Every so often, I love going down an image archive without much sense of direction. It's how I discovered Princess Anne was an underrated royal style icon and that fashion week in the 1980s was oh so glam. Sometimes I end up with random style inspirations or outfit ideas, and other times, I strike gold—like when I discovered these vintage photos of celebs playing tennis. But first, let me rewind to tell you how I came across them.
Tennis has always been counted among the most fashionable of sports. Anna Wintour is often spotted at major games, Serena Williams has broken countless barriers with her on-court style, and Stan Smith trainers (Phoebe Philo's fashion renaissance shoes) are named after the tennis pro. Royal fashion favourites Kate Middleton and Meghan Markle attended Wimbledon together last year, and you'll often find fashionable couples (cough, noughties Jude Law and Sienna Miller) cuddling in the stands.
When Lousie Trotter—formerly at the helm of Joseph—was made creative director at Lacoste last year, I made a mental note of the connection between Trotter's minimalistic mind and Lacoste's heritage. The marriage made sense, and months later, her debut collection brilliantly reimagined Lacoste's tennis signatures in a similar way that Daniel Lee did with Bottega Veneta's iconic woven leather. It felt like fashion was about to have a tennis moment.
From pleated skirts and polo shirts to all-white outfits and beige hues, there's a perennial cool to tennis style fixtures that feel acutely on trend for 2019. So as I always do, I decided to look back through vintage photos to inspire my summer 2019 aesthetic. This is when I found these fashionable interpretations of classic tennis outfits worn by some of our favourite celebrities. The fact that they're not entirely practical as an actual pro tennis player's outfit is what makes them that much more fabulous. Keep scrolling to see the photos and my vintage-inspired shopping picks.
Style Notes: The rolled-up sleeves, the wrist band, the raised pinky… Every detail of Farrah Fawcett's tennis look is top-notch fashion.
Style Notes: Since she was dating tennis star Andre Agassi at the time, it's no surprise that Brooke Shields made this '80s tennis fashion moment happen.
Style Notes: In a rare moment out of her iconic trousers, Katharine Hepburn dons mini shorts with a thin roll-neck top and canvas shoes.
Style Notes: True to her glamour, Diana Ross pairs her polo and headband with gold earrings.
Style Notes: This Elton John outfit literally spoke for itself during a game against Billie Jean King.
Style Notes: Even leaving the gym, Princess Diana is a fashion inspiration. Her pale hues are so dreamy.
Related: Princess Caroline's Royal Style Needs Your Attention Right Now
Style Notes: Fashion designer Mary McFadden wears a tennis set of her own design (featuring her legendary pleats) with a black cap.
Style Notes: Janet Leigh and her daughter, Jamie Lee Curtis, ooze Hollywood glamour in their accessories alone.
Style Notes: Whether she played or not, Barbra Streisand in a bucket hat is so perfect.
Style Notes: Princess Caroline, a style icon in her own right, goes royally classic in an all-white ensemble.
Style Notes: Joan Crawford layers a knit vest over a polka-dot shirt with a white midi skirt and lace-up sandals.
Shop My Vintage Tennis–Inspired Shopping Picks
Up Next: More and More Fashion Girls Are Buying These Vintage Earrings
-
From Bella Hadid to Vogue Staffers—These Are the 10 Insider-Approved Vintage Stores in NYCNo gatekeeping here.
-
The Women Behind Instagram's Designer-Vintage CrazeI suggest you get to know them.
-
Elsa Hosk's Jeans-and-Flats Combo Screams "Fashion Insider"Model off duty at its finest.
-
Dakota Johnson Wore a Thong-Baring Sheer Dress to the SNL After-PartyEven better, it's vintage Alaïa.
-
It's a Good Time to Be a Vintage J.Crew Fan, Thanks to These 12 Chic PiecesI'm in my Carolyn Bessette-Kennedy era.
-
For Latinos, Grandma's Gold Rings Aren't Just an Aesthetic—They're a CultureRead the powerful stories behind these families' most precious pieces.
-
I Love Gifting Special Jewelry for the Holidays—Shop My Latest Finds HereThe most authentic pieces on the market.
-
Every Cool Item I Tried, Discovered, and Loved From a Week of ThriftingAs well as helpful tips and tricks.
