My favorite time of year just got better - everyone watched Challengers and wants to dress like a tennis player. This is great for a few reasons -
a. It’s a very chic look and looks fabulous with a tan
b. I am VERY good at dressing like this
Proof, you ask? I attended high school from 2008-2012, considered myself a Blair (owned between 15-20 headbands at any given time), actually played tennis, and owned (and read) the book Classy by Derek Blasberg. I even went so far as to attend university in the Northeast (kidding, but not really - this was the heyday of Lily Pulitzer and Jack Wills. Mistakes were made). Though much of that has fallen out of favor, starting my country club prep look early gave me loads of time to perfect my craft.
I am not the right person to go terribly deep on prep theory (though pour me a glass of chablis and I’ll go on for hours), but for brevity’s sake, we will not be discussing Southern prep, New England prep, Ivy Prep, coastal California prep, or European / British prep - we will be specifically discussing country club prep, with roots that go back centuries but a look that is both immediately recognizable and timeless, and is at home in Beverly Hills just as much as Greenwich.
Country club prep (or Challengers core if you have worms in your brain like me and think it’s truly hilarious to be reductive in low stakes situations) is keenly focused on crisp whites combined with sky or navy blue, black, khaki, army green, and the occasional pop of canary yellow or poppy red (ideally in the form of a diamond and nails, respectively). We’re going for clean lines, strong tailoring, and a delicate balance between feminine and sporty.
Challengers core, like its preppy grandparents, requires situationally specific dress. This means if you are going to play tennis, you wear a proper tennis dress, carry a proper tennis bag, with a proper tennis pullover. Same goes for golf. What this also means, in my humble opinion, is that you shouldn’t wear an actual tennis skirt to do anything other than play tennis (or a brief drink or sandwich DIRECTLY following your last set). This is where people get it wrong - it’s a huge mistake to pull a look directly from the courts. What we want is inspired pieces, that reflect this muted color palette without devolving into costume.
I think this is a good time to tell you about one of my top rules for dressing that I have held to for the last 15 years, almost without fail (though recently learning it is a French tip - go figure!) - in any outfit, do not combine more than three main colors in an outfit. In interior design, we call this the 60 30 10 rule, which translates to utilizing one color is 60% of your room, another for 30% and an accent color for 10%. If I am wearing a white top and white skirt, I’ll typically go for a nude bag and nude shoe, and black sunglasses.
One of these days we’ll delve into color theory but that’s another conversation entirely.
Let’s have a pop quiz to make sure this is really sinking in for you - but do be warned I did not wash my face or brush my hair for this.
Is this Challengers-inspired outfit any good?
Yes it works! Combining the masculine influence of a mens rugby shirt with a short pleated skirt feels both sporty and feminine.
Is this Challengers-inspired outfit any good?
Yes, it’s perfect! The colors and shapes play well together - we have tied and pleated dress, matching bag, and all the right accessories.
Is this Challengers-inspired outfit any good?
Yes! Even though we’re a little more bold with the bright red, the shape of the dress and matching shoes keep it sophisticated.
Finally - how to get the look
Short, structured dresses
The shorter and more structured the better. Bonus points for a pleat, pinstripe, or waist tie.
Maje, on sale for 30% off
Proenza Schouler, on sale for 60% off and is the color of a tennis ball, perfect!
90s sunglasses
Oliver Peoples via The RealReal
Arm party
I was recently inspired by an older woman I met at a wedding welcome party wearing what I later learned was $15,000 on her wrist in the form of an old school charm bracelet. You can visit Charm Co to steal her look, my favorites include the thinker, cowboy hat, champagne bucket, and birdcage.
I have been wearing my Cartier Panthere for the last five years and don’t plan on stopping now. If you’re willing to go big, it’s a great investment. If not, I love and own this Timex at a much more reasonable $65.
You should lean fairly delicate with the rest of your jewelry, I am partial to a tennis bracelet on the opposing arm, and layered diamond necklaces from Henri Noel.
Classic bag
You have some flexibility in purse selection for this look, but I would stick with a classic silhouette if you can manage.
Goyard tote bag, Celine Triomphe, or Hermes Picotin are great silhouettes depending on the number of items you need for the day. I love a spring inspired tone here - robins egg blue or sage-mint green.
Hot take
I don’t trust when people are stylish but have badly designed homes, or vice versa. I think it’s morally incongruous to claim you care about aesthetic value but to put absolutely no effort into the design of your home. If you care about style then you should care about style. Plus, feeling put together in your space helps you breathe in the same way that putting on a good outfit does. If this offends you, maybe this is a sign to hire me as your interior designer?
Continuing the convo on No. 5
One item that is oft overlooked in registry creation is the value of having items that celebrate an important time in your life. The cash value you get for your wedding won’t necessarily make a dent in your down payment (if you live on one of the coasts in particular), but when else will you have the opportunity to spend a huge sum, guilt free, on beautiful things? We had some friends who thought our registry was outlandish and insane, and you know what? We got almost everything on it, and feel joy thinking every time we use one of the items we received when we think about the person who sent it. One can’t really do that with a pile of cash!
Lots of love xoxo
Ellie