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.

  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 I have to wear a bra with resort wear?
  8. Resort style: Fit is key
  9. Chic resort outfits for women in midlife

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 to full-length evening dresses. 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 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, I wrote a 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.

How to accessorize resort fashion to look posh

Cross-body mini-bags 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 event.

Wood necklaces, bangles 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.

wooden sports watch http://www.woodwatches.com/#highlatitudestyle
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 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 Tweet

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

stylist in LBD with floral scarf

style blogger in black summer dress
Outfit II details: Unbranded layered summer dress, unbranded scarf, Madden Girl thongs, DIY necklace and bangle, Hermes collier de chien bangle (all own). 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 that they are relatively cheap. They become a bargain when you buy timeless and hence 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 I 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 make sure that you have the option 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.

mature woman in summer dress with straw hat and metal bag

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

Here are further summer resort outfit ideas.

White resort style designer dress with straw hat Alexander Wang dress with Paloma Picasso belt, Michael Kors sandals and straw hat (all own)
floral print resort dress Floral print patchwork sundress with suede espadrilles


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

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.

When you liked this post, please share it with your friends by tweeting them I just found some great resort style tips. #resortwear #agelessstyle Click To Tweet Thank you.

P.S. Are you registered for my weekly to biweekly newsletter that has additional information, and style theme collections? I’d highly appreciate it if you take the time to sign up and ask your friends to sign up too!!

Photos: G. Kramm

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