to walk miles. It’s cost-effective and allows me to see a lot. I’m a big fan of the On Clouds because they’re stylish enough to wear with jeans or a skirt, practical enough to walk in comfortably without getting blisters, and can also be used for running or training in the hotel gym.
Below are some of the fashion essentials that made a difference during my travels.
J.Crew Crinkle Drawstring Midi Skirt
J.Crew
GAP Linen Blend Utility Romper
gap
Abercrombie linen-blend T-shirt dress
Abercrombie & Fitch
