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Michael Kors tan heels, Eagle Eyes sunglasses Coach striped bag (all own) and sunprotective resort dress c/o Coolibar

Retirees who can affort it spend the winters in resorts. This post explains resort style and how to best wear your resort style.


  1. What Is Resort Style?
  2. Key Pieces of Resort Style
  3. Best Shoes to Wear with Resort Dresses
  4. How to Accessorize Resort Fashion to Look Posh?
  5. Sunglasses, Long Earrings, Necklace, Hair Down and a Hat Is Overkill
  6. Can You Wear Cheap Resort Wear over 50?
  7. Do You Have To Wear a Bra with Resort Wear?
  8. Resort Style: Fit Is Key
  9. Chic Resort Outfits for Women in Midlife
  10. Wrapping Up how to Best Wear Your Resort Style
  11. Top of the World Style Linkup No. 316

Disclosure: There are affiliate links in this post.

What Is Resort Style?

Resort style or wear is also known as cruise style. It refers to season fashion for affluent customers – typically retired – who spend the cold months in a winter 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. Themes of collections can be nautical-inspired, classic Hawaiian prints, Caribbean prints, bright floral prints, paisley or block print Indian inspired prints. The wear conveys relaxation, but also the wearers affluence and appreciation of nature. This post introduces the key elements of resort wear and provides tips how to style the look.


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 sunprotective midi dress c/o Coolibar


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.

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, or Empire-style.

The dress in the example photos below is from very nice, high quality cotton. Its clean modern cut is paired with a nice ethnic abstract Indian block print inspired pattern. In case you missed it, read the review about the dress.


resort wear hat

fashion blogger over 50 in shirt worn over sundress

stylist in sundress with shirt as coverup

over 50 years old woman in abstract print A-line resort outfit
Outfit 1 details: Liz Claiborne straw hat with flower, BP espadrilles, Oliveo plaid cotton button-down shirt, Hermes Medor watch (all own), abstract ethnic print inspired A-line sundress c/o Needham Lane and sunglasses c/o glassesonline


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
Front view of example with ruffled sandals


style influencer in black slip dress with gold sandals
Apart slip dress, Hermes collier de chien belt, Anne Klein silk scarf, Chanel bag, and Madden Girl gold ruffle 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 the afternoon stroll and lunch. Have a straw, beats embellished, embroidered or fabric clutch 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.

Wood necklaces, bangles, sunglasses and wooden watches are great accessories. Necklaces with colored beads look great with marine striped or solid resort dresses. Go either for long earrings or sunglasses when wearing your hair down and a hat. All three in one outfit would be overload. More on which sunglass frames are best for you in this guide.


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


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

Don’t forget that your sunglasses and hat are part of the 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 and 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. In other words, avoid that there is too much going on around your face. You don’t want to hide, do you? 😉 And you don’t want to be mistaken for the Christmas tree.


back view of Hawaiian Apparel beach dress
Back view of resort dress c/o Hawaiian Tropic to show the hem, adjustment, and straight cut


Can You Wear Cheap Resort Wear over 50?

Yes and No. There is no straight answer. When you go for a resort dress in an inexpensive fabric, you need to up your resort outfit with with elevated quality accessories to achieve ageless style. Adding cheap accessories to a cheap dress ruins your look and make the entire outfit look just cheap or even trashy. Looking cheap is not the style you want ever.

Tip: Mix inexpensive and more expensive items for great style. #agelessstyle Click To Tweet

The tank dress in the featured outfit II was a cheap thrift store find of a bridge designer.

layered black maxi dress with floral scarf golden sandals

Resort style accessorizing

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 in such a way that it frames the back cleavage


A great thing to like 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.


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.

mesh dress for going out in a resort
Layering a layered dress with mesh dress


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 of the 2nd example: 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. Don’t go for a front slit as it looks awkward when you sit at the bar. 😉 High-low hems are great options too as are handkerchief hems to show off your legs. A large silk scarf or shear cotton scarf make great cover-ups when it gets a bit chilly in the evening. As always stay to showing skin strategically. Keep in mind, less skin is more stylish. Moreover, coverage protects your skin from aging.

Show skin strategically even at the resort for great style. #agelessstyle #resortstyle Click To Tweet


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.

A statement leather belt takes the dress up a notch or try to add scarves for style. See for instance Outfit II in this post. More on best accessorizing with belts in this guide.

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


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.

When you are on a fashion budget see this post on how you can save when shopping. An alternative is to go second hand.

Not yet retired and still doing 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.



Top of the World Style Linkup No. 316

Top of the World Style linkup logo

Welcome to the Top of the World Style linkup party.


Jacqui of Mumma B Stylish in jeans, loafers, floral top and midi length cardigan became Top of the World Style Winner
Jacqui from Mumma B Stylish became the Top of the World Style Winner. Photo from her post


Penny Kocher is floral leggings and pink top
Penny Kocher from Frugal Fashion Shopper became the Top of the World OOTD Readers Fav. Photo from her post


Leelo of Beauty by Miss L in paisley maxidress
Leelo from Beauty by Miss L became Top of the World OOTD My Fav. Photo from her post


Congrats Ladies! Grab your award buttons.

Please invite your friends.
Come join me at the Top of the World Style #linkup party. #ffblogger Click To Tweet

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Photos: G. Kramm

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