The secret to pulling off a baseball cap in midlife

Suddenly this summer I started craving a baseball cap. Blame Challengers. Blame tennis core becoming a thing. Blame the unpredictable and rain-washed summer of 2024 and the very real question of how to keep one’s head dry…

I tell you this with both surprise and trepidation, because the last time I actively wanted a baseball cap I was listening to a Radio 1 Roadshow in Happy Valley Gardens, Llandudno when I begged my Mum to buy me a jazzy souvenir number. In the years since that heady 1970s summer, I’ve generally reviled the style: The slogans. The cringey incongruity of wearing an American sportswear icon with quotidian Brit attire (the millinery equivalent of the charity tee worn over a business shirt)... And let’s not get into MAGA hats.

But something has changed. Baseball caps have been elevated from sportswear uniform/random-merch-from-a-corporate-gift-bag to fashion status. At the Paris collections, I noticed attendees pairing tonal baseball caps with their voluminous trenches and kitten heels, Jodie Comer wore a “Ladies First” cap with a suit and bralet on her latest cover shoot for British Elle. And then Margot Robbie debuted her post-Barbie streetwear style looking impossibly cool in clotted cream-coloured oversized suiting, loafers and a New York Yankees beige women’s baseball cap. 

Of course, celebrities have long donned caps with their exercise get-ups (see Victoria Beckham in head-to-toe black gym attire), or for running errands around town in off-duty mufti. “It’s suddenly become a popular trend for everyone to wear,” says creative director and brand consultant Nicola Rose, who remarks that she recently noticed all the Chelsea girls milling around Duke of York Square off the Kings Road wearing a new uniform of throw-it-on sweatshirts, jeans and baseball caps (favouring labels like Varley, Frame, Alex Eagle Sports Club and Sporty & Rich, that deliver that sports luxe edge). “It’s all about taking those sports pieces that you might wear to the gym and making them fashion forward… It’s elevated, it’s got a luxe factor to it…”

I catch up with Alex Eagle, the powerhouse behind the eponymous sports luxe brand (among many other creative enterprises), who tells me that she is in fact wearing a baseball cap to do the school run, as we talk over the phone “I think we got really used to a kind of sporty, relaxed aesthetic during – and after – Covid,” she says. 

“And I think as you get older, wearing trainers and baseball caps helps give your outfit a little bit of edge. Now we are returning to a little bit more sophisticated glamorous dressing... I think a cap - a little bit like trainers – just gives a little bit of a masculine sporty attitude.”

Eagle continues: “I also think we’re so conscious of our skin...I’ve had lasers, so I’m under strict orders to wear factor 50 and wear a cap, and actually, the more you wear a cap, the more you get naked without one…They’re practical and functional, they cover a bad hair day, protect your skin, and it’s a fun way to wear something sporty, whether you’re wearing jeans and a T shirt or even, a blazer or a suit.”

The trend for injecting a bit of sports luxe into everyday wardrobes is not the only underlying force nudging us towards baseball caps. There’s also been a rise in popularity of easy nonchalant unisex pieces that bestow laidback cool, whoever is wearing them. Pip Durell, founder of shirt brand With Nothing Underneath, who taps into just this vibe with her coveted shirting, tells me that the label’s WNU logo cap has gained a cult following: 

“We made them with our core customer in mind. She’s laid back and cool, she wants a baseball cap to wear to work with a blazer but also with her gym kit at the weekend. Florence Pugh wore hers leaving dinner at Chateau Marmont during Oscar season, it was such a moment.”

“What we didn’t expect was this love from the men! We see so many men buying them from us, or taking their girlfriend’s. Nicholas Galitzine wore one at the Grand Prix and sales soared. It’s so nice, we love the nonchalance of the shared wardrobe and after all – we were built on borrowing from the boys so perhaps it’s time we lent them some back.”

And then there is the stealth wealth factor – the luxe baseball cap worn as the signifier of a curtain kind of HNW nonchalance. Think: Kendal Roy in Succession wearing his Loro Piana baseball cap in the Waystar boardroom. The uptown baseball cap is a look with a fine pedigree. Picture that epitome of Upper East Side minimalist chic Carolyn Bessette Kenendy striding out in her layered monochrome casuals, plus a classic navy baseball cap worn backwards (a style affectation also favoured by her beau JFK Jr). Modern discreet chic brands such as Khaite, The Row and Toteme all offer a nice line in tastefully neutral baseball caps in fabulously luxe fabrications (the Row’s cashmere ‘Caspian’ baseball cap is a cool £640 at My Theresa), while Toteme has a wool and cashmere baseball cap in camel for a mere £200 (also at My Theresa). 

If you are thinking woollen baseball caps sound like a bit of an oddity, it so happens that the original American baseball caps from the mid 1900s were originally made from wool (with a leather bill). It wasn’t until relatively recently that the standard cap worn by actual baseball players moved from wool to lightweight polyester. 

