How to Dress Like You’re Always on Vacation

This eye-catching shirt ($32, originally $65), patterned with delicate eyelets, is just the piece you need for relaxed vacation dressing. Pop it over a light, billowy dress or a pair of Bermuda shorts. Cinch the outfit with a belt and you'll have nailed a perfect out-of-office look that's still appropriate for work and play.

You don't need to be headed to the beach to don a straw hat. This wide-brimmed model ($25, originally $50) is breezy and elegant, perfect for lunch out with friends or happy hour with colleagues. It doesn't hurt that it'll protect you from the hot summer sun, too.

If "resort" is in the name, then you know the piece is for vacation. Such is the case with this casual-cool, preppy blouse ($27, originally $55), which comes in a slew of neutral and vibrant colors. Tuck it into a pair of chinos or jeans and pair it with a scarf for that French-girl feel (even if you're just headed to work).

Available in cream, a lovely lavender, and leafy green, this delightful button-down midi skirt ($45, originally $90) is both feminine and versatile. Tuck in a little cami and pop on an oversize cardigan and you'll feel ready for a walk on the beach, whether you're headed into the office or out for a day of errands.

Elastic waistbands are a staple for vacations, and we'd argue they should be a staple for everyday wear as well. These linen-blend pants ($35, originally $70), while relaxed and casual, are anything but schlumpy. Do a French tuck with a cute shirt, add a denim jacket, and a pair of sneakers, and you'll have achieved that coveted off-duty-model look.

This ethereal midi skirt ($45, originally $90) checks all the boxes of vacation dressing. It's made from super-soft cotton, it's airy and light, and it's as stylish as it is comfortable. The all-over shirring detail gives it some structure while still providing that fresh-from-the-beach look.

This bright, California poppy–colored shirt ($25, originally $50) just screams vacation and will make your skin glow, whether or not you've been spending days in the sun. We love the detailing on the embroidered sleeves, making it a warm-weather staple that's got some character.

When you're on vacation, you want outfits that are easy to throw on. No piece fits that description more than a jumpsuit ($55, originally $110). This black, wide-legged number can be dressed up or down, whether you pair it with a pair of sneakers for a day of commuting or espadrilles for a night out.