Even though we would never see someone wearing this look today, we have to admit that it’s pretty iconic. This photo shows Mrs. Raine Legge, the future Countess Spencer, attending Royal Ascot in 1949. Her hat and handbag are adorned with fake grapes and cherries, which isn’t typical for an Ascot look. The photo is in black and white, but we can only imagine how colorful and fun this outfit was in person.
If the surname “Spencer” sounds familiar, it’s because it belonged to none other than Diana, Princess of Wales. When this photo was taken, Raine had no idea that she would one day become the stepmother to one of the most famous members of the Royal Family.
Mr. and Mrs. Ronald Armstrong-Jones Arrive
The who’s who of the British upper crust has always attended Royal Ascot week. From the Queen and King to political figures, this event is one of the most prominent places to make an appearance. Barrister Ronald Armstrong-Jones attended Royal Ascot with his second wife, Carol Akhurst, in 1945. The couple looks like the perfect 1940s couple with their fancy outfits.
Carol wore a gorgeous knee-length dress with tulle, ruffles, and delicate layering. Royal Ascot dresses were more minimalist during World War II due to rations and the need to appear less opulent during wartime. Carol’s dress reflects the era’s more parred-down aesthetic, but it’s still a beautiful and well-made dress. She finished off her look with a cloche hat and a bold statement necklace.
A Fashion Girlie: 1940s Edition
This photo shows someone named Elizabeth Shelley dressed to the nines for the 1948 Royal Ascot. We don’t know exactly who Elizabeth Shelley was, but we have a feeling she was the fashion girlie of her era. Her look is so unique that you know this woman was into dressing up and experimenting with fashion. Her dress calls back to the early fashion of the 1900s and 1910s with its snatched waistline and smocked neckline.
Her hat is retro for the time, too. We love a throwback fashion moment. Also, look at those shoes. The heel is so cool and unique. We want our own pair, Elizabeth! To complete her retro outfit, it looks like Elizabeth also brought along a parasol, which was all the rage at the turn of the century.
A Checkered Hat for Mrs. Black
This vintage Ascot photo is so fun and iconic. It’s of a certain someone named Mrs. Peter Black, who was a fashion icon in British society. This look is a fun twist to the more muted and somber fashion trends of the 1940s. Mrs. Black is wearing a typical 1940s WWII-era dress and gloves, but her Ascot hat makes her stand out.
The black and white checkered hat is larger than life and oh-so-chic. The brim of the hat frames her face and hair perfectly and is definitely the centerpiece of this outfit. She finished off her classy look with pearl earrings, a pearl necklace, and somber black gloves.
Nowadays, everyone talks about celebrity sightings at the annual Met Gala in New York. However, this 50s-era Ascot photo proves that celebrity sightings at fancy events are nothing new. British sensation Sabrina attended Royal Ascot in this frothy 50s gown. Sabrina was a gorgeous model and actress whose look was very obviously influenced by Marilyn Monroe.
Sabrina attended Royal Ascot in this fit and flare, off-the-shoulder dress that looks like a spring day. There are flower appliqués along the A-line skirt, and the dramatic neckline certainly doesn’t leave much to the imagination, at least by 1950s standards. Sabrina’s hat is just as dramatic as her dress, with a wide, sheer brim that gives garden party vibes. The famous model wore cute, subtle accessories, including simple white heels and a wicker handbag.