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
Start with a Capsule: Neutrals, Versatility & Smart Footwear
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.
Daytime
Quince Washable Silk Halter Top | J.Crew Slim Straight Jean | Oiled Leather Birkenstocks | Similar Alternative Birkenstocks | Mildred Raffia Belt | Mango Woven Straw Tote
This look is the perfect blend of laid-back luxury and effortless vacation style. The Quince Washable Silk Halter Top adds a touch of understated elegance, while the Slim Straight Jean from J.Crew keeps the silhouette classic and clean. Slip on Oiled Leather Birkenstocks for all-day comfort—or opt for a similar alternative—and finish the look with the Mildred Raffia Belt and a Woven Straw Tote for a beachy, textural twist. It’s the kind of outfit that works just as well for sightseeing as it does for a casual dinner al fresco.
Daytime
Madewell Denim Emmett Short | J.Crew Wren Slim Western Chambray Shirt | J.Crew Fine Rib Shelf Bra Tank Top | Similar Leather Belt | Alternative Buckle Sandals | Talbots Straw Foldover Clutch | Ray-Ban Aviator Gradient Sunglasses
This outfit strikes the perfect balance between casual and cool with a nod to classic Americana. The Madewell Denim Emmett Short and Wren Slim Western Chambray Shirt create a timeless denim-on-denim combo, layered over the Fine Rib Shelf Bra Tank Top for comfort and ease. A leather belt and buckle sandals add polished, practical touches, while the Talbots Straw Foldover Clutch (can be worn as a crossbody!) and Aviator Sunglasses complete the look with effortless vacation flair. Ideal for sightseeing, lunch in town, or wherever the day takes you.
Daytime
Talbots Wide Crop Linen Pants | J.Crew Garçon Shirt in Baird McNutt Irish Linen | White Tee | Veronica Beard Via Leather Flat Slide Sandals | Similar Woven Belt | Talbots Diamond Straw Tote | Havana Demi Bangles | Gold Tube Hoop Earrings | Similar Round Tortoise Sunglasses
Easy, breezy, and endlessly versatile, this look is all about relaxed sophistication. The Talbots Wide Crop Linen Pants paired with a crisp Garçon Shirt in Linen layered over a classic white tee create a light, breathable base that’s ideal for warm-weather travel. Leather Flat Slide Sandals and a woven belt add just the right amount of polish, while a woven tote brings texture and functionality.
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.
Lovely Linen
Linen Dress | Cashmere Sweater | Metallic Sandals | Rainbow Handbag | Pearl Toggle Necklace | Earrings
This look is the definition of elevated ease. A breezy Linen Dress offers effortless one-and-done styling, while a lightweight Cashmere Sweater draped over the shoulders adds a touch of chic layering for cooler evenings. Metallic Sandals bring a subtle shine, and a playful Rainbow Handbag adds a pop of color and personality.
Summertime Seersucker
Seersucker Shirtdress | Gold Thong Sandals | Diamond Straw Tote | Gold Hoop Earrings
Timeless and tailored, this Seersucker Shirtdress is a warm-weather classic that’s equal parts crisp and comfortable. Paired with Gold Thong Sandals, it’s the perfect blend of casual and chic. The Diamond Straw Tote adds texture and practicality, while Gold Hoop Earrings offer just the right amount of shine to keep the look effortlessly elevated. Ideal for brunch, sightseeing, or a relaxed afternoon out.
Elevated Linen
Strapless Linen Maxi Dress | White Linen Blazer | Gold Thong Sandals | Gold Choker | Two-Tone Stud Earrings | Bamboo Bracelet
Elegant yet relaxed, this look is made for warm evenings and coastal dinners. The Strapless Linen Maxi Dress brings graceful movement and breathability, while the White Linen Blazer adds a structured, polished layer. Paired with Gold Thong Sandals, it strikes the perfect balance between refined and easygoing. Finish the look with a Gold Choker, Two-Tone Stud Earrings, and a Bamboo Bracelet for a touch of earthy glamour.
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.
Linen Shorts
Black-and-White Zebra Print Suit | Straw Bucket Hat | Linen Drawstring Shorts | Gold Thongs
Bold and beach-ready, this Black-and-White Zebra Print Suit brings a touch of glam to poolside lounging. Paired with Linen Drawstring Shorts, it creates an effortless cover-up option that’s both breathable and chic. A Straw Bucket Hat adds sun protection with a playful twist, while Gold Thongs keep the look polished from the cabana to the café.
Extra Sun Protection
Long-sleeved Leopard Rash Guard | Matching Bottoms
Make a statement while staying sun-safe in this Long-sleeved Leopard Rash Guard with Matching Bottoms. The bold print adds a fierce twist to classic swimwear, while the full coverage offers both style and protection for active beach or pool days. It’s the perfect blend of fashion and function.
Oversized Linen Shirt
Tankini Top | Full-Coverage Bottoms | Linen White Button-Down | Straw Bucket Hat
This beach-ready ensemble is all about effortless layering. A Tankini Top paired with Full-Coverage Bottoms offers comfort and confidence, while a white linen button-down adds an airy layer that’s perfect for strolls along the shore or grabbing lunch poolside. Top it off with a Straw Bucket Hat for a stylish nod to sun safety.
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.
Athleisure Vacation Outfit Inspiration
Varley Callie Knit Top | Varley Highwaist Blue Shorts | Slip On Sneakers
Whether you’re heading to a yoga class or grabbing a smoothie after a morning walk, chic athleisure makes it easy to look polished and feel comfortable. The Varley Callie Knit Top paired with the Varley Highwaist Blue Shorts creates a stylish, coordinated set that’s perfect for active mornings. Add Slip-On Sneakers and a baseball cap to complete the relaxed, pulled-together look.
Lightweight Pajamas
Lands’ End Cooling 3-Piece Pajama Set | Lands’ End 2-Piece Cooling Pajama Set
When it comes to pajamas, pack a pair that helps you unwind in comfort and style. I love the Lands’ End Cooling 3-Piece Pajama Set for warm-weather getaways—lightweight, moisture-wicking, and polished enough to wear while enjoying your morning coffee on the patio.
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.
Elemis x Shrimps Travel Icon Collection
This limited-edition collab between Elemis and Shrimps is as pretty as it is practical. Inside the charming travel bag, you’ll find all the cult-classic skincare essentials—from the Pro-Collagen Cleansing Balm to their Marine Cream—perfectly sized for on-the-go glow.
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Coleen Rothschild Capsule Routine Starter Kit
If you’re new to Colleen Rothschild skincare, this capsule kit is the perfect introduction. It includes everything you need for a complete routine, from her Radiant Cleansing Balm to the must-have Sheer Renewal Cream—all in TSA-friendly sizes.
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Supergoop! Roundtrip Ready SPF Travel Kit
Don’t leave for vacation without this all-star SPF kit from Supergoop! It includes four of their best sun-protection formulas, so you can stay covered from head to toe—whether you’re sightseeing or soaking up poolside rays.
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Salt & Stone Body Care Essentials Kit
Clean, elevated, and beautifully unisex, this body care kit from Salt & Stone includes a luxe body wash, deodorant, and hand cream—just what you need to feel refreshed and polished wherever you land. The subtle scent is spa-worthy without being overpowering.
shop nowVacation 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.
Baggu Large Cosmetics Case
Roomy, wipeable, and adorably printed—this Baggu cosmetics case keeps all your toiletries organized with no fuss. The structured shape makes it easy to see everything at a glance, whether you’re in a hotel bathroom or on the go.
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Mini Jewelry Travel Case
This mini jewelry travel case is compact but cleverly designed with compartments for rings, earrings, and delicate chains. It’s a must-pack for keeping your accessories neat and ready to wear.
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Travel Steamer
Wrinkles don’t stand a chance. A compact travel steamer is a game-changer for keeping linen and cotton pieces crisp while on vacation. Lightweight and easy to pack, it’s one of those essentials you’ll wonder how you ever traveled without.
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Bagsmart Compression Packing Cubes
These compression packing cubes from Bagsmart are a lifesaver for maximizing space. They help keep your outfits organized by category or day and compress down to give you more room in your suitcase—yes, even for that extra pair of sandals.
shop nowClosing 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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