14 Ways to Wear a Classic Shirtdress

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Women wearing shirtdresses — Photo:
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The shirtdress is an undisputed fashion hero piece: an effortless one-piece outfit that works in any professional setting and manages to be both timeless and currently on-trend. It’s elegant and refined enough to make a full outfit on its own, but adaptable enough that it can be styled accordingly for various occasions from brunch dates to boardroom meetings.

While we’d never call a shirtdress on its own boring, it can serve as the perfect canvas for creative layering and styling. Whether cinched at the waist with a belt for a more defined silhouette, worn under a sparkly dress for a night out, or layered over jeans for a playful twist, this fashion staple pairs well with so many other pieces in your wardrobe.

Not sure how to wear yours? We’ve pulled together 14 ideas for how to wear and style a shirtdress no matter what you have planned for your day.

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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).