What to wear: Onia bathing suit, Buy It Now at Onia, $130; Gitman Brothers Vintage popover shirt, Buy It Now at Need Supply, $105; Shades of Grey by Micah Cohen sweatpants, Buy It Now at Shades of Grey by Micah Cohen, $179

A weekend trip is a huge moment for a new couple. You may have been able to survive brunch with her girls, but a weekend trip lasts much longer than two hours and you can't drown your sorrows in bottomless mimosas. For these few days, you're going to want to dress and be as relaxed as possible so that the two of you can bond over irie vibes, instead of stressing out over a flight delay.

That being said, this isn't spring break. Ratty tanks and extra-long surf trunks aren't going to cut it. Even if you have no intentions of swimming in the choppy ocean, you don't want to be mistaken for a sloppy surf-bum at the tiki bar. Use this as a chance to inject some crispiness into your vacay wardrobe, and the next first weekend getaway with the next girl will already be half taken care of.