Cheryl Shops

 It's peak summer travel season and hopefully you've got a big trip coming up. (I do next month!) When I vacation in the summer—or anytime I go somewhere warm—I tend to pack mostly dresses. I don't want to think too much about putting outfits together when I'm trying to relax and decompress, so there's something so easy about throwing on a dress and going about your day (or night). I definitely dress a little differently when I'm on vacation, but there's something kind of glamorously escapist about embracing the fabulousness of resort wear. Think more carefree boho vibes, less polished minimalism. I have several go-to brands that capture that sprit so well; here are my 5 favorite dresses to wear on vacation. 

Amazon The Drop slip dress

I was technically on staycation here in San Francisco when we shot these (hence the denim jacket), but this slip dress is a frequent travel favorite—I've worn it everywhere from Vienna to Honolulu. It also packs down into almost nothing, making it extra carryon-friendly. My one caveat is that this dress is polyester and doesn't breathe well, so I don't recommend wearing it somewhere you're going to be sweating a ton. The other thing is that you need to wear a strapless bra with it, but that's often the case with strappy slip dresses. Otherwise, I think this one has such a nice body-skimming fit, and it looks much more expensive than it is. I'm wearing a medium, so I'd say it fits true to size. It also comes in a gazillion colors, if you're not partial to blue.

OUTFIT DETAILS: Gap denim jacket | The Drop slip dress | Bottega Veneta Jodie teen | Isabel Marant sandals (similar here)

Devotion Twins Petra dress

Speaking of dresses that come in a gazillion colors, you can get a Petra dress in everything from subtle white-on-white to multicolored neon. I personally prefer a white-and-bright color combination (I'm wearing mint in these photos) for a just-off-the-yacht kind of feel. One thing to note: this dress is quite voluminous, so it's not always the wisest choice if you're trying to take only a carryon, but then again, you can wear it on the plane over a pair of skinny jeans or leggings. It also runs quite large; I'm in a small, which is fitted in the arms and super flowy everywhere else. 

OUTFIT DETAILS: Devotion Twins Petra dress | Isabel Marant mini Skano bag (full size here)  | Isabel Marant sandals (similar here)

Greek Archaic Kori caftan (current version) 

Yes, that name is a mouthful, but it definitely sets the tone for a certain kind of vacation dress, doesn't it? I discovered this brand on Instagram a few years ago and I think their dresses are gorgeous, especially if you go for the metallic thread, which of course I did. They run entirely huge (I'm in a small here), but that's exactly how they should be. These dresses are made for sipping a spritz on the deck after a good swim, and they look fabulous doing so. 

OUTFIT DETAILS: Greek Archaic Kori caftan (current version) | Mango raffia tote (current version) | JW Anderson sandals 

Juliet Dunn off-the-shoulder dress

If Greek Archaic Kori is a yacht docked in the Mediterranean, Juliet Dunn is a posh British lady letting loose in Ibiza. Her dresses are made of gorgeously printed Indian cotton, with or without sparkly embellishments (I prefer the bling for nighttime). They are not cheap, however, so I recommend saving a search on The Real Real, which happens to have the exact one I'm wearing (it's "one size fits all," which is exactly the kind of thing a brand designed for posh socialites would pull). 

OUTFIT DETAILS: Juliet Dunn off-the-shoulder dress (also love this one) | Isabel Marant sandals (similar here) 

Monica Nera Maya dress

This is the perfect dress for the last few days of vacation, at which point you've overindulged in everything and are now carrying a food-and-alcohol-bloat baby. I most recently wore this one to brunch in Miami and it was perfect for slupring down bellinis and oysters without anyone being the wiser. What I love is that you can adjust the gathers to flatter your shape. This dress is also incredibly forgiving; I'm in a medium but probably would have been more than ok in a small. It also comes in a bunch of colors if pink is not your cup of tea—I think the navy in particular is super chic. 

Monica Nera Maya dress | Staud Bissett bag (love this one) | Sarah Flint Mirjana wedges