Do you ever imagine yourself on a trip before you go on it? I do. Most importantly, I’m imagining the perfectly curated vacation outfits I’m going to wear.
For someone who spends an enormous amount of energy trying not to spend money, I spend an equally ungodly amount of time online shopping. Unfortunately – or fortunately, depending on the way you look at it – I have quite the talent for it.
I’ve curated my personal capsule travel wardrobe of items that always end up in my carry-on, regardless of what time of year it is and what’s on my itinerary. Outdoorsy trips are the exception; those require an entirely different list. But whether you’re visiting a city, a rural town, a beach escape, a mountain getaway or anywhere else you may need a pair of jeans or a purse, this list is a fabulous place to start.
I know what I like, and that’s comfort and convenience without sacrificing my personal style. After patiently curating my go-tos over the years, the resulting list leaves me plenty of room for fun and colorful complementary pieces, and all sorts of ways to dress up or down.
Bottom line: it’s fun to dress up on vacation, but you don’t need to buy a new wardrobe (or any of the things on my list) to do it. Next time you’re packing for a trip, take note of which items you find yourself reaching for first. Also, I love asking others about their packing must-haves, so please share yours in the comments.
1. An elevated white t-shirt
Don’t interpret elevated as expensive. When I shop for fashion’s most basic invention, I want a flattering cut and soft, quality material.
It sounds like I’m overthinking a white t-shirt, but there are three I love and wear religiously. On the lower end of the price spectrum, Gap’s VintageSoft tees already feel worn right out of the package. I also love (and am currently wearing) this one from Los Angeles Apparel. FYI, I read the reviews and sized up for a regular fit. Lastly, I took advantage of Reformation’s first-time purchase discount and finally went for this soft-as-ever, fitted-but-not-too-fitted tee I’d been eyeing for over a year.
2. Black cropped flared pants or leggings
Like my fellow editor Brekke, I hardly work out on vacation and, therefore, almost never wear workout clothes when traveling. The one exception, which I always wear on the plane, is this pair of cropped flared black leggings from Lululemon. The silhouette is always flattering, and the sassy little kick flare looks so put-together. You could also do pants, like this ribbed pair from Donni or this sweater-like pair from J. Crew (which I also own and wear often). Personally, there’s no way I’m wearing “real” pants for a plane ride that’s over 2 hours.
Note: The Lululemon pair is cropped because I bought the petite size, and I’m a 5’7” gal. But for my shorter friends who want that cropped look, I’m also eyeing this similar pair on Beyond Yoga, whose Spacedye fabric is so soft yet sturdy.
3. Bootcut jeans
They are the easiest cut of denim to dress up and, despite their name, look amazing with any shoe. Rolla’s Duster bootcut jeans are my favorite, and I always get asked where this pair specifically is from. A black pair is also easiest to transition between day and night.


4. A nice white blouse
Very open to interpretation, but another day and night option. I own a few variations, and the best part is it’s a thrift shop staple; my favorites are a no-label vintage Peter Pan collared button-up I picked up at a vintage shop for next to nothing, and the Henri top from DÔEN. It’s a pricey piece, but I think my cost per wear at this point is <$1.
Tip: I’ve seen the Henri top pop up often on Poshmark, so try digging there, too.
5. A little black lightweight cardigan
Cardigans are very important for travel. Throw one on to change up an outfit you’ve already worn on the trip and keep it handy for the inevitable chill on the plane. I love my merino wool one (also from DÔEN, but since discontinued) because it’s soft, lightweight and temperature-regulating. Here’s a similar one from J. Crew that’s currently on sale.
6. New Balance sneakers
I’m being strict on the brand here. I walk a lot, both for exercise and in everyday life, therefore I’ve tried a lot of walking shoes. None has excelled more in support, style and price point than New Balances. I’ve had this pair of 1906Rs since May, and they’re still in tip-top shape, despite my average daily step count of >9000 this year.


7. A pair of Mary Janes
I don’t travel with heels unless there’s a planned event where I’ll need them. Why would I make my poor feet uncomfortable on vacation? I’ve found Mary Janes to be the comfiest and most versatile shoes, and I often travel solely with a pair of those and my New Balances. I’m eternally loyal to this pair from Sam Edelman, which I own in three colors and have convinced so many women in my life to buy. No breaking in required.
8. Bombas socks
I’m pretty anti-toes out when I’m home in NYC. Open-toed shoes are for the pool and beach. I like to continue working on my sock tan when I travel with Bombas. They’re a cult favorite for many reasons – comfort, quality, pretty colors. They have a 20% off first-time discount, too. Their quarter socks are the perfect height.

8. Calzedonia cashmere-blend socks
When I’m not in Bombas, I’m wearing these, so obviously, I’m traveling with them, too. I alternate between two pairs from Calzedonia: this ribbed pair and these ankle socks. They’re so soft (you could play a drinking game for every time I’ve said “soft” or “comfortable” in this post) and sophisticated.
Tip: Calzedonia almost always has a sale, so I recommend waiting for the next buy-3-get-3-free sock deal.
10. A crossbody purse
Crossbodies are best for travel because they have plenty of storage, are less likely to weigh down your shoulder and are easiest to keep secure should you travel somewhere where pickpocketing is a concern. My best advice is to look for something secondhand and leave your “nice” bags at home.
Tip: For leather bags that need some love, leather cleaner and conditioner are inexpensive and an easy way to bring them back to life.
And that’s my traveling closet tour, thanks for reading!
Ta ta for now,
Ann Douglas








bombas 🤝 travel girls
Any chance of doing this for guys?