Summer is the perfect time to refresh your wardrobe with whimsical pieces that strike up a conversation. Whether, for you, that means a next-level tank from K.ngsley with a keyhole cutout at the shoulder — an eye-catching detail that instantly elevates the entire look — or rather, collecting kitschy fruit-shaped bags from the likes of Kate Spade New York, our editor-curated shopping list aims to inspire street style outfits that are uplifting, trend-driven, and personal.

This season, we’re reaching for items that invite compliments while also browsing for basics that can be continuously re-worn: take Birkenstock’s new collaboration with Staud, for example, which offers a luxe, croc-effect update to its Arizona slide that’s been popular for years, or any of the sunglasses here that speak to totally unique tastes. From Ray-Ban’s retro gold-rimmed aviators to Rhude x Thierry’s sculptural, minimalist cat-eye and Elisa Johnson’s rectangular ’90s tortoise frame, these accessories are not easily retired. In the same vein, we’ve found a raffia beanie by NYC-based label Esenshel and a packable straw hat from Janessa Leoné that help to complete any swimwear moment you’ve got coming up (and also make for classic purchases).

Ahead, you can shop nap dresses, colorful tanks, a seashell-crocheted beach dress, flashy heels for happy hour, ultra-soft lounge shorts, and even a pair of panties in a watermelon color scheme. Let them usher in the summer months, and feel not a smidgen of guilt investing in a piece that’s functional, but also an optimistic addition to your closet.