14 Ways to Wear a Classic Shirtdress

With Knee High Boots

A simple white shirtdress gets a sexy makeover when it’s a mini paired with knee-high black leather boots.

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Wrap with Sandals

A striped wrap shirtdress is a standout classic that doesn’t need much styling to shine. A sleek pair of slides and a top handle bag are all you need with this piece.

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Under a Strapless Minidress

Shirtdress- Under mini dress — Getty Images

While a shirtdress can be worn alone for a full outfit, it can also be artfully layered with other pieces to create a whole new look. Here, a bright shirtdress under a strapless denim dress changes the style completely.

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With a Tie and Sequins

Shirtdress- Tie and Sequins — Getty Images

Another layered shirtdress look with so much added flair! From the sequined mini to the skinny tie, this look is ready-made for a dazzling night out.

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With a Tuxedo Jacket

Shirtdress- Tuxedo Jacket — Getty Images

No formal, stuffy tuxedos here—just the coolest textured jacket thrown over a shirtdress and boots for the coolest, wear-anywhere outfit.

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Bright Red

A shirtdress in as bold a color as this asymmetrical scarlet version only needs a pair of heels to show it off—the matching red lip doesn’t hurt either!

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Under an Overalls Dress

Shirtdress- Under Overall Dress — Getty Images

Here’s another, more casual way to layer two dresses: a shirtdress under a corduroy overalls dress. We love how the shirtdress pops out on the bottom here, and the knee-high white boots complete the look.

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Lace

Typical shirtdresses usually have more of a workwear feel, but by switching up the material to something delicate like lace, the look takes on a new, romantic vibe that would be perfect for a date or bridal shower.

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With Fuzzy Shoes and Socks

Shirtdress-fuzzy shoes and socks — Getty Images

For the ultimate casual and cool execution of a shirtdress, try this combo: patterned socks, fuzzy shoes, and a pop of color with a comfortable, loose-fitting dress.

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All Black and Polished

This unembellished, shirtdress version of the little black dress is anything but boring. Instead, with matching pumps and a small bag, it’s the chicest way to dress for a busy day of meetings.

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Off the Shoulder

The button-up style of a shirtdress means you can play with the neckline in unexpected ways. Try layering over a tank and pulling one shoulder down as seen here.

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With a Cardigan

Shirtdress- Under a cardigan — Getty Images

It’s easy to lean into a bookish vibe with a shirtdress. Paired with a cardigan, high socks, and oxfords, a shirtdress can take you back to your school days in a modern way.

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With a Leather Jacket

Shirtdress- Leather Jacket — Getty Images

This is the ultimate in edgy and effortless: an oversized leather jacket, a sleek shirtdress, and a classic ankle socks and loafers combo to complete the outfit.

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Under a Sweater

Shirtdress- Under Sweater — Getty Images

In the same way you might layer a blouse under a chunky knit sweater, the concept works with a flowy shirtdress just as well for a complete outfit once you add a pair of barely-there sandals (or swap for booties if it’s chilly).