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Beach-to-Dinner Sandals
Pack a pair more polished than flip-flops and you might not need to switch your shoes all weekend. Lay out in them at 1 pm, go out in them until 1 am. Simple.
Wrinkle-Resistant Dresses
Pick forgiving fabrics (already-drapey jersey, crumply chiffon, stiff chambray, NOT silk) and you won't have to hang those dresses by a steamy shower trying to get them to look presentable (never really works that well, does it?). Ideally, opt for day-to-night options too, like that black dress: it could easily be worn loose and low-key over a bathing suit, then belted and worn with heels for an outdoor party.
Non-Fussy Jewelry
It'll turn those easy dresses that you packed into fancier-looking outfits, which is key. And if you pick pieces that are pretty but not too blinged-out and sparkly, you can wear them by the pool and look glamorous and cool, not like a Real Housewife.
Well, duh.
A Warm Layer
Even if it's hot where you're going, it'll probably get cold in the car/train/plane on the way there. (Or in the overly-air-conditioned supermarket, restaurant, movie theater...). Just pack one.
Two Swimsuits
Is there anything worse than having to peel on a still-damp-from-yesterday swimsuit because everyone's going to the beach right this second and you don't have 40 minutes for a dryer cycle? No. Come prepared.
Versatile Tops
With daytime jeans and sandals or nighttime skirts and heels, the tops you pack should be versatile, since it's not like you have room for a zillion options. Think slightly prettier than a t-shirt, but not a full-on "going-out top," whatever that means.
Faded Denim
While everyone else is busting out their white denim, you'll look appropriately start-of-summer-y—yet slightly fresher—in these. (Plus, with cool nights and air-conditioned spaces, you'll want pants on hand too, not just a little sweater or light jacket.)
Beach Blanket
Takes up way less room in your weekend bag than a towel and spreads way wider once you unpack it, staking a much bigger claim in the sand. (Plus, wrap it around your waist and it doubles as a cover-up. You need one.)