How I Pack for Summer Travel in a Carry-On

'Tis the season for suitcase math.

Still haunted by a trip 11 years ago when I couldn’t fit my oversized duffel into the trunk of our rental car in Italy, thus significantly delaying the departure of our entire group, I haven’t checked a bag on a vacation since — not even for my honeymoon, which at three weeks was the longest vacation I’ve ever taken. I am and forever will be a staunch devotee of packing in compact carry-on luggage. I’ve tested out various approaches, including planning out all my outfits beforehand and planning out zero outfits beforehand. I’ve found that a combination of the two is ideal, albeit weighted toward the latter while sticking to my most versatile, re-wearable wardrobe items. (If an item can’t be worn as part of at least two different outfits, I’m unlikely to bring it). The math behind this equation requires a bit of personal trial and error based on what items you’re working with in your own wardrobe, but for me it nets out to roughly:

• 65% mix-and-matchable separates, i.e. tops and bottoms

• 10% dresses

• 10% workout clothes

• 5% underwear, socks, and swimwear

• 5% shoes

• 5% accessories

Below, I’ve attempted to apply this formula to a detailed rundown of what I would pack in a standard roller carry-on for a 10-day trip in a manner that is (hopefully) adaptable, or at least inspirational, across a variety of closets. For the avoidance of doubt, I also always bring a backpack in addition to a roller suitcase where I stow my toiletries, electronics, supplements, etc., and maybe one of the pairs of shoes depending on how crammed things are getting.

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10-Day Summer Travel Packing List: Suggested Items

• 1 long sleeve white cotton blouse. I usually bring an old style from Dôen that they don’t make anymore, although this style that’s currently in stock is really pretty ($198). Alternate secondhand option here ($67.99) and Etsy find here ($50.15). If you have a long sleeve button down, that works too.

• 1 short sleeve white cotton button down. I have a vintage one and another from a past collection at Éliou that I opt for interchangeably. The best place to shop for contemporary versions is often the men’s section. Here’s a good one from Urban Outfitters ($69) which apparently runs large FYI, and a second option from Perte d’Ego ($139.99).

• 2 cropped cotton tanks in a neutral color. Perfect for styling with high-waisted bottoms in cases where you’re going for a hint o’ midriff. I have a handful of these ($25) from Aritzia in different colors, but I also linked these ($35) from Kotn in a recent newsletter and a couple readers who bought them had very good things to report.

• 1 classic cotton tank in a neutral color. It’s weirdly hard to find reasonably-priced, classic 100% cotton tank tops these days. My favorite and the one I always pack on trips is from Entireworld, a brand that no longer exists but I predict will be resuscitated in some form at some point. In the meantime this one ($16.99) from Jockey looks good.

• 1 unfussy but still statement-y going out top. By “unfussy” I just mean it should be comfortable and look more beachy than urban. Other than that, the only requirement is that it should pair easily with any of the printed bottoms you bring, like silky pajama-style pants or a sarong — more on those items below. I love this ruffly secondhand Lanvin top ($87).

• 2 cotton midi skirts, ideally one that’s more tailored and another that’s fuller / gathered, both somewhat high-waist for styling purposes. I always bring a white denim midi skirt I bought from & Other Stories a decade ago (similar here from Dynamite for $59.95), and more recently a Ciao Lucia black high-waist skirt that is available on Poshmark for $135 with the matching top, or in a similar current season version here for $204.

• 1 mini skirt, preferably something tailored and slightly A-line that can transition from daytime to going out. I have and often pack this raw denim one ($165) from APC. There’s also a slightly longer version ($190) which might be better if you’re tall.

• 1 pair of white or black high-waist tailored shorts with belt loops. Regurgitating this Boden pair ($51.80) and this Bali Lane pair ($105) from my prior dispatch on shorts styling.

• 1 pair of white track or boxer shorts. Also regurgitating these from Dick’s Sporting Goods ($15.40). Sorry for saying “regurgitating” twice in the same newsletter.

• 1 pair of silky pajama-style pants. Any wide-leg, lightweight pants will do here, but I particularly love a silky pajama-adjacent option for summer vacation styling, especially if they have a fun print. I’ve been eyeing these ($350) from SEA but there are also some great secondhand options on The RealReal, like these from Margiela ($178.50), these from Gabriela Hearst ($310), and these from Le Sirenuse Positano ($124).

• 1 generously sized cotton sarong. Lisa Corti makes beautiful ones ($123). There’s also a bevy of cool block printed options on Etsy.

