Whether you find yourself lamenting the reported demise of the floral dress or steadfastly wearing yours, a noticeable trend shift from dresses to relaxed separates—like wide-legged linen pants, coordinated sets resembling pajamas, and abundant loose denim—has emerged in the display windows of my local shops. Though I’m currently distancing myself from patterned midi dresses, this shift creates a gap in my wardrobe. What’s suitable for a workday filled with meetings, an art gallery afternoon, or a friendly lunch that may extend into the evening?
Enter the updated shirt dress, specifically the MSD—maxi shirt dress, which grazes the ankle. Jennifer Lopez, who celebrated her 55th birthday by biking to a luncheon in the Hamptons, was recently spotted in a Dior maxi shirt dress of sheer fabric adorned with a green-on-white print. Its steep $3,400 tag is noteworthy, especially given the proximity of its delicate fabric to a bicycle chain. Simultaneously, Celine Dion opted for a similar Dior shirt dress in Paris; hers in black, voluminous and retaining the cinched waist reminiscent of the 1950s “shirtwaist” designs.
“They’re ideal for a loose fit paired with flats, and they transition seamlessly from a beach cover-up to an evening outfit by simply swapping accessories,” notes fashion stylist Esperanza de la Fuente.
While traditional shirtwaist dresses typically ended just below the knee, posing difficult footwear choices and a decidedly daytime feel, an ankle-length shirt dress is versatile enough for flats or heels. It can be dressed up for evening engagements, not just on vacation but also in urban or professional settings. The length and silhouette lend a refined yet effortless vibe. Both Lopez and Dion styled theirs with minimalistic jewelry and sleek hairstyles to highlight the dresses’ understated elegance. With this summer’s preferred ballet flats (as worn by Lopez) or slightly more formal slingbacks (as Dion did), an MSD proves to be a wardrobe staple for the remainder of the summer and beyond, adaptable with additional layers as the season changes.
“Add simple black flip-flops, rolled-up sleeves, standout rings, a large woven leather bag, and black sunglasses for an effortless day-to-night look,” suggests Lizzy Hadfield, a social media influencer and book club host.
The practicality of a button-through MSD allows for quick adjustments to the fit—button up for more coverage or unbutton for a relaxed look. Anne Hathaway demonstrated this versatility in May with a white cotton shirt dress from Gap, priced at £120. Worn with a high slit and partially off the shoulder for a red carpet event in Rome, her look showcased the adaptability of MSDs, easily styled with a belt, open collar, and eye-catching jewelry for evening occasions.
For those of us not in Paris, the Hamptons, or Rome, but coping with a muggy British summer, stylist Monikh Dale recommends, “Letting it hang straight—no belt needed. Add a large stone necklace for a touch of elegance, simple flip-flops for understated chic, and a suede bag.”
If the classic cinched waist isn’t your preference, consider a shirt dress with cleaner lines that echo a man’s tailored shirt elongated to the floor, offering a relaxed fit with equal versatility. Katie Holmes exemplifies this style, wearing a long-sleeved, black Banana Republic MSD open over a tank top and light pink trousers, effectively a light duster coat for warm days.
To find the ideal MSD, consider fabric choices: structured materials like cotton maintain shape and suit angular or tall figures, while softer fabrics offer a flattering drape for curvier forms. Proper ankle length is crucial and might require some searching or alterations, especially for taller individuals. Opting for brands known for longer cuts or visiting a local tailor to achieve the perfect hemline ensures your MSD complements your style and silhouette, making it a versatile addition to your wardrobe.
