The 11 Best Gap Vacation Outfits 2026


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

Cute Vacation Outfits from Gap 2026

Poplin Skirt Set

Cute Vacation Outfits from Gap 2026

Butter-Yellow Lace-Trim Set

Cute Vacation Outfits from Gap 2026

Gingham Linen-Blend Set

Cute Vacation Outfits from Gap 2026

Relaxed Trousers + Linen Shirt

Cute Vacation Outfits from Gap 2026

Pointelle Maxi Dress

Cute Vacation Outfits from Gap 2026

Linen-Blend Flare Trouser Set

Cute Vacation Outfits from Gap 2026

Lace-Trim Maxi Skirt Set

Cute Vacation Outfits from Gap 2026

Travel-Ready Hoodie Set

Cute Vacation Outfits from Gap 2026

Trouser Shorts + Sweater Over the Shoulder

Cute Vacation Outfits from Gap 2026

Drop-Waist Corset Dress

Cute Vacation Outfits from Gap 2026

Shop More Vacation-Ready Finds From Gap

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