It’s impressive when your cover up is actually sexier than your bikini. Gold tone rings provocatively hold this Michael Kors Collection dress together, but on a beachy vacation, you could even wear it to dinner (just have something on underneath, please!). This is as glamorous as cover ups get, and considering I prefer cocktails and lounging to laps in the pool, glamour is what I’m going for. You can’t overdo it, though. Skip the heels and slip into some Jimmy Choo cork wedges (at Saks Fifth Avenue for $465) – they’re my trusty travel companions each and every summer. I also pack an Eric Javits hat. This cutout-trimmed number (at Saks Fifth Avenue for $295) is so much more interesting than the average straw hat. The finishing touch? Fendi’s drawstring tote (on Farfetch for $1,211.48). Between the perforation, red strap, and cotton drawstring fastening, it seems made for summer fun. Available on Shopbop for $406.