If San Juan, Punta Cana, or Cancún Is the Destination, These 11 Looks From Gap's Vacation Shop Are the Outfits
- Lace-Trim Maxi Dress
- Poplin Skirt Set
- Butter-Yellow Lace-Trim Set
- Gingham Linen-Blend Set
- Relaxed Trousers + Linen Shirt
- Pointelle Maxi Dress
- Linen-Blend Flare Trouser Set
- Lace-Trim Maxi Skirt Set
- Travel-Ready Hoodie Set
- Trouser Shorts + Sweater Over the Shoulder
- Drop-Waist Corset Dress
- Shop More Vacation-Ready Finds From Gap
I commute into Manhattan, and lately I've passed the time by checking flight prices to San Juan and Punta Cana. I'm so over these snow-covered sidewalks and the cold, gray landscape; I'm in desperate need of a sandy beach retreat. A tropical vacation is the perfect excuse for a shopping spree. I'll need cute matching sets, breezy linen trousers, elegant dresses, lace-trim skirts, and elevated basics. Good thing Gap just released its vacation shop. Find everything I mentioned and more. Spoiler: Cute matching sets are the secret to looking cute and packing smart. Below are 11 of the chicest and cutest Gap outfits to wear on your next getaway. Think butter-yellow sets, comfy travel wear, and beautiful dresses perfect for grabbing that sunset picture. Plus, I've included some chic sandals and accessories to go with.
While I hold out for the plane tickets to drop in price, here are the chic vacation picks and the Gap new arrivals I'm shopping. Scroll on to see the Cancún-ready vacation outfit ideas.
Lace-Trim Maxi Dress
Poplin Skirt Set
Butter-Yellow Lace-Trim Set
Gingham Linen-Blend Set
Relaxed Trousers + Linen Shirt
Pointelle Maxi Dress
Linen-Blend Flare Trouser Set
Lace-Trim Maxi Skirt Set
Travel-Ready Hoodie Set
Trouser Shorts + Sweater Over the Shoulder
Drop-Waist Corset Dress
Shop More Vacation-Ready Finds From Gap

Josephine Hadjiloucas is a New York–based writer. She first interned at Who What Wear UK in 2024 and later joined Who What Wear U.S. as an assistant shopping editor after graduating from the Fashion Institute of Technology in 2025. When she isn’t covering the latest Gen Z trends or updating her under-$100 Nordstrom wish list, you can find her browsing the racks of NYC’s best vintage stores or rewatching Moonstruck for the 50th time. “Snap out of it!”