Away from the baseball diamond, you can buy a posh breathable baseball cap that can be worn all year round at Lock & Co (the world’s oldest hat shop in Mayfair). Infact, their Scout baseball cap is crafted in a fabric with UV40 SPF protection. “We sell loads to ladies actually,” says Maxwell Newman, assistant manager at the store. Not all customers approve, however. “They think of a baseball cap as being something incredibly modern,” continues Newman. “They come in for a flat cap and they’re horrified to notice the baseball caps are there…. I mean, they’ve been around since the 1800s, so I have to remind some people that they’re not as contemporary as they might think.”

So how to wear a baseball cap and look chic and modern? With the help of Telegraph stylist Sophie Tobin, I set myself the challenge of putting together three baseball cap looks: A grown-up preppy outfit for the weekend; a more dressed-up, tailored look that I could wear for a lunch on a restaurant terrace, say; and lastly…a baseball cap with dress (the goal here being to make it look chic and intentional, and not “I pulled this old thing out of the cupboard as a bit of emergency sun protection’’).

For the preppy look, we take inspiration from the world of Miu Miu, by layering stripes (a sharp boyish shirt over a breton tee; turn up the shirt cuffs to create a more flattering silhouette). I love the Bobbie’s kitten heels I’m wearing in these pictures, but the outfit would also work with a track-heeled fisherman’s sandal or trainers. I reach for a faded blue WNU baseball cap to add the finishing touch, but with her stylist’s eye Sophie advises a pop of red. She’s right, it’s an instant elevator and a more sporty, confident look.

Washed cotton cap, £32, With Nothing Underneath; Cotton shirt, £165, ME+EM; Organic cotton long sleeve tee, £32, Lucy & Yak; Wide leg jeans, £99, Mint Velvet; Leather shoes, £200, Bobbies x Juny Breeze

Next up, the girl-about-town outfit – a gorgeous, cream Me+Em tweed boucle bomber with white palazzo trousers and cool Aeyde mules. Sophie suggests a navy collegiate baseball cap to add a punchy exclamation point. “You look like a really chic American soccer mum,” she says approvingly. Just as before, adding a cap injects a bit of peppy attitude and makes me feel younger.

Norse Projects Twill cap, £85, Fenwick; Tweed jacket, £350 and cotton viscose trousers, £195, ME+EM; Leather shoes, £320, Aeyde; T-shirt, Sarah’s own; Gold plated earrings, £350, YSSO 

And so to challenge no. 3: The dress. “I think a baseball cap can work with a dress. I just think it needs to be understated utility. So it’s got to have this kind of sporty, effortless style,” advises Nicola Rose. What I want to find is the high street’s answer to an Hermes knit polo dress… and the cream and black crochet shirt dress you see in the photos, is a happy discovery from John Lewis. It’s a fun, easy shape to wear, perfect for a day at Wimbledon in fact. And pairing it with a Ganni baseball cap gives it a sassy, youthful edge; so much cooler than wearing it with a straw hat or a granny-ish crochet bucket hat. I am sold.

Organic cotton cap, £85, Ganni; Crochet dress, currently unavailable, John Lewis; Leather sandals, £195, Grenson; Gold vermeil earrings, £150, Monica Vinader

I consult Alex Eagle once more on her thoughts about dresses worn with baseball caps.

“Definitely! In the summer, if you’re wearing even a bias-cut, silky dress, I actually like it with trainers rather than sandals. A baseball cap rather than a straw hat, it’s just a cooler silhouette. It stops it feeling twee and brings it back to something a little bit more tomboy and cool, which is always the Ying to the Yang that I’m looking for with an outfit.” 

Styling lessons to live by indeed. Go on, put a cap on it!

How to wear a grown-up baseball cap with style

• When choosing the right, flattering cap for you – experiment with the height of the crown, and avoid choosing one that’s too tall or too square. (It’s a matter for debate, of course, but I’m not sure a trucker hat looks great on anyone over 35).
• Also think about the length of the bill – too long and you might risk looking like a cartoon character.
• As for colour? If you do fall for the grown-up baseball cap trend, I’d advise investing in a couple – a grown-up neutral (camel, cream, or grey) for wearing with your suits and tailoring and choosing something a bit poppier for when your weekend/outdoor festival outfit needs a pop. Black may seem like a no-brainer, but for someone with fair colouring like mine, it’s much too harsh.
• You can afford to go a little lighter and softer with your make-up to keep the look sporty, not too overdone.
• And experiment with how you wear your hair. If you are wearing a ponytail, a few strands to frame your face can look very pretty. Wearing your hair down? Tucked behind the ears generally looks more grown-up, less Wayne’s World!