• 2 solid, neutral cotton or linen dresses, 1 midi-length and 1 mini. I like to bring one white one (my go-to white summer dresses are years-old from Dôen and LoveShackFancy) and one black one (also old, from The Gap). This black linen / cotton blend dress ($120) from COS definitely scratches the itch — though I would potentially get it hemmed so it’s really mini, depending on where it falls on you. I’m in love with this antique white cotton dress ($110) and would absolutely buy it for myself if I hadn’t already bought something else while doing market research yesterday for this newsletter 😆. I try to avoid indulging in that temptation too often, but it’s a hazard of the trade. Alternatively, this white dress ($198) from Anthropologie is also really pretty.

• 1 swim cover-up that doubles as a dress. I’ve been eyeing this one from Lisa Corti ($123) for a while. A short, kaftan-esque silhouette is ideal for multipurpose styling.

• 1 pair of sneakers that you can style with non-athletic attire. I recently wrote about travel shoes for The Cut so I’ll reiterate a lot of what I said there: I’m a fan of Nike’s Waffle and Daybreak models in this category because they have a graphic, vintage look that says “leisurely walk to go get ice cream” instead of “cardio,” which is the goal here. Color is an important contributing factor as well. I feel strongly that neutrals like black and cream should be eschewed in favor of something that really pops, so that the sneaker looks more ornamental than practical. This is important because it’s inherently practical — you can walk for miles in these without a shred of discomfort. Intentional, eye-catching color serves to visually offset their practicality to some degree and ensures the shoes look like a thoughtful part of your outfit instead of a utilitarian afterthought. I always wear these on the plane so I don’t have to devote suitcase room to them.

• 1 - 2 pairs of sandals. Assuming you have room for both, bring one super practical walking pair like Birkenstocks ($110) and one strappy but still comfortable pair that can be styled with evening outfits. I have a version of this style ($108) from Ancient Greek Sandals that I love.

• 1 pair of comfortable loafers. I have an old brown croco leather pair from Mansur Gavriel that I almost always pack on trips. These from Lauren Ralph Lauren ($224.99) are very similar. If you’re buying new ones just make sure to break them in before you travel with them.

• A pair of black or sunglasses with a classic frame. I have and wear this style ($95) from Warby Parker constantly, but recently I’ve also been admiring this slightly more rectangular shape.

• A couple pieces of colorful jewelry. I usually opt for necklaces here — ones that loudly proclaim “I’m on vacation!!!!” much in the way that a frozen beverage decorated with a tiny paper parasol might. This vintage red disk necklace with a juicy center bead ($25.20) is so fun, and as we’ve discussed, you can’t go wrong with a 10mm turquoise rondelle style ($126).

• A couple pieces of chic minimalist jewelry. Per my recent fashion jewelry deep dive, gold coins like these ($19.91) and baroque pearls like these ($99) are foolproof options. I love this sterling silver disc necklace ($92), too.

• A fabric i.e. packable hat. Kassandra, the artist behind Kasmaria, kindly sent me one of her sweet small-batch Liberty of London hats ($175), which I pack and wear often while traveling. Alternatively I love these from Call It By Your Name, and this one ($31.99) from Madewell.

• A fabric i.e. packable tote. I always pack ultra-lightweight block print totes like these ($9.49 for 5) or these ($20.08) on trips because they fold up to practically nothing and are just the right size for carrying around a wallet, phone, and bikini.

• A colorful silk scarf. Great vintage options about on Etsy. I’m obsessed with this one ($49.93).

• A brown belt. This one ($105.18) looks perfect.

• A fun hair accessory like a cool scrunchie or colorful claw clip. I like to pack a frilly scrunchie like this ($11.98) to wear around my hair in a bun. Just for fun.

• 2 swimsuits. I always pack my favorite bikini from Galamaar, which I wrote about a few months ago — the Simone Top ($156) and High Kick Brief ($124). It comes in a bunch of colors but I like turquoise specifically because I can style it with my turquoise rondelle necklace for a matchy-matchy moment. It’s the little things! The second suit I typically pack is an Eres bikini I bought about a decade ago during a sale. I’ve gotta say — it’s really held up. The Outnet tends to be a great source for on-sale Eres, i.e. the gray bikini pictured above — top ($96) and bottoms ($68).

• Underwear. I’m passionate about Knickey ($17 a pair), if you’re in the market for a recommendation.

• Socks. My holy grails from Hue ($11.99 for 6), naturally.

I’ll spare you from in-depth detail here because my workout clothing choices offer absolutely nothing in the form of inspiration, but my favorite athletic shorts I’ve ever owned are these from Outdoor Voices. I think they’re exorbitantly priced for workout shorts, though ($58!), so I’ve been attempting to find a decent dupe. I bought these New Balance ones ($19.33) and they’re the closest I’ve found, but they’re not as good. Will continue searching.

10-Day Summer Travel Packing List: Suggested Outfits

Bon voyage!

xo Harling