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If you’ve ever packed for vacation and wished you had allowed more time to plan your outfit lineup — welcome to the club. Even as a shopping editor who has a pulse on the top fashion trends, I struggle to strategize my vacation outfits. This year, however, is going to be different as I’m honeymooning in Portugal for two weeks. I’m allowing ample time to shop, plan a lineup of incredibly chic outfits and pack for my European vacay.
Below, I rounded up everything I bought for easy packing — and it’s all going inside a carry-on suitcase and a small personal item! My list includes a comfy loungewear set for travel days, day-to-night dresses, functional handbags, beyond-comfortable walking shoes and clever luggage to keep everything organized. Whether you’re headed on a European vacation or you’re spending a week somewhere stateside, use my list below as inspiration for how to pack for vacation without sacrificing a chic outfit lineup.
Everything I’m Packing for My Portugal Vacation
Clothing
1. Airport ‘Fit: First things first: I’m packing this European-looking matching set for long travel days. The loose top and wide-leg pants make it feel like pajamas, yet I’ll still look dressed up enough for daytime activities once we land.
2. Timelessly Chic: Not only is a loose and airy blouse a smart pick for vacation — but it’s also versatile, instantly dressing up shorts, jeans or a skirt. Plus, it never feels drab or boring. It gives a timeless polish to anything you pair with it, which is a real win considering you can rely on this outfit combo time after time.
3. Everyday Winner: I’m a sucker for an athletic dress with built-in shorts. This tennis-style pick comes in over a dozen colors, and it easily beats wearing shorts and a tee. I plan on wearing this baby on days where we’re exploring the streets and beaches of Portugal for 6 hours straight.
4. Day-to-Night: There’s just something about a brown maxi dress with white polka dots that screams ‘winery day’ to me. And that’s exactly when I plan to wear this chic number as I explore Porto’s wine region.
5. Flattering Sundress: There’s no such thing as packing too many dresses for vacation. In fact, it’s the smartest outfit you can pack — especially when it’s this 100% cotton navy gingham dress. Wear it with sneakers for exploring the city, then switch into wedges for dinner.
6. Not Jean Shorts: For summer 2026, jean shorts are out, and loose, elastic-waist styles are in. I’m packing these chambray shorts from Quince to pair with blouses, sweaters and casual tees. Plus, they’re not restricting, meaning you can comfortably walk 10,000+ steps in Europe without constantly tugging and pulling them down.
7. Double Duty: Not only do these loose, linen-blend pants nail chic coastal style, they also pull double duty as a day pant and swimsuit coverup. For daytime outings, I’ll style them with a one-piece swimsuit and sandals. For the evening, I’ll dress them up with a loose tank and wedges.
8. Florals, Please: When you’re beach hopping and quite literally spending all day in the same clothes, a one-piece swimsuit is the way to go. This flattering number is adorned with pink and orange flowers, giving it a coastal feel. Throwing on flowy pants instantly makes it read polished, not pool deck (which is perfect for spontaneous lunch plans!).
Shoes
9. True Slip-ons: Hands down, the only 100% slip-on shoe I’ve ever tried are Kizik sneakers. The patented hands-free heel is specifically designed to be more flexible, allowing you to gently slip them on without using your hands. I can’t recommend them enough for logging miles on vacation and breezing through TSA.
10. Celeb-Approved: The one and only Katie Holmes wears Vivaia Mary Janes, and it’s easy to see why. Lightweight and comfortable, the dainty shoe is equal parts chic and functional. Wear them with a sundress or sandals; the choice is yours!
11. Walking Sandals: Few (and I mean few) sandals are designed for long days of walking, but Vivaia walker sandals get the job done. The arch support technology and cushioned insole cradle feet in comfort, which is especially important on European vacations where you’re stuck in the same shoes for 10+ hours.
Bags & Accessories
12. Clever Compartments: When it comes to picking a personal item, always, always look for a bag with sneaky shoe storage, like the Luka Duffle from Calpak. I can fit two pairs of shoes into the bottom compartment, and there’s still enough room in the main compartment for a book or tablet, snacks, toiletries — you name it.
13. Chic Crossbody: Full transparency, I picked this canvas crossbody entirely for its chic appearance (I mean, doesn’t it just scream ‘European vacation’?!). Secure zipper compartments and a magnetic closure keep cards, lip balm, and my phone secure and organized. It’s not a true anti-theft bag, so it’s not what the pros will recommend traveling with — but it’s cute and convenient nonetheless.
14. Packable Sunhat: A scalp burn on vacation is the absolute worst, so I’m packing this foldable sunhat with UV protection. It’s way more chic than your average baseball cap!
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