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This guide provides stylist’s tips for comfortable, effortlessly chic vacation outfits for various activities in warm climate regions. Read what to pack for best vacation style in warm climate regions.


  1. Best Vacation Style in Warm Climate Regions for Women over 40
  2. Vacation Style Does Not Mean Frumpy
  3. City Touring Style
    • Best Bags for City Tours
  4. Plan for the Weathers
    • On the Sunny Days, Protect Your Eyes
    • Rain Gear is Part of a Smart Vacation Wardrobe
    • Even When Vacationing in Hot Places Have a Jacket
  5. Pack with Outfits in Mind for Best Vacation Style in Warm Climate
    • Example Vacation Outfit Idea for Brunch
  6. What to Wear on the Travel to Your Vacation Destination?
  7. More Summer Vacation Outfit Ideas
  8. Vacation vs. Resort Style
  9. More on Summer Beach, Dance Cruise and Resort Vacation Style
  10. References


Updated: 5/15/2022

Disclosure: There are affiliate links in this post.


Best Vacation Style in Warm Climate Regions for Women over 40

Of course, what to wear on your summer vacation or your “winter” vacation in the Tropics depends on your plans and where you go. Most of us dream of white empty, endless beaches and sunshine from after breakfast to sunset.

Preferences for activities vary with lifestyle. When you live in a rural area, you may lust for sightseeing and visiting cities with their great cultural options, beautiful buildings, galleries, shopping malls, and museums. However, when living in a city, your dream may be to hike a National Park or climb Denali, America’s highest peak for a change of scenery. For Alaskans spending a vacation in Mexico or Hawaii is on the top of the list. Getting out of the heavy clothes into some flip-flops, wearing shorts and a cute top is their idea of best vacation style in warm climate. You get the idea.



over 50 years old woman in a summer dress with scarf
Outfit details: Ann Klein silk floral print scarf, Hermes collier de chien cuff, Apart slip dress, Hermes collier de chien belt, Madden girl sandals, headband, Hermes medor watch, and Chanel bag




Vacation Style Does Not Mean Frumpy

Go for comfortable casual items of high quality. You take a lot of photos and want to post them on social media, right? Therefore, clothes that are broken, faded, too loose, shrunk, too tight aren’t clothes to pack for a vacation trip. Even when your pack for aurora watching,  hiking, camping, or exploring the outdoors!

Vacation is your best time of the year, why wouldn’t you want to dress nicely for yourself?

Because there are so many different types of vacations that all require different gear, a one post fits all vacations will not do the trick. Therefore, let’s break it down and start with general information on warm region travel destinations and illustrate the general concepts by the example of a city touring outfit for warm countries. Then let’s turn to outfit inspirations for different activities in warm countries.


Stylist tip: Plan your wardrobe around a color combination of three.


stylist in beach maxi skirt for vacation
Side view maxi skirt


influencer in maxi skirt, Tshirt sweater
Sam Edelman crossbody bag, Eli Tahari pumps, Hermes collier de chien bangle, Nordgreen designer watch (Get 15% off with my discount code HLSTYLE), wooden sunglasses c/o Winkwood, sunprotective maxi skirt c/o Coolibar, T-shirt and sweater c/o Femme Luxe



City Touring Style

Comfortable shoes are a Must. When you are used to walk on heels, don’t make the mistake to go for flats when sightseeing. You will end up with sore calves. Instead go for some stylish comfortable wedge sandals or even stylish orthotic shoes (see the outfit inspirations at the end of the post).

Stylist tip: Never wear brand-new shoes when sightseeing or walking thru a museum or mall. New shoes may rub and you will end up with blisters that ruin your day and the next couple of days as well.

Tip: Blister alert! Never wear new shoes for a walk unless you want blisters on your blisters.


Best Bags for City Tours

Go for a cross-body bag, short shoulder or around town tote. They are much more stylish and safer than a backpack. It is in front of you or under your arm, i.e. all time under your watch. Furthermore, you won’t risk to topple over an entire exhibition by accident when turning around.

When you visit a city during the rain season have a stylish waterproof bag to protect your items.

summer outfit with floral skirt and hat
Loft Hawaiian print skirt, Jones New York top, Esprit shoulder bag, L.K. Bennet wedges, Festina watch, Liz Claiborne hat, Paloma Picasso glasses



Plan for the Weathers

Of course, you read the Wikipedia page section on the local climate of your destination. However, keep in mind that climate is the average weather over 30 years. On the contrary, your trip is reigned by the actual, real weather, not a statistical average (climate). Therefore, pack with the variability of the weather at the location in mind.

Even in the rain season, the Sun may come out once in a while, and in the dry season, you may have an intermediate wet week.


On Sunny Days, Protect Your Eyes and Skin

Being in the shade fails to rescue you from sunburn! Therefore, don’t forget sunglasses and a hat that go with the vibe of your outfits. Always put on sun cream as well even when it is cloudy or you walk on the shady side of the street.

You don’t want age spots and add wrinkles, do you?

For additional protection, you may opt to look for chic sun protective vacation wardrobe addition.


Even When Vacationing in Hot Places Have a Jacket

Just because your destination is in a warm climate region doesn’t guarantee warm weather all the time. Always pack a jacket. Not having one may ruin your vacation for as long as it takes to find a warm jacket that you want to buy and keep, and not just fix a current problem. Therefore, pack a cover-up (cardigan, denim or other light jacket) that you can throw over in chilly museums or when it gets chilly in the evening. When you don’t need the jacket outside, knot it around your waist or neck. It looks incredibly stylish and avoids losing it. Doing so also keeps your hands free to google the map on your phone to find your destination, take photographs with your iPhone, buy subway tickets, or just drink your iced coffee on your marsh to the next see-worthy place.

Tip: Knotting a jacket around your waist ups your style.


beach dress styled up for a promenade along the beach mall stores
Beach dress c/o Hawaiian Tropic Apparel, Chanel belt, Coach bag, and Dr. Scholl wedge sandals, Hermes enamel bangles, and Hermes collier de chien cuff. The dress is perfect for a stroll on the beach promenade



Rain Gear Is Part of a Smart Vacation Wardrobe

Rain is a natural event that even occurs on vacation. Off-season may mean more rainy days and cooler water than prime season.

Outfit for sightseeing on a rainy day
City touring look for a rainy day: Burberry trench coat, G-III skirt, August Silk top, Hunter rain boots, Jaeger tote and polka dot pocket umbrella


Plack an outfit for a rainy vacation day. A packable trench coat works for vacation and business travel alike. Of course, a foldable umbrella also does the trick. However, an umbrella has the disadvantage that you only have one free hand.


Pack with Outfits in Mind for Best Vacation Style in Warm Climate

When I pack for the best time of the year, I stick to one or two neutral colors and two bright colors that work great side by side. I pick items that maximize my options to wear, at minimum weight of the baggage. Read how to wear neutrals without looking boring.


over 50 years old woman in summer weekend look
Tissot watch, Rafaela striped T-shirt dress, Kieselstein Cord belt, Juicy Couture mules, Anne Klein floral print silk scarf, Longchamp Pliage bag, and Winkwood wood frame sunglasses


Example Vacation Outfit Idea for Brunch

The next look features a black, white and gray neutral desaturated color scheme as these colors look so posh together. The finishing touch is a basket bag. Petites need some lift when wearing a maxi dress. High heel or plateau sandals do the trick.

The look works because colors repeat several times in the look. For instance, black in the scarf, basket trim, layering top, and hat. White occurs in the drawstring of the dress, scarf, and basket trim. The different textures create interest.


style blogger over 50 in resort look with wrap gown, hat, and sunglasses
Sun hat, statement necklace with black rubber band, Jockey lace top, Kate Spade basket shoulder bag, quartz bangle, striped scarf, Musse & Cloud sandals c/o Coolway, mirrored sunglasses c/o Winkwood, and maxi wrap gown c/o Just Fashion Now. Do you recognize the place? When you are a regular reader, you may remember the post I wrote about Fairbanks new It place. In the evenings, a fire burns in the pit.


mildife woman sitting on a pit in a resort
Side view of summer vacation outfit to show details of the hat.


outfit details of vacation look in desaturated colors
Zoom-in on the vacation outfit to show details of the lace, wrap and basket. Black and white hut, quartz pendant with rubber band, Jockey lace camisole, Kate Spade basketg, quartz bangle, Hermes collier de chien cuff, striped scarf, white and wood sunglasses c/o Winkwood, and maxi drawstring dress c/o Just Fashion Now


What to Wear on the Travel to Your Vacation Destination?

For the travel to and from the destination cute joggers, a T-shirt, slides and a rain and wind protecting bomber are great options. They allow comfort in the plane and to adjust to the often chilly temperatures. Of course, a pair of comfy jeans, a Tee and the kimono do the trick too. Read more on comfy travel looks.


More Summer Vacation Outfit Ideas

Here are some visual inspiration for ageless  vacation looks over 40.

stylist wearing a warm climate vacation dress
Adriana Papel sun dress, BP espadrilles, and Paloma Picasso sun glasses, Hermes Constanze shoulderbag, Hermes collier de chien leather band, garnet necklace and bracelet


wrinkle free light weight dress perfect with cardigan for museum trips
Karina Dresses dress, Gucci bag, Moda International cardigan, Medor watch, and Musse & Cloud sandals c/o Coolway


mature blogger in casual city visiting outfit
Shein shirt, Orvis seersucker pants, Coach bag, statement belt, Winkwood sunglasses, and bomber jacket c/o Shein



Vacation vs. Resort Style

There is a distinct difference between resort and vacation style. In a resort, you stay for an extended time. Therefore, it is more like living at home, but with more entertainment opportunities than at home. Sightseeing is less an aspect in a resort than when you stay in a place for just 10 days. Also on vacation, you most likely don’t attend a formal affair. More on how to wear your resort style.


More on Beach, Dance Cruise, and Resort Vacation Outfits

This guide covered general aspects of vacation style in warm regions. More specific information on packing for a dance cruise, or what to pack for aurora watching in Alaska, and for a shortcut to a vacation wardrobe is available at the links. Finally, don’t forget that the pieces of your travel look should also go together with the pieces you packed in your baggage.

Did you know that you can find guidance for all kind of dressing situations in midlife, in my style book How to Dress for Success in Midlife? Buy it now.



Mölders, N., Kramm, G., 2014. Lectures in Meteorology, Springer, New York.

Photos: G. Kramm

© 2013-2022 Nicole Mölders | All rights reserved

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This Post Has 2 Comments

  1. Great advice! I always pack a light jacket and a pashmina because I often get cold in the evenings – even if it’s hot in the day. I have the same wicker bag from Zara that you’re wearing in the grey dress. Thanks for linking up!

    Emma xxx

  2. Love this, Nicole! Lots of great tips and beautiful outfits. I have to keep this in mind for my next trip – Angie,