15 Chic Ways to Style a Shirt Dress: Outfits and Ideas

Shirt dresses are a classic style inspired by the silhouette of a man’s button-front shirt. Although they can sometimes seem a little plain and shapeless on the hanger, they are chic and versatile in your closet. Here are ten easy ways to style a shirt dress you might not have thought of.

1. Wear a Shirt Dress with Heels, a Clutch, and Bare Legs

If you want to look sexy in a shirt dress, this is the way to do it.  Heels and bare legs with a short, sassy shirt dress will make it look like you grabbed your hubby’s shirt and didn’t bother with pants.

Make sure your legs look attractive bare because this way of wearing a shirtdress does not look good with pantyhose.  It’s fair to say that the older you are, the trickier this look is. If you think it can work for you, keep it classy by adding a sophisticated clutch, designer shoes, and some high-end accessories.

tan shirtdress white booties

2. Try Bootie with a Shirtdress

Booties can also look super cute and modern with a Shirtdress; don’t worry; it won’t be a clunky look. Sleek leather or suede booties with a pointy toe elongate the legs and give you a chic look.

Blue Striped shirtdress, sneakers, pink bag | styled by Fabulous After 40

2. Pair a Shirt Dress with Sneakers

Sneakers with a shirtdress are cute, comfy, and much easier to wear in middle age than heels. Choose lace-up or slip-on statement sneakers. The thicker the sole, the trendier the look.


striped shirtdress


3. Layer a Shirt Dress over Leggings or Skinny Jeans

If you feel your shirt dress is too short to wear as a dress, wear it as a tunic shirt with leggings. Black or white leggings are usually best. Avoid patterns even if you are wearing a solid-colored shirtdress. They don’t look classy.

4. Slip a Long Vest over a Shirtdress

A long sleeveless vest in a neutral color worn over a solid color shirtdress or a print shirtdress such as a stripe or floral can look very chic

5. Ubutton Your Shirtdresss

Use your shirt dress as a layering piece, wearing it partly unbuttoned to reveal a camisole underneath or open like a long jacket.  It’s very feminine when you are strategically undone, and when you wear it with a  belt or tie waist, it creates a feminine, figure-flattering silhouette.

6. Throw a Jean Jacket Over a Shirtdress

A cure jean jacket or cropped boyfriend blazer looks cute and perky with a Shirt Dress.

Shirtdresses - Pink Sleeveless, white accessories | styled by Fabulous After 40

7. Choose a Fit and Flare Shirt Dress if You are Pear-Shaped

If pear-shaped, choose a shirt dress with an A-line or flared bottom. A regular shirt straight-cut shirt dress may be too tight across the hips.

8. Pair Skinny Jeans with a Shirtdress

Skinny jeans that grab the ankles are like leggings and can look great with a crisp cotton shirt dress with a collar. Heels look great with this chic duo.

blue fit and flare shirtdress

9. Roll up Your Sleeves to Look Sporty

Push or roll up your sleeves to create a youthful and sporty 3/4 length. Some shirt dresses come with roll-tab sleeves, which are ideal.

10. Combine it with a Boyfriend Cardigan

A long cozy boyfriend cardigan can be an excellent layering piece for a shirt dress, especially when the shirt dress is on the silky side.

11. Switch Out the Self-Belt for a New Vibe

The self-belt that often comes with a shirt dress can make your attire seem average and not so figure-flattering. Try a different leather, chain, or rope belt to add style.

Yellow Floral Maxi shirtdress

12. Wear a Shirtdress with Flat Sandals

Many shirt dresses are on the short side, which is why they look good with flats.

Olive Short Sleeve Shirtdress

13. Try a Collarless Shirt Dress

Collarless shirt dresses are a softer take on the look (perfect for more feminine styles.

Shirtdress - White

14.  Add Feminine Jewelry For Balance

Balance the masculine vibe of a shirt dress by wearing pretty jewelry, a beautiful bag, and some sexy sandals or feminine shoes.

Navy Polka dot shirtdress, white accessories | styled by Fabulous After 40

15.  Hourglass? Avoid Boxy Shirtdresses

If you have a defined waist, choose a shirt dress with a slight taper at the waist to avoid looking shapeless and bulky. A drawstring waist will give you shape too, or belt your waist.

What do you think? Are you ready to give a shirt dress a go?

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4 thoughts on “15 Chic Ways to Style a Shirt Dress: Outfits and Ideas

  1. You always put the cutest things together. I did laugh at the unbuttoned dress. I have done that. Thanks for all the great ideas.

  2. Thanks for the ways to style a shirt and dress. I bought one in plain navy last fall and knew it could be a workhorse, but this gave me some new options! Thanks so much!

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