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Coach bag, Nine West pumps, statement belt, Nordgreen watch, dress c/o Coolibar

Resort style or wear is also known as cruise style. It refers to season fashion for affluent customers – typically retired – who spend elongated times a resort in a warm climate region. This wear is growing in popularity. Over time it evolved from designer collections only for the weeks around Christmas/New Year to a year-round cross-cultural style.  This post introduces the key elements of resort wear, and provides tips how to style the look.


  1. Key Pieces of Resort Style
  2. Best Shoes to Wear with Resort Dresses
  3. How to Accessorize Resort Fashion to Look Posh?
  4. Sunglasses, Long Earrings, Necklace, Hair Down and a Hat Is Overkill
  5. Can You Wear Cheap Resort Wear over 50?
  6. Do You Have To Wear a Bra with Resort Wear?
  7. Resort Style: Fit Is Key
  8. Chic Resort Outfits for Women in Midlife
  9. Wrapping Up how to Best Wear Your Resort Style


Disclosure: There are affiliate links in this post.


Key Pieces of Resort Style

The wear encompasses everything from caftans, sandals, swimwear, walking shorts, cocktail dresses, maxi dresses to full-length evening dresses. Maxi dress outfits are favorites in summer. Shirts and kimonos often substitute for jackets (see featured outfit I). The garments are typically made from cotton, denim, microfiber, light linen, poplin, silk and straw. Accessories are often from natural materials like wood and glove-weight leather are favorites for jewelry. Large straw hats, sunglasses and open-toed shoes are further key elements.


stylist featuring an A-line style palm print dress
Example of resort style: Tropical print dress and sun hat c/o Coolibar, Nordgreen watch (Get 15% off with my discount code HLSTYLE), Hermes collier de chien bangle, Spring Step sandals, leave earrings



Resort clothing can be nautical-inspired, have classic Hawaiian, Tropical or Caribbean prints, bright floral prints, or ethnic prints like paisley or Calico prints. The wear conveys relaxation, but also the wearers affluence and appreciation of nature.


stylist wearing resort style with a green white stripe sunprotective dress, sunglasses, tan heels and striped fabric bag
Eagle Eyes sunglasses, Michael Kors tan sandals, Coach top handle bag, Judith Leiber gemstone necklace, Hermes collier de chien bangle , minimalist watch c/o Nordgreen and sun-protective midi dress c/o Coolibar


Resort clothes are lightweight, breathable, and low maintenance. Characteristic colors encompass hues typically associated with summer wear like mint, green, yellow, blue and whites. The waistline isn’t there (see featured outfit I, II), a 1920s inspired flapper-style low-waist, A-line style, or Empire-style.


over 50 years old woman in abstract print A-line resort outfit
Outfit I details: Liz Claiborne straw hat, BP espadrilles, Oliveo shirt, Hermes Medor watch, ethnic print sundress c/o Needham Lane, and sunglasses c/o glassesonline. This example has a clean modern cut and is made from high quality cotton with an ethnic inspired pattern (see the review of this dress).





Best Shoes to Wear with Resort Dresses

Resort dresses look great with metallic, embellished or simple leather thongs. Espadrilles are another great option. Flat gladiators in tan look great with ethnic print, stripe or chevron dresses. For petites Keds or Vans are cute too when the hem is around the knee and the dress has a floral or polka dot print.


fashion blogger in summer dress
Example of footwear. Outfit details: Apart dress, Hermes collier de chien belt, Anne Klein scarf, Chanel bag, and Madden Girl sandals



How to Accessorize Resort Fashion to Look Posh

Cross-body mini-bags or unique vegan designer bags for a look to envy in the vibe of the dress are great for an afternoon stroll or lunch. A straw, beats embellished, embroidered or fabric clutch is great for dinner. Stay away from anything too glam with the choice of your clutch. It’s a resort, not a party, even when there is a party. Exception: Formal events.


resort wear hat
Zoom-in on accessories


Wood necklaces, bangles, sunglasses and wooden watches are great accessories. Necklaces with colored beads work well with marine striped or solid resort dresses. Flattering sunglasses are a Must-have. See which sunglass frames are best for you.


wooden sports watch
Zoom-in on sports wooden watch c/o Jord


Sunglasses, Long Earrings, Necklace, Hair Down and a Hat Is Overkill

Your sunglasses and hat are part of your outfit. Long hair worn open with long dangling earrings, a necklace, sunglasses, and a hat are accessory overkill. Go for an up-do under the hat or a braided ponytail. Loose the necklace when you wear dangling earrings, a hat and sunglasses. Or go for studs, sunglasses, long necklace (to get away from the face), and a hat.

