How to Navigate Every Kind of Resortwear Dress Code

Full discretion: I'm a member of the unfortunate community of individuals who absolutely cannot properly pack for vacation. At a minimum, I spend nearly three months of the year traveling, yet I haven't mastered the art of curating a mini wardrobe that's weather-appropriate, event appropriate, and full of all the essentials. Without fail, I either pack too little (and find myself with only three pairs of underwear and no toothbrush for a two-week trip) or too much (and am left with a suitcase five kilos over the limit).

The worst-case scenario? Arriving at my destination and realizing I've failed to pack stylish outfits that suit the dress code of the resort I'm staying at. I once packed my most fashionable assortment of items for a trip to Dubai, only to find out that none of my pieces suited the strict dress code. That being said, resort dress codes can be difficult to interpret, thanks to confusing categories like "elegant casual" (a total oxymoron, IMO). Thus, today I thought it would be useful to curate a guide to resort dress codes.

The hope is that it’ll serve as a reminder not only to pack underwear and a toothbrush (very important), but perhaps a wrap and evening dress as well, given the dress code. Read on…

"Resort casual" is my favorite dress code—this is an "anything goes" mentality typically appropriate for daytime wear. These are the outfits you wear while lounging by the pool or on the beach, or perhaps while grabbing a midday lunch at the beach bar. Comprised of maxi dresses, beach cover-ups, and strappy sandals, this dress code is a break from the stylish, put-together, well-thought-out outfits we fashion girls concoct on a daily basis. That doesn't mean there isn't a place in this dress code for fashion, however; some of my favorite pieces make an appearance here in the form of giant floppy sun hats, caftans, and a Loewe tote.

This dress code usually refers to a casual dress code, but for eveningwear. It's what you'd wear when you're going for a weeknight dinner with girlfriends or a weekend brunch. Light, airy, and fun, it's sophisticated without feeling stuffy. The ideal "elegant casual" look consists of a casual summer dress, paired with a light scarf wrap and a pair of slingback mules. This dress code usually comes into play when dining at the resort or sipping on a fresh gin and tonic at the resort bar pre-dinner.

While the difference between "eveningwear" and "elegant casual" can be understated, it is real. Instead of a weeknight dinner, think a weekend date night with your S.O. Rather than a casual summer dress, opt for slightly more formal attire like a ruched silk dress or a flowing midi skirt paired with a blouse. Accessorize your look with fine gold jewelry, heeled strappy sandals, and a wrap for a chic evening on the resort.

This is the showstopping outfit your inner fashion girl has been waiting for. Don't be afraid to pull out all the stops when you see "formal attire" in the dress code. Though less dressy than this standard may be on the mainland, cocktail-party attire is entirely appropriate. Typically reserved for holidays such as New Year's Eve, as well as destination weddings, anything ranging from a maxi dress to an evening gown or pant suit will suffice. Don't be afraid to get creative—vacations are the time to experiment!

Up next, Anna Wintour reveals her five favorite brands of fashion month.