How to wear vacation style (warm climate)
How I wear my vacation style

Best vacation style 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. At least when you live in the Westerlies with low pressure systems dumping rain every 3 to 5 days or so. 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. When you live in a city, your dream may be to hike a National Park or climb Denali, America’s highest peak for a change of scenery. When you live in Alaska, spending vacation in Mexico or Hawaii is on the top of the list. Getting out of the heavy clothes into some flip-flops, shorts and a cute top – vacation style. You get the idea. 😉 This guide provides stylists tips for comfortable, effortlessly chic summer vacation outfits for various activities in warm places.

  1. Best vacation style 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
    • Off-season may mean more rainy days
    • Rain gear is part of a smart vacation wardrobe
  5. Summer vacation outfit ideas
  6. Even when vacationing in hot places have a jacket
  7. Summer vacation outfit ideas
  8. More on summer beach, dance cruise and resort vacation

Disclosure: There are affiliate links in this post.

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? Thus, 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?

Since 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. Furthermore, various outfit inspirations for different activities in warm countries are given later in this post.

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. That’s why I wear rubber boots with heels in the outfit above. Instead go for some stylish comfortable wedge sandals or even stylish orthopedic shoes like the ones shown in the outfit inspirations below.

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.

Blister alert! Never wear new shoes for a walk unless you want blisters on your blisters. #vacation #shoelover Click To Tweet Never wear new shoes for sightseeing unless you want blisters on your blisters. #sightseeing Click To Tweet

Best bags for city tours

Go for a cross-body bag or short shoulder bag. They are much more stylish and safer than a rucksack. It is 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. 😉

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. Your trip, however, is reigned by the actual 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.

bad weather on vacation outfit

Rain outfit for a city touring with trench coat, rubber boots and umbrella

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

On the sunny days, protect your eyes

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. The sunbeams get reflected everywhere in a city, on windows, on water, even on concrete. Thus, there is enough diffuse sunlight that can cause a sunburn. You don’t want age spots and add wrinkles, do you?

Off-season may mean more rainy days

Warning: Never take a vacation with me. It is a guarantee to have rain. I once took a vacation in Morocco to tour the King’s cities and the Sahara desert. They hadn’t had rain in three years. Guess what? The plane landed and it purred. 🙁

Another example was 1992. There were awful wildfires in California. My parents were at their retirement home in Dirkshorn, The Netherlands where they had no phone (on purpose). Thus, I wrote them a card saying that we would fly to California to extinguish the fires. My husband and I were just married and he said “Why are you writing such garbage to your parents? You didn’t take a job as a firefighter!” “You’ll see” I just responded. We landed in San Diego and it started to rain. 🙂

Rain gear is part of a smart vacation wardrobe

I really like my packable Burberry trench coat for vacation and business travel alike. It is very light and folds very small so I can have it handy in my bag all the time. Of course, a foldable umbrella also does the trick. However, it has the disadvantage that you don’t have both hands free anymore.

Even when vacationing in hot places have a jacket

Just because your destination is in a warm climate region doesn’t mean that you have warm weather all the time. Always pack a jacket. Not having one may ruin your vacation for as long as it takes you to find a warm jacket that you want to buy and keep, and not just fix a current problem. Thus, don’t forget 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. This way, you won’t risk losing it and keep your hands free to google the map on your phone to find your destination, take pictures, buy subway tickets, or just drink your iced coffee on your marsh to the next see-worthy place. In addition, the knotted jacket ups your style.

Knotting a jacket around your waist ups your style. #styletip #agelessstyle Click To Tweet

Summer vacation outfit ideas

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

over 50 years old fashion blogger in red-white-blue casual outfit The Limited polo shirt with London Jean boyfriend jeans, Keds, Constance bag, Kieselstein Cord belt and buckle, and sunglasses c/o ShopGlasses
style blogger in sightseeing outfit for a rainy day T-shirt c/o Marine Layer with own Burberry Brit trench coat, Longchamp bag, London Jean boyfriend jeans, and Hunter rain bootsNicole in casual vacation outfit with pants and a button-down shirt J. Crew seesucker pants with Oliveo linen shirt, Dr. Scholl wedge sandals, Kieselstein Cord belt, H buckle, Kate Moss for Longchamp bag (all own), and wooden watch c/o Jord
mature style blogger donning a resort sundress Sun dress with espadrilles and Paloma Picasso sun glasses (all own)
mature woman in maxi summer dress Chica maxi dress, Collier de Chien belt, metal bag, straw hat, statement necklace, and Juicy Couture slides (all own)
wrinkle free light weight dress perfect with cardigan for museum trips Karina dress, Gucci bag, Moda International cardigan, medor watch (all own), and wood Musse & Cloud sandals c/o Coolway
mature blogger in casual city visiting outfit Shein shirt, Orvis summer pants, Coach bag, statement belt (all own), sunglasses c/o Winkwood and bomber c/o Shein
printed resort dress with blouse as jacket Samantha Olsen dress c/o HSN with own Salvatore Ferragamo pumps, Notations silk blouse worn as jacket, and Ray Ban sunglasses
Olivia and Joy outfit for city touring City touring look: Spring bag c/o Olivia + Joy worn with own Anne Klein sweater, BCBG capris, Vigotti shoes, Jones New York cardigan, and pearl necklace
Vionic Shoes orthotics for comfortable walks along the beach mall Ariana wedge slides c/o Vionic Shoes with own Liz Claiborne sweater, BCBG capri, Burberry bag, and Moda International cardigan
blogger in sightseeing look for rainy days Double HH boots, Oliveo denim skirt, Kieselstein Cord belt, college T-shirt, silk scarf and HH men’s raincoat (all own)
city touring casual outfit Casual sightseeing look with Moda International cardigan knotted at the waist, London BF, Longchamp pliage, Nicole sandals, Brooks Brothers sweater, Ray Ban sunglasses, and Festina watch (all own)
fashion book author in denim dress Liz Claiborne denim dress, statement belt, Tommy Hilfiger wedge sandals, Coach bag, Festina watch (all own), and wooden pineapple earrings c/o Green Tree Jewelry
lifestyle blogger landing after jumping off a huge stone in a knit dress with purse and Keds Zaful knit dress, leggings,Keds, Notations white and black striped cardigan, Hermes shoulder purse, and statement necklace (all own)

Please feel free to pin the photos to your pinterest post.

Pack with outfits in mind

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. See this shortcut to pack a vacation wardrobe.

More on beach, dance cruise and resort vacation outfits

This guide covered general aspects of vacation style in warm regions. You can find more information on what to pack for a dance cruise in the post at the link. Interested in heading out to the beach and wonder about short summer vacation outfits? Don’t forget to think about a joyful, chic vacation travel look which pieces should also go together with your other pieces.

Note there is a distinct difference between resort and vacation style. In a resort, you stay for an extended time. Thus, it is more like living at home, but with more entertainment opportunities than at home. Sightseeing is less an aspect than when you stay in a place for just 10 days on vacation. Also on vacation you most likely don’t attend a formal affair. You can read more on how to wear resort style in the post at the link.

When you loved this post and want more of this type of tips, for all kind of dressing situations in midlife, my style book How to Dress for Success in Midlife will keep you covered. It has a load full of styling tips you don’t want to miss. Buy it now.

Have you planned your summer or warm region winter vacation already? Where will you go? What will you pack? Have you already bought some new resort dresses? How do you style them? Just curious.

When you liked this post you may want to get further inspirations on sightseeing looks and/or read what to pack for a vacation in Alaska.

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I just found some great vacation style tips. #vacationstyle #travel Click To Tweet Thanks.

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Photos: G. Kramm

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