Stylist tip: Avoid that there is too much going on around your face.


back view of Hawaiian Apparel beach dress
Back view of resort dress c/o Hawaiian Tropic with interesting adjustment


Can You Wear Cheap Resort Wear over 50?

Yes and No. There is no straight answer. When wearing a resort dress in an inexpensive fabric, you need to up your resort outfit with with elevated quality accessories to achieve ageless style. Cheap accessories with a cheap dress look just cheap or even trashy.

Stylist tip: Mix inexpensive and more expensive items for great style.



layered black maxi dress with floral scarf golden sandals
This tank dress was a cheap thrift store find of a bridge designer.


style blogger in black summer dress
Outfit II details: Apart dress, unbranded scarf, Madden Girl thongs, DIY necklace and bangle, Hermes collier de chien bangle. The scarf was pinned to the dress to frame the back cleavage


A great thing about resort dresses is relatively low price. They become a bargain when you buy timeless, better quality pieces on sale after a season. Or buy a retro-style version, and accessorize it with contemporary pieces for a sophisticated modern look. Of course, always go for the highest quality you can afford. More on how you can save when shopping.



Do You Have to Wear a Bra with Resort Wear?

No matter which route you go, the main task when wearing resort clothes over 40 is to turn fashion into style. Always keep the option open to wear a bra underneath.


details of mesh-net dress
Zoom-in on the mesh dress to show details of the network with beads


blogger Nicole in a mesh dress over a slip dress
Outfit details: Mesh-net dress with silver colored pearls worn over a double layer sundress with Neo Tango shoes


Resort Style: Fit Is Key

A maxi dress should not sweep the ground (they have their own housekeepers), but end just above the ankles or below the knee. Avoid a front slit as it looks awkward when you sit at the bar. 😉 High-low hems and handkerchief hems are great options to show off your legs. A large silk scarf or shear cotton scarf make great cover-ups on chilly evenings.

Stylist tip: Show skin strategically because less skin is more stylish, and coverage protects your skin from aging.


Chic Resort Outfits for Women in Midlife

Stylist’s tip: Solid color resort dresses can easily change the vibe when you style them with different accessories.

Accessorizing with belts takes the dress up a notch. Or try to add scarves for style (see outfit II above and photo below).


influencer in maxi dress with straw hat and metal cross body designer bag
Back view of example outfit 3 described below to show the crawl details of the back cleavage


bold floral summer dress
Chica summer dress with straw hat, metal bag, and sandals (all own)


stylist in slip dress resort style
Floral print patchwork sundress with suede espadrilles, Hermes Constance bag, garnet statement necklace


fashion blogger over 50 in shirt worn over sundress
Wear a shirt as a cropped jacket by knotting it.



Resort Dress Code

You thought you were done with dress codes after your retirement! Maybe when you stay at home. But there are dress codes.

Formal resort attire means a cocktail party dress for women.

Resort elegant is a nice sundress for women.


Wrapping Up How to Best Wear Your Resort Style

Life and dressing stylishly doesn’t stop at retirement. On the contrary, fashion is more fun as it more comfortable. Note that there is a distinct different between resort style and the new Coastal Grandma Style trend.

Do you wish you had outfit tips like that for all kind of dressing situations in midlife? You can find the solution in my style recipe book How to dress for success in midlife. Buy it now.

Not yet retired or still going vacations? Then take a look at this guide for warm climate vacation style. There is namely a big difference in what you need for living in a resort and when being on vacation. No matter whether you are heading to a resort or going on vacation you may want to read about how to get into bikini shape fast.


Photos: G. Kramm

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