We’re kicking off a brand-new monthly series called The Classics Reimagined—and I couldn’t be more excited to bring this to life for you. Our inaugural post is all about Shirtdress Styling Ideas with: The Classics Reimagined: How to Make a Shirtdress Feel Brand New.
Why This Series?
Because style isn’t about chasing trends—it’s about building a wardrobe that works hard and looks good year after year. And let’s face it, the real magic happens when you take a timeless piece and give it your own personal twist. Each month, we’ll highlight one tried-and-true wardrobe staple and explore fresh, updated ways to wear it. This series is about showing that the classics never go out of style—they get better with age, just like us.
We’re starting with one of my warm-weather favorites—the shirtdress.
Seersucker Shirtdress from Talbots
When it comes to warm-weather style, few pieces check all the boxes like a great shirtdress. It’s tailored but easy, structured but breathable, and effortlessly transitions from late spring into summer. Whether you’re heading to lunch with friends, strolling the farmers’ market, or packing for a weekend getaway, the shirtdress is one of those timeless staples that make getting dressed feel effortless.
The Origin of the Shirtdress
The shirtdress was popularized in the 1950s, thanks in part to Christian Dior, who reimagined the traditional men’s shirt into a full-skirted dress that celebrated the feminine silhouette. But the origins go back even further—to the early 20th century, when utility met elegance. Women began borrowing elements from menswear—collars, cuffs, buttons—and tailoring them into styles that were both practical and chic.
It all started in the 1950s, when the iconic silhouette made its debut on television screens and in suburban kitchens. Cinched at the waist, buttoned just so, and paired with a strand of pearls, the shirtdress was every TV mom’s uniform—equal parts housewife and heroine. June Cleaver didn’t just raise boys—she raised the bar for polished daywear.
Since then, the shirtdress has stood the test of time, appearing in everything from Audrey Hepburn films to modern-day street style. It’s a piece that can be as structured or as relaxed as you like—and that’s the beauty of it.
Today, I’m sharing three fresh ways to style the shirtdress for the season ahead—each with a slightly different vibe but all grounded in polished, modern elegance.
1. Refined: Belted and Polished
Let’s start with a classic approach: cinch the waist with a belt. Whether you’re using the fabric belt that comes with the dress or swapping in a leather or woven one for contrast, belting adds instant definition and elevates the entire look. Pair it with heeled sandals or block heels, and you’ve got the perfect brunch or casual dinner outfit.
Striped Shirtdress | Captoe Denim Slingbacks | Similar Tote
This blue and white Striped Shirtdress is the definition of crisp, classic style with a coastal twist. The self-tie belt creates a flattering silhouette, while the three-quarter sleeves and midi length make it perfect for warm days with a breeze. I styled it with Captoe Denim Slingbacks and a structured two-tone tote—a look that feels polished yet relaxed, ideal for seaside strolls or lunch by the water.
Shirtdress Styling Ideas
Try a wide statement belt with a solid dress to create shape and visual interest.
Gingham Shirtdress | Similar Leather Belt | Canvas Slingback Espadrilles | Caviar Hoop Earrings
Yes, you can give a relaxed shirtdress a polished look! This classic gingham shirtdress is a beautiful example of timeless summer style. The neutral palette keeps it grounded, while the structured ivory belt adds definition and polish. I paired it with slingback espadrille flats for a comfortable yet refined finish—perfect for everything from an oceanside stroll to dinner on the deck.
Cornflower Blue Shirtdress | Acrylic Sandals
A Cornflower Blue Shirtdress from Talbots is a fresh twist on a classic silhouette with its drop waist. It’s bright, breezy, and perfect for spring. The soft hue adds a subtle pop of color, while the tailored shape keeps it polished. I paired it with clear acrylic sandals for a modern, lightweight finish that feels effortless and on-trend. It’s the kind of outfit that looks put together but takes almost no effort at all.
Shop the Shirtdress Collection
2. Casual: Open and Layered
One of my favorite ways to reimagine a shirtdress? Wear it open as a lightweight duster or layering piece. Toss it over a tank and slim jeans or shorts, and suddenly you have a casual yet pulled-together outfit. Add slides or fashion sneakers and a structured bag, and you’re ready to go.
Linen Shirtdress | Perfect Fit Tee | Slim Straight Jeans | Wedge Espadrilles
Shirtdress Styling Ideas
This works beautifully with linen or gauze shirtdresses that have a bit of flowy movement.
On YouTube…
Spring Dress Inspiration
Speaking of YouTube…
Did you know we have a YouTube Live program each week? Join Kelly and me for live conversations about a variety of topics relevant to life today, and all things fashion – including try-ons, regular and petite styles, and so much more! We want you to join the conversation with your questions, thoughts, and experiences.
So be sure to tune into my YouTube channel Sunday, May 25, at 5 PM EST. for our YouTube Live! This week’s topic is our Summer Kickoff: Favorite Travel Outfits + Outdoor Plans.
3. Relaxed: With Sneakers or Espadrilles
Yes, you can absolutely pair a shirtdress with sneakers or espadrilles, and it looks effortlessly chic. This combo is my go-to for travel days or casual weekend errands. Choose a linen or chambray shirtdress and keep the accessories casual: think a crossbody bag, sunglasses, and a fun pair of white sneakers or neutral espadrilles for an easy, comfortable finish.
Cross-Dyed Linen Shirtdress | Suede Espadrilles | Marais Stretch Belt | Suede Shoulder Bag | Gold Hoop Earrings | Alternative Statement Necklace | Caviar Bangle | Caviar Watchband
This look is all about casual elegance with a soft, neutral palette. I’m wearing a lightweight linen shirtdress, it’s easy, breathable, and perfect for warm weather. A tan belt adds shape at the waist, while the textured espadrilles and suede hobo bag keep things laid-back and comfortable. The oversized statement necklace adds just the right amount of personality. It’s the kind of outfit that looks effortless, but feels completely put together. See how this dress works for petites in our post: Spring Dresses For Any Occasion.
Shirtdress Styling Ideas
Roll the sleeves and pop the collar for an extra dose of effortless style.
Madewell Linen Utility Shirtdress | Sam Edelman Mackie Mesh Espadrille Mary Jane
This Linen Utility Shirtdress from Madewell is the definition of easy summer dressing—lightweight, breathable, and cut in a relaxed silhouette that keeps things simple and stylish. The button-front detail and utility-style chest pockets give it a little structure, while the natural fabric keeps it feeling casual. Kelly paired it with black espadrille Mary Janes for a touch of contrast and texture. It’s perfect for mornings in the garden or casual weekends on the go.
Our Favorite Brands for Shirtdresses
Closing Thoughts
Shirtdress Styling Ideas
The beauty of the shirtdress is its versatility. It’s a classic one-and-done outfit, but it can do the work of three pieces depending on how you style it. And no matter your personal aesthetic—classic, modern, casual, or polished—there’s a version of the shirtdress that’s just right for you.
Let me know in the comments how you’re wearing your shirtdresses this season. And stay tuned for the next edition of The Classics Reimagined—because style is never one-size-fits-all.
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