Styling High Waisted Sailor Shorts Outfits

Ahoy! Shorts 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  sailor shorts outfits I’ve put together, include 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 that I have longer legs.  Also, because they nip in at the waist and flare out to an A-line shape, they make 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 elegant compared to most. They’re perfect for midlife fashionistas!

sailor shorts purple tee

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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

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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 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 cantelope color looks so fresh with white too, don’t you think?

sailor shorts orange flutter tee

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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 2024 because of the wide shoulders and ruffle sleeves.

The nice thing about this modern shape is the wide ruffle sleeves mirror the wider A line white shorts, giving you a curvy hourglass shape.

sailor short blue striped top

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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 outfit 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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