Vacation is the perfect time to press pause on the daily grind and indulge in relaxation, exploration, and style. Whether you’re headed to a beachside resort, European city, or wine country getaway, packing with purpose makes all the difference. Today, I’m sharing curated vacation outfit inspiration for women over 50 that takes the guesswork out of what to wear—so you can feel chic, comfortable, and ready for every adventure.
Vacation Outfit Inspiration
When it comes to packing, I swear by a neutral capsule wardrobe. Stick to a color palette that works together—think ivory, camel, black, navy, and olive. This allows you to mix and match effortlessly without overpacking. Denim and linen are vacation staples for a reason—they mix and match effortlessly with other pieces and hold up well during travel. Linen keeps you cool and polished in warmer climates, while lightweight denim offers structure and versatility without wrinkling easily. Layer lightweight pieces that work in different climates and settings, from a museum tour to an al fresco dinner.
Shoes can make or break your travel style. Pack one casual walking shoe, one elevated sandal, and a poolside slide—and plan outfits that can flex depending on your itinerary.
Tour-Ready, Fashion-Forward
Sightseeing calls for comfort without sacrificing polish. I love a pair of lightweight white denim or relaxed linen pants paired with a breathable top. Add a wide-brim hat, a crossbody bag or tote, and supportive sneakers or sandals, and you’re ready to go from the local market to a city walking tour.
All-Day Style, No Outfit Change Needed
Some days blur the line between daytime exploring and casual evening dining. A breezy midi dress with comfortable espadrilles can transition beautifully. Just swap out your accessories: think a woven tote by day and a clutch with layered necklaces by night.
Shop Vacation Outfit Inspiration
Cross-Dyed Linen Shirtdress | Suede Espadrilles | Marais Stretch Belt | Suede Shoulder Bag | Gold Hoop Earrings | Alternative Statement Necklace | Caviar Bangle | Caviar Watchband
Casual Glam for Vacation Nights
For dinner at that charming little bistro or a seaside restaurant, opt for easy elegance. A maxi dress in a rich tone or a flowy blouse with tailored trousers creates an elevated, relaxed look. Add block heel sandals, a statement earring, and a pop of color with your accessories for instant vacation glam.
Low-Key Luxe for Pool & Beach Days
Cover-ups can double as lunch attire when chosen wisely. I always pack a long button-down shirt, a classic one-piece swimsuit, and a wide-brimmed straw hat. Raffia slides or flip-flops complete the look. Don’t forget oversized sunnies and a beach tote that fits everything.
Chic Comfort for Every Leg of the Journey
Comfort is key for travel days, but that doesn’t mean sacrificing style. A soft matching set in a breathable knit or a wide-leg lounge pant with a tank and cardigan makes the perfect travel look. Bonus: it transitions seamlessly into loungewear once you arrive.
Style on the Move
Aspen Travel Set | Similar Raffia Slide Sandal | Packable Panama Hat | Similar Gold Hoops | Alternative Statement Necklace | Delsey Suitcase
If you’re flying, swap the sandals for chic, lightweight slip-on sneakers, like the Rothy’s Original Slip-On Sneaker
Whether I’m easing into the day or wrapping it up, I reach for loungewear that feels just as good as it looks. Travel sets from Frank & Eileen prove that comfort and style can go hand in hand — no effort required. Soft, cozy, and endlessly wearable. Perfect for early mornings, travel days, or slow afternoons. Just add slip-on sneakers or a slide, and you’re instantly pulled together. One of my favorites is the Aspen Travel Set is a long-sleeved top and cropped pants. But Frank & Eileen have so many options to suit your travel plans. Try the Hamptons Travel Set for stylish shorts and an elegant, drapey cape-like top.
Vacation Outfit Inspiration: Toiletry Essentials
Keep it simple and streamlined with travel-sized skincare, SPF, and a tinted moisturizer with built-in SPF. Don’t forget hydrating lip balm and facial mist to refresh after a long flight. I always bring a packable cosmetic bag with separate compartments to stay organized.
Vacation Outfit Inspiration: Packing Essentials
Packing cubes are a game-changer—group outfits by category or day. A small steamer, travel laundry bag, and compact jewelry case help you stay polished on the go. And if you’re checking a bag, tuck a change of clothes and basic toiletries in your carry-on—just in case.
Closing Thoughts
Vacation Outfit Inspiration for Women Over 50
Packing smart lets you enjoy your vacation without fussing over outfits. With this guide, you’re ready to build a functional, fabulous travel wardrobe. Whether you’re lounging poolside, sightseeing, or heading out for dinner, you’ll feel confident and stylish every step of the way. Wherever you’re headed next, may it be filled with sunshine, great memories, and effortless style.
For more Travel inspiration, tips, and tricks for making the most of your getaway, check out the Travel Section on Style at a Certain Age.
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