How to Style a Button-up Shirt in 20 Classy Ways

10 Minutes

I just got back from a trip and somehow I managed not to take my very favorite wardrobe staple, the button-up shirt!

So this is a kind of homage or apology to it and an opportunity to show you how to style a button-up shirt in multiple ways.

My shirt is linen, so all these looks have a summer vibe. I hope you get some great styling ideas from them.

Basic 90s

1. Basic 90s

Tie the shirt as a crop top, add wide leg jeans and sneakers and big sunglasses.


2. Preppy

This look requires crop tan pants, brown moccasins and a French tucked shirt. And of course, a preppy shoulder bag.

French Riviera chic

3. French Riviera chic

Keep the pants but swap the moccasins for ballerina flats. Tie the shirt in the front and add a sunhat and a great pair of shades.

Head-to-toe volume

4. Head-to-toe volume

Wear the shirt open over a crop or bikini top. Finish your look with wide leg black pants and sandals and your preppy shoulder bag.

Wrap silhouette

5. Wrap silhouette

Wrap the open shirt across your body and tuck it into those same black pants. Turn up the collar for extra impact.

Bustier silhouette

6. Bustier silhouette

Button-up the shirt under your arms and tie the sleeves in front.

The crop top preserves your modesty but tuck the straps inside the shirt. Dress this one up for evening with a smart bag.

Monochrome columns

7. Monochrome columns

Slip a silky chemise under the open shirt, throw your preppy bag over your shoulder, and you’re good to go.

For the office

8. For the office

Tuck the shirt into smart ankle length white or cream pants. Add nude heels and a navy bag for a professional look.


9. Romantic

Front crop tie the shirt and add some gorgeously romantic floral pants and those nude heels for a beautiful date night.

Texture mix

10. Texture mix

French tuck the shirt into the floral pants and pop on some pastel ballerina flats.

High contrast

11. High contrast

Back to a more casual look with cropped white pants, a sun hat and flat, strappy sandals.

High contrast two

12. High contrast two

Front tie the shirt, keep the pants and shoes and you have another look.

High contrast three

13. High contrast three

Swap the flat sandals for black high wedges and the straw bag for a black and white shoulder bag.


14. Tonal

Tuck the shirt into paper bag top denim shorts and pop on your ballerina flats. Add a heavy brown leather belt for casual with class.

Slouchy styling

15. Slouchy styling

Another casual look, this time with the shirt worn loose over tan shorts. A ball cap and shades give a real summer vibe.

Preppy shorts

16. Preppy shorts

Smarten it up with a chunky brown leather belt and moccasins. Tie the shirt into a crop top.

Casual and tonal

17. Casual and tonal

The classic casual summer look. A white t-shirt tucked into straight leg jeans, shirt worn as a jacket, topped off with a ball cap.


18. Classic

Tuck the shirt into those straight leg jeans and complete the look with your choice of bag and shoes.

Work 2.0

19. Work 2.0

You can take this look from office to date night. Tuck your button-up into a flowy, silky skirt, throw on some nude heels and add a smart bag.

Tonal layers

20. Tonal layers

Tie the shirt over a slim column dress in a pale color. Add flats for a cool summer look.


Bonus look

And of course, your button-up makes the perfect beach cover up over a bikini or swimsuit.

How to style a button-up shirt

I hope you got some inspiration from at least some of those looks. I so enjoyed putting them together! Did you imagine a plain navy linen shirt could be so versatile? 

Start with whatever you have in your closet and see how many looks you can get by combining them in new ways.

I’d love to know which was your favorite styling out of all these - please drop me a comment below.

Next, learn 4 Sleek Style Hacks Inspired by Men's Fashion.

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