Vacation style doesn’t have an age limit, especially when you’re aiming for that luxurious resort feel! I’ve spent decades helping mature fashionistas pack for paradise, and let me tell you—comfort and elegance can absolutely go hand-in-hand. Let’s explore 19 resort outfit ideas that’ll have you feeling fabulous, sophisticated, and vacation-ready, no matter your age.
1. Flowy Maxi Dress with Wide-Brimmed Hat
Ah, the ultimate resort classic! A lightweight, ankle-grazing maxi in breathable cotton or linen creates instant elegance without trying too hard.
Pair with a dramatic wide-brimmed hat and suddenly you’re not just a tourist—you’re a mysterious fashion icon gliding through the lobby. The forgiving silhouette flatters every figure.
2. Linen Palazzo Pants and Silk Blouse Combo
Where comfort meets sophistication! Those billowing palazzo pants provide movement while disguising any lower-body concerns we might fret about.
Top with a simple silk blouse—tucked in loosely at the front—and you’ve mastered that effortless chic that younger women spend hours trying to achieve. Your experience shows in your style choices!
3. Caftan Cover-Up with Statement Jewelry
Darling, nothing says ‘I’m vacationing in style’ quite like a vibrant caftan! This one-and-done piece transitions beautifully from poolside to dinner.
Throw on a chunky turquoise necklace or oversized gold earrings, and you’ve elevated the entire look. Remember when these first became popular in the 70s? We’re bringing them back with panache!
4. Cropped Linen Trousers with Striped Boat-Neck Top
How I adore this nautical-inspired pairing! Crisp white cropped trousers hit at that sweet spot above the ankle—so much more flattering than full-length in the heat.
Match with a navy-and-white striped top, and suddenly you’re channeling Riviera chic. A red lip completes this timeless ensemble that never goes out of style.
5. Tailored Bermuda Shorts with Lightweight Blazer
Though many shy away from shorts after a certain age, properly tailored Bermudas hitting just above the knee are absolutely ageless! I’ve paired mine with a lightweight linen blazer countless times.
This combination works wonderfully for resort dinners with a dress code. The structure provides polish while keeping you cool in balmy evening breezes.
6. Wrap Dress in Tropical Print
Whoever invented the wrap dress deserves eternal gratitude! This miracle garment defines the waist while skimming everything else. When rendered in a vibrant tropical print, it screams ‘vacation mode activated!’
Hence my advice to pack at least two variations. The V-neckline elongates the neck while the adjustable tie ensures perfect fit regardless of vacation indulgences.
7. Dressy White Capris with Tunic Top
White capris might sound intimidating, but in a quality fabric with proper fit, they’re remarkably flattering! I’ve converted countless clients to this resort staple.
Paired with a longer tunic top in a jewel tone, the effect is slimming and sophisticated. Add metallic sandals and you’re ready for anything from gallery browsing to sunset cocktails.
8. Loose Linen Shirt Over Cotton Tank with Drawstring Pants
However hot the destination, this trio keeps you cool while looking collected. The oversized linen shirt (worn open) creates a vertical line that lengthens your silhouette.
The tank provides necessary coverage, while those drawstring pants offer adjustable comfort. I call this my ‘market day ensemble’—perfect for shopping local crafts without sacrificing an ounce of style.
9. Patterned Midi Skirt with Simple T-Shirt
Youth may have skinny jeans, but we have the midi skirt—our secret weapon! A swishy A-line in a gorgeous print brings movement and joy to your resort wardrobe.
Though it seems counterintuitive, pairing with a fitted tee creates perfect proportion balance. This outfit works for breakfast, sightseeing, and even casual dinners with just a change of accessories.
10. Lightweight Jumpsuit with Statement Belt
Before you dismiss jumpsuits as too youthful, hear me out! A well-cut version in a solid color creates a streamlined silhouette that’s incredibly flattering. The secret? Adding a statement belt to define the waist.
Choose one with wider legs for ease of movement and bathroom visits (let’s be practical, darlings!). This one-piece wonder packs beautifully without wrinkling.
11. Dressy Capri Set with Matching Jacket
Matching sets have made a triumphant comeback, and I couldn’t be happier! For resort evenings, a capri pant with coordinating top and light jacket offers sophistication with comfort.
Though younger generations might call this “grandma style,” we know better—it’s timeless elegance! Choose tropical-weight fabrics in soft pastels or bold jewel tones depending on your coloring.
12. Crisp Button-Down Shirt with White Jeans
Never underestimate the power of a perfectly fitted button-down! In breathable cotton or linen, it’s my go-to for those “what should I wear?” moments at resorts.
White jeans (straight or slightly bootcut) complete this classic pairing that works from St. Tropez to Santorini. Roll the sleeves, add oversized sunglasses, and you’re channeling timeless movie star energy.
13. Tiered Sundress with Espadrille Wedges
If your knees remain one of your best features (lucky you!), a tiered sundress hitting just below the knee offers breezy sophistication. The graduated tiers create movement while disguising any midsection concerns.
Where comfort meets height? Espadrille wedges! They provide stability without sacrificing style, making them ideal for navigating those cobblestone resort pathways.
14. Silk Printed Kimono Over Basic Tank and Pants
My personal packing secret? A statement kimono transforms basic pieces into resort-worthy outfits! Draped over a simple tank and slim pants, this third piece adds drama and elegance.
Though lightweight, silk kimonos provide just enough arm coverage for those of us who prefer it. The flowing silhouette creates beautiful movement—perfect for making an entrance at the resort restaurant.
15. Wide-Leg Cropped Pants with Off-Shoulder Top
Contrary to outdated fashion rules, women over sixty can absolutely rock an off-shoulder top! When paired with sophisticated wide-leg cropped pants, the balance is perfect.
Your shoulders age remarkably well compared to other areas, so why not showcase them? This combination feels fresh yet appropriate for resort dinners. A hint of décolletage is eternally chic!
16. Embroidered Tunic with White Slim Pants
Nothing says ‘resort luxury’ quite like intricate embroidery! A tunic with beautiful needlework around the neckline instantly elevates your vacation wardrobe.
While younger women might pair this with shorts, we know the secret—slim white pants provide more flattering coverage without sacrificing style. This combination transitions seamlessly from day excursions to evening drinks.
17. Dressy Resort Shorts with Matching Blazer
Yes, shorts can be sophisticated! Longer, tailored versions in a luxurious fabric paired with a matching blazer create a resort-appropriate suit alternative.
Though unconventional, this pairing offers incredible comfort in hot climates while maintaining polish. The matching set creates a column of color that elongates your silhouette. I’ve converted many skeptical clients to this look!
18. Sleeveless Shirtdress with Straw Accessories
If there’s one dress style universally flattering for mature women, it’s the structured shirtdress! The button-front design creates a lengthening vertical line while the collar frames your face beautifully.
However hot the destination, this classic remains polished. Add a woven belt and coordinating straw bag for that cohesive resort look that appears effortlessly put-together.
19. Relaxed Linen Set with Statement Necklace
Linen separates in matching colors create instant resort sophistication with zero effort required! The relaxed fit handles humidity gracefully while maintaining an air of intentional style.
Though wrinkles are inevitable with linen, they’re part of its charm. Add a bold artisanal necklace purchased from your destination for a personal touch that elevates the entire ensemble.