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Tank Dresses
The good ones are as comfy and hot-weather-ready as a long t-shirt. You'll want a dozen of them for one-and-done dressing on annoyingly hot days, so buy them at a price point where you can actually do that.
Panama Hats
It's silly to spend a ton of money on something you'll wear so seldom, especially when you usually can't tell the $40 ones from the $400 ones.
White Jeans
They never manage to stay immaculate for long. You'll probably grass stain them or ketchup stain them or both, so it's good to have a pair you love but isn't a $200 investment.
Striped Tees
Because you can never have too many.
Basic Sandals
Don't worry about treating your wear-with-everything sandals too preciously. If they're going to get wet from summer thunderstorms or pool splashes or salty ocean water, they're going to be cracked and warped by September, so just buy cheap ones. You'll have more fun in them.
Silk Camis
You'll need something to tuck into party skirts and wear underneath sheer lace tops. Silk camis are great for that because they look fancier than plain jersey ones, but still, there's no reason to spend that much more for them.
Sunglasses
Let's be real, you'll probably lose them anyway.
Baseball Tees
They're sporty yet sort of adorable and they're basically the ideal weekend t-shirt. Plus, they always look awesome with cutoffs.
Dressy Shorts
They're still shorts, not a form-fitting silk pencil dress, so there's really no need to pay up for that teeny tiny bit of untailored fabric.
Denim Shorts
You can always find good ones for crazy-reasonable prices (and sometimes the best, most perfectly ripped ones are $2 thrift store finds), so why not?
Skimpy Tanning Bikini
You'll want your other swimsuits to be supportive and flattering and all that good stuff, but this one suit, the one you bought for the express purpose of tanning? It only needs to be strapless and teeny, so don't worry about anyting else and just find a cheap one.
White T-Shirts
They'll become your default on it's-too-hot-to-think days. Still, summer means sweat, and sweat means yellowing armpits (gross, but it happens to everyone) so buy a bunch of wallet-friendly ones in bulk.
Bright Clutches
You'll wear it with your white eyelet dress to a barbecue and your bright blue dress to a July wedding, but you probably won't want to wear it the other 8 months of the year, so don't splurge on it.
They make the best pool jewelry, and often the cheap-o versions look even cooler and more flea-market-find-y than their expensive counterparts. Take advantage of that.