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Jones New York Hawaiian shirt, pink skater skirt, Michael Kors leopard print satchel, Ivanka Trump cap-toe pumps, and Gucci belt (all own)

Hawaiian shirts scream summer, vaccation, weekend. On the other side, it’s a shirt with a (Tropical) floral print. So, why limiting yourself to wear the piece just in one season. This post presents how you can wear Hawaiian shirts for work and in fall.

  1. How to Wear Hawaiian Shirts in Summer
  2. A Cargo Skirt plus Tropical Print Shirt Make a Great Season Transitional Look
  3. Tips to Get more Wear from Your Tropical Shirts
  4. Use Winter Blazers or Cardigans to Stay Warm

How to Wear Hawaiian Shirts in Summer

The easiest way to wear the iconic shirt is to pair it with cropped pants, shorts or a skirt. Well, think summer on Maui. All it takes is a solid color bottom that picks up one of the print’s colors like in the look below.

fashion blogger over 40 in a salsa dance outfit with tropical shirt
Jones New York Hawaiian print shirt with pink skater skirt, Michael Kors bag, Ivanka Trump cap-toe pumps, and Gucci belt


A Cargo Skirt plus Tropical Print Shirt Make a Great Season Transitional Look

Try to combine your Hawaiian button down shirt with a business casual pair of pants or skirt like in the example look below. As the shirt has some orange, I added an orange belt and orange plateau sandals. This outfit works well on a Friday in a casual work environment. The desaturated black and white make the outfit a classic with a pop of orange color. A perfect outfit to look professional at a work meeting during the dog days.

over 50 years old fashion blogger wearing a Hawaiian shirt and denim cargo skirt with plateau sandals as a summer work look for Casual Friady

style book author in cargo skirt, tropical print blouse, orange accessories
Vintage Hawaii silk shirt, cargo denim skirt, Michael Kors patent leather cork plateau sandals, Esprit shoulder bag, pearl necklace, Paloma Picasso xo belt (all own)

Do you know when and when not to add a pop of color?


Tips to Get more Wear from Your Tropical Shirts

When you live in a climate region where fall is short like in Interior Alaska, it is not worth investing into autumn clothes. Instead, try to cover the short fall intermezzo with a mix of summer and winter itemsfrom your closet. It’s a bit tricky when it come to a Hawaiian shirt that is an American summer classic. When you want to get more wear out of your fav summer blouse “winterizing” is a Must. This means adding pieces from the cold season wardrobe. To not look odd pick matching items in colors of the print that are of the darker group like the fuchsia cardigan.

influencer in Hawaiian shirt, cardigan, leather skirt, pantyhose fall look
Jones New York Hawaiian button-down shirt with Sofie cardigan, Gucci belt, Halogen leather skirt, Steve Madden plateau heeled loafers, and Kate Moss for Longchamp bag (all own)


In the example outfit, I am wearing my Hawaiian blouse from summer with a fuchsia cardigan and a brown leather skirt. The dark brown purple-red heeled loafers and fuchsia cardigan pick up the colors of the blouse’s floral print. I added a belt for shape and wore this outfit at work.


Use Winter Blazers or Cardigans to Stay Warm

For the commute to work I added my Burberry small plaid wool blazer. The brown of the blazer matches the brown of the skirt and bag. The blue and red of the blazer are the neighboring shades of the purple-red of the loafers. The scarf picks up all these colors and helps to tie the outfit together.

stylist with paisley scarf, leather skirt , plaid blazer
Burberry double-breasted blazer, Halogen leather skirt, Kate Moss for Longchamp bag, Steve Madden plateau loafers and matching silk cashmere paisley print scarf (all own)


Do you wear summer items in fall? How do you make them fall appropriate? How long is fall where you live?

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Photos: G. Kramm

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