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 1) the key elements of resort wear including what is considered resort style, 2) provides tips how to style the look with photos of resort style outfit ideas, and answers the questions “How should I dress for a resort?”, as well as.
- What Are the 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?
- How to Wear Resort Clothes?
- Chic Resort Wear Outfit Ideas for Women in Midlife
- Resort Dress Code: What Is Resort Formal and Resort Elegant?
- Wrapping Up how to Best Wear Your Resort Style
Disclosure: There are affiliate links in this post.

What Are The Key Pieces of Resort Style?
Key elements of resort wear encompass 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 recently also hemp fabrics.
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 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.
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.

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, the dress has a floral or polka dot print or you wear separates in a balanced way.
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.

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

Can You Wear Cheap Resort Wear over 50?
Yes and No. There is no straight answer regarding to resort looks for women in midlife. However, you can use this rule of thumb: 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.
Tip: Mix inexpensive and more expensive items for great style.

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 to 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 when you are allergic to adhesive bras.

How to Wear Resort Clothes?
Fit is important. A maxi dress, for instance, 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.
Tip: Show skin strategically because less skin is more stylish, and coverage protects your skin from aging.
Chic Resort Wear Outfit Ideas for Women in Midlife
Tip: Solid color or striped resort dresses can easily change the vibe when you style them with different accessories.
Accessorizing with belts takes a dress up a notch. Or try to add scarves for style (see featured look, outfit II above).



Resort Dress Code: What Is Resort Formal and Resort Elegant?
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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Very well written
Thanks for sharing