Spring & Summer

How to Style Sailor Shorts: 3 Cute Outfits

Ahoy! Short season is upon us, and one of the most flattering new styles has a sporty, nautical vibe. Check out these chic high-waisted shorts outfits I’ve styled for you, and let me know if you’re on board!

sailor shorts purple eyelet tee

Sailor Shorts Outfit #1 – Eyelet Sleeve Tee

Each of the four ailor shorts outfits I’ve put together includes these fabulous white nautical-style shorts from @talbots. I love these button shorts for so many reasons.

For one, they are high-waisted, which creates the illusion of longer legs. Also, because they nip in at the waist and flare out to an A-line shape, they do a great job making my waist look small.

They have a 5-inch inseam, so they are not too short, and they are very comfy because they are made from a cotton/linen blend.

The gold military buttons are such a classy detail, and the overall tailored look of these shorts makes them more elegant than most. They’re perfect for midlife fashionistas!

sailor shorts purple tee

 

How do you like this modern orchid tee I’ve styled them with? This light, cool purple color is fabulous, and the split neck and eyelet sleeves add such a pretty, feminine touch.

 

sailor shorts yellow linen top

Sailor Shorts Outfit # 2. – Linen Tie Shirt

A linen top also looks very natural and summery with these white sailor shorts. This striped yellow linen top ties easily at the waist for a relaxed, breezy look.

sailor shorts yellow tie front shirt

Shop the look

 

Add a straw bag and some gold sandals for the perfect upscale shorts look.

 

sailor shorts orange top

Sailor Shorts Outfit #3  – Flutter Sleeve Top

Here’s a lovely top with wide, flowy, pleated sleeves (similar) that gives these classic shorts a modern look. This is a great top if you want a little arm coverage, but hate anything too fitted. The cantaloupe color looks so fresh with white, too, don’t you think?

sailor shorts orange flutter tee

I’ve added a slouchy straw tote and straw sandals to this shorts outfit to give it a beachy look.

 

sailor shorts striped tee

Sailor Shorts Outfit # 4 – Striped Muscle Tee

I couldn’t share these shorts without styling them with something classic like a striped sailor tee. This one looks very 2020 with its wide shoulders and ruffle sleeves.

The nice thing about this modern shape is that the wide ruffle sleeves mirror the wider A-line white shorts, creating a curvy hourglass silhouette.

sailor short blue striped top

The layered ruffle sleeves are also just very pretty. They’re trimmed in satin.

So what do you think of high-waisted sailor shorts? How do you like the look, and did you know how well they can flatter a mature figure? Which of the four sailor shorts outfits was your favorite?

To shop this look, click the links under the photos. Bonus!! Everything is on sale for the July 4th weekend!

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Meet the author

Deborah Boland

Deborah Boland is the founder of Fabulous After 40 and a certified image consultant with decades of experience in fashion and personal styling. She brings a modern, refined perspective to getting dressed — helping women look polished, confident, and effortlessly modern.

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