Retirees who can affort it spend the winters in resorts. This post explains resort style and how to best wear your resort style.
- What Is Resort Style?
- Key Pieces of Resort Style
- Best Shoes to Wear with Resort Dresses
- How to Accessorize Resort Fashion to Look Posh?
- Sunglasses, Long Earrings, Necklace, Hair Down and a Hat Is Overkill
- Can You Wear Cheap Resort Wear over 50?
- Do You Have To Wear a Bra with Resort Wear?
- Resort Style: Fit Is Key
- Chic Resort Outfits for Women in Midlife
- Wrapping Up how to Best Wear Your Resort Style
- 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.

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.

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.


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.

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.

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 TweetThe tank dress in the featured outfit II was a cheap thrift store find of a bridge designer.
Resort style accessorizing

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.



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.



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
Welcome to the Top of the World Style linkup party.



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
Photos: G. Kramm
© 2013-2022 Nicole Mölders | All rights reserved