There’s a reason the shirtdress is a perennial favorite—it’s polished, practical, and effortlessly chic. But like all good wardrobe staples, it deserves a modern refresh every once in a while. As we ease into spring, I’m embracing the return of the shirtdress—but with updated silhouettes, elevated accessories, and a little more polish than years past. Here’s how I’m styling it now, at 66, and why the shirtdress is once again a must-have for women who love timeless style with a twist.
👗 A Quick Fashion History of the Shirtdress
The shirtdress first rose to prominence in the 1950s, thanks in large part to Christian Dior, who reimagined men’s shirting into a feminine, cinched-waist silhouette as part of his iconic New Look. With its button-down front, collared neckline, and flattering A-line shape, the shirtdress offered women both structure and ease—something stylish, yet practical for the evolving post-war lifestyle.
Throughout the decades, it’s been a symbol of quiet confidence. The shirtdress has always walked that beautiful line between masculine tailoring and feminine grace, and that’s exactly why it’s endured.
Today, designers continue to reinvent the classic—shorter hemlines, unexpected fabrics, bold prints—but the bones of the piece remain the same: versatile, timeless, and effortlessly flattering.
The Return of the Shirtdress
Photo above: Maggy London Shirtdress | Similar Suede Espadrilles | Songmont Handbag | Bangles
Navy Shirtdress | Black Patent Leather Sandals | White Linen Jacket | Bamboo Handle Leather Tote | Caviar Spark Hoop Earrings
The Talbots Linen Shirtdress in Navy is a timeless warm-weather essential. It’s the kind of piece that works from brunch to boardwalk with just a change of accessories. I love it styled with espadrilles and a straw tote for casual elegance, or dressed up with gold jewelry and sleek sandals for a more refined take—and you know I love a dress that does double duty.
The Power of Structure
Gone are the days of boxy shirtdresses that overwhelm your frame. Today’s versions are tailored, belted, or subtly shaped to flatter your figure—whether you’re tall, petite, or curvy. I opt for dresses with defined waistlines or a self-tie belt that gives me control over the fit. I love how the return of the shirtdress manifests in modern silhouettes.
Above photo: Striped Shirtdress | Captoe Denim Slingbacks
Gingham Shirtdress | Similar Leather Belt | Canvas Espadrilles | Caviar Hoop Earrings
Style tip: I often swap the fabric belt for a structured leather one to add contrast and elevate the look.
Wear It Open as a Duster
One of my favorite styling tricks? Wearing a shirtdress as a lightweight jacket. Leave it unbuttoned and layer it over a monochromatic base (like white denim and a tank) for an easy, breezy third piece. It’s a perfect travel look or transitional outfit for spring days that start chilly and end warm.
Linen Shirtdress | Similar White Belt | Wedge Espadrilles | Straw Tote
The Frank & Eileen Rory Linen Shirtdress, which comes in multiple colors and stripes, is what happens when laid-back luxury meets impeccable tailoring. Made from their signature soft-washed Italian linen, this dress drapes beautifully and moves with ease—perfect for warm spring days or travel-ready wardrobes. Whether worn buttoned up with a raffia belt or layered open over a tee and denim, it’s effortlessly chic. The relaxed silhouette paired with premium fabrication makes it a staple for women who appreciate quality and casual sophistication.
The Return of the Shirtdress: How I Wear it Now
One of my all-time favorite shirtdresses is the Tobie from Anthropologie, which comes in solids, stripes, and patterns. Add a straw fedora, straw handbag, and sandals, and you’re ready for the weekend!
Sleeveless for Layering
Sleeveless shirtdresses make the perfect layering base. Try a white poplin style under a lightweight cardigan, denim jacket, or linen blazer. It’s feminine, sharp, and versatile enough for everything from lunch with girlfriends to casual Fridays at the office.
Style Tip: Elevate the Pomander Place White Jules Dress with a raffia belt and nude sandals to define your waist and elongate your silhouette. But I love the modern silhouette all on its own.
Don’t Be Afraid of Color
While navy and white are timeless choices, I’m currently loving fresh spring shades like soft olive, cornflower blue, or even a bold stripe or pattern. A pop of color brings energy to the look while keeping the silhouette grounded and elegant.
Above photo: Cornflower Blue Shirtdress | Acrylic Sandals
Denim Shirtdress | Suede Espadrilles
The Talbots Denim Shirtdress is the kind of wardrobe hero you’ll reach for again and again. Its tailored silhouette and soft indigo wash strike the perfect balance between polished and relaxed. Dress it down with sneakers and a crossbody bag for weekend errands, or pair it with heeled sandals and statement earrings for a casual dinner out. It’s timeless, versatile, and effortlessly chic.
Closing Thoughts About the Return of the Shirtdress
Whether you wear it buttoned up and belted or open and flowing like a duster, the shirtdress is a piece that works for every woman, at any age. It’s classic style reimagined for real life—and that’s always in fashion.
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