Skip to main contentSkip to footer
Digital Cover culture

Chic Critique: Why you should skip the baker boy hat - unless you're Paris Hilton

Baker boy hats are making a comeback, but H! Fashion's Tania Leslau says they are a one-way ticket to being pigeonholed

When you purchase through links on our site, we may earn commission. Read our full commerce guidelines here.

Tania Leslau
Fashion features writer
October 27, 2024
Share this:

As much as I want to, I can’t get behind baker boy hats. Don’t get me wrong, I love headwear and think it’s highly underrated. Yet, there’s something about the gently puffed, stiff brimmed caps that seem try-hard, perhaps because their popularity has waxed and waned throughout the years.

Unfortunately for those who feel the same, baker boy hats are very much back on the British sartorial agenda. Lily James and Zoe Saldana have already championed the design this season, asserting the accessory as one to watch for AW24.

My issue with the hats is that they are so easy to get wrong. Opt for an overly voluminous rendition and you look like Toad from the Super Mario franchise. Decide upon a flatter version and you’ll automatically channel East End gangster à la Guy Ritchie. Or Oliver Twist for that matter. If this is what you were going for, then we recommend a grey plaid print. 

Paris Hilton © Getty
Paris Hilton
Britney Spears© Getty
Britney Spears
Jennifer Lopez © Getty
Jennifer Lopez
Christina Aguilera© Getty
Christina Aguilera

Their hybrid nature is hard to chew on. The baker boy hat, also known as a newsboy cap or flat cap, has its origins in 19th-century Europe, particularly in Britain and Ireland. Initially worn by working-class men, especially young newspaper sellers (hence the name ‘newsboy cap’), dockworkers, and bakers, it became a practical, affordable headgear.

By the early 20th century, the style gained popularity across different social classes, including the aristocracy, thanks to its association with rural leisure activities like hunting and driving. 

Love Actually© Love Actually
Love Actually, 2003

In the 1960s and 1970s, the baker boy hat saw a resurgence in fashion, worn by celebrities like The Beatles. Its vintage, casual appeal continues to make it a popular fashion statement today, offering a blend of practicality and style that harkens back to its working-class roots.

Then, the Noughties hit. Jennifer Lopez, Britney Spears, Christina Aguilera and perhaps most famously Paris Hilton embraced baker boy brilliance, pairing the hat with low-slung, bootcut jeans, butterfly tops and Y2K accessories. Not to mention Keira Knightly’s black variation in Love Actually (solely worn to cover a break out, FYI.)

Penelope Cruz in chanel © Getty
Penelope Cruz
David Beckham in baker boy hat© Getty
David Beckham
Bella Hadid© Getty
Bella Hadid

The hat’s early Aughts connotations are what helped the piece to resonate with Gen Z today, who tend to covet all-things Y2K. 

Which is why, like so many other trends spanning cargo pants to camo print, it’s now overdone. Baker boy hats have turned into an ironic statement, often worn by twenty-somethings trying to bring back the early 2000s in today's fashion - much to the chagrin of millennials. And don’t get me started on the tweed editions that shriek inheritance-chic with a signet ring. Tweed scrunchies would be so much cuter.

If they bring you confidence, then by all means do away with my opinion and wear the hat. For trend followers out there, before the silhouette comes bounding back on social media feeds and high streets alike, I urge you to consider other, more timeless options that aren’t a weird Y2K-working class cosplay. Personally, I await the day the humble cloche returns.  

Fashion is of course about having fun, but it’s also about individuality. The baker boy has been done time and time again. Isn’t it time for something new?

How to wear a baker boy hat:

bella hadid in baker boy cap© Getty
With a pop of silver to modernise the look
chanel outfit © Getty
With a designer brooch to draw the eye
kate moss in green trousers© Getty
With a utilitarian-chic twist
With wide leg jeans and a structured coat© Getty
With wide leg jeans and a structured coat

How I would style a baker boy hat:

  • BLAZER: Remain Denim Blazer, £272, FARFETCH
  • HAT: Women's Blue Denim Hat, £550, PRADA
  • JEANS: Straight Foil Jeans, £59.99, MANGO
  • SHOES: Denim Pointed Slingback Kitten Heels, £135, COS

HELLO!'s selection is editorial and independently chosen – we only feature items our editors love and approve of. HELLO! may collect a share of sales or other compensation from the links on this page. To find out more visit our FAQ page.

Sign up to HELLO! Fashion for style tips, cultural insights, must-