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Which Vacation Friend Are You?



Photo-Illustration: by The Cut; Photos: Retailers

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No matter where you’re going, vacation plans usually require condensing your wardrobe essentials and everything else into a carry-on or weekender bag. Trust us — we know. Since there’s so little space and much to pack, we’ve consulted our team, seeing as we’re always traveling for work, play, and various Fashion Weeks and have somewhat perfected the art of the vacation wardrobe (and not losing our luggage).

We’ve rounded up some of our favorite fashionable swim and resort brands, walkable shoes, and bags. To make it even easier, we’ve broken it down into super-specific categories: vacation archetypes. Are you the friend who arrives at the airport hours ahead of takeoff, the friend who’s not going that far, or the actual mom? Read on to see our picks.

You’re the planner
You’re the party friend
You’re the mom friend
You’re the actual mom
You’re the photographer
You’re the local

You’ve been coordinating this trip for months, you were at the airport hours ahead of time, and you have TSA PreCheck. Your itinerary is solid, and your outfits are sensible. Go for shoes you can also wear to the airport, outfits you can also wear to the beach, and dresses you can wear with sneakers, flats, or heels.

A high-drama dress perfect for dinners, photo ops, and plenty of special events after your vacation. With a light sheen, lots of color options, and even more size options, you should grab this dress before it goes viral.

Low-heeled sandals from French-girl brand Sézane are perfect for avoiding blisters.

The one-size-fits-most option is stretchy and doesn’t have that shiny swimwear look, so you can wear it as a top, too.

Yes, you brought sunscreen and sunglasses, but this wide-brimmed hat adds another layer of sun protection.

“ASICS are so incredibly comfortable. They’ve survived my ambitious step goals in Paris, Mexico, and Spain without blisters or getting all stinky (if you know, you know),” senior shopping editor Bianca Nieves says. “I highly recommend. I’m usually a Gel-Kayano wearer, but these GT-2160s are on my to-buy list.”

When the vacation plans hit the group chat, you already had a handful of hot spots to check out. You’ll want a minidress you can dress up or down, and you won’t need any “practical” accessories — your “mom” friend’s got those covered.

Sheer and plunging, this “It”-girl favorite is perfect for nights out and layering it over your go-to pieces in the daytime.

This brand has been on our radar for a while, and it’s a favorite of fashion and beauty writer Asia Milia Ware. The hand-crocheted dress is sexy, stretchy, and easy to wear. Feel free to layer it over swimwear or make it your next going-out dress.

Somewhat practical and very on theme, this palm-shaped bucket bag can fit your phone, wallet, and lip gloss.

These sandals look much pricier than they actually are. With a rose detail on the heel and straps that tie up the ankles, you can skip the extra accessories.

Not to be confused with the “planner” friend. Your going-out bag is big enough to carry everyone’s phones and Band-Aids, hand sanitizer, and mints — did you need anything else? Save some space in your carry-on with sets you can mix and match and all-purpose bags.

Worry less about planning your outfits or packing and more about soaking up the sun in this easy-to-wear dress.

The set alone is pretty pricey, but you can grab one of these pieces on its own, like the top, and mix and match with denim or linen.

A Cut-staffer favorite, Fréja’s durable vegan-leather bags are more spacious than they look. The ’90s-inspired silhouette doesn’t look like a vacation bag, which is why it’s the perfect buy: You’ll use it long after your trip.

“I’ve been anti-flip-flops for most of my life. These changed my mind. There’s something about the square toe that elevates your whole look,” Nieves explains. “I took this pair with me last year to Portugal, and they survived Lisbon’s hilly streets. Now they are a must every time I travel back home to Puerto Rico.”

The kids are in tow, maybe your in-laws are coming, and the venue is family-friendly — whatever the case, your vacation is rated G. You want something covered up but still chic. Sure, you’re not bringing out the thong bikini, but you still want to show some skin and keep cool.

Stay all covered up but still keep cool with this poplin button-up. The stretchy top has an adjustable open back so you don’t show too much skin unless you want to.

Maxi dresses don’t have to be boring, and this pleated one from Sandro is anything but. The flowy pleated dress has a low back so you get lots of air.

You’ve probably had your eyes on a pair of mesh flats for a while, and these are a good option that won’t break the bank. Your next vacation is a good time to finally grab them; unlike heels, they’re perfect for squeezing into your carry-on.

You know everyone’s angles, and for that, we’re grateful. However, be sure to pack something photoworthy, too. You belong in front of the camera at least once.

Protect your eyes, and add something special to your outfits. “Sunglasses are a must for me. I always gravitate toward Poppy Lissiman’s frames because they are the right combination of trendy,” Nieves explains. “Normally, my vacation wardrobe is pretty simple (three bottoms, three tops, and three shoes that I can perfectly mix and match), so I like to incorporate some oomph with my sunglasses.”

A favorite from Cut staffer Morgan Evans, Baobab offers shiny and shimmery photo-ready swimwear and separates, so you can also remember to take a few vacation pics of yourself in a standout piece like this glittery purple option.

House of Aama is one of Ware’s favorite brands for vacationwear, and the collab with Free People is worth buying. This flowy, printed midi skirt is perfect for mixing and matching with basics and bikini tops. Grab the matching top, or dress up some plain white tank tops you already own.

Your vacation plans might be a short car ride away, but that doesn’t mean you can’t pack a new outfit or two.

Because you need something nice to wear with those cutoff shorts, this adjustable cotton blouse is great for dressing up sandals or sneakers.

There’s no shortage of rooftop pools in NYC, so you don’t have to save all your nice swimwear for trips abroad. Riot Swim, a favorite of Ware’s, makes cheeky swimsuits with cool silhouettes that double as bodysuits.

If bubble hems have been on your list, here’s an easy way to get into the trend. Made of airy cotton, you can pair this dress with sandals all summer and add a cardigan as it gets cooler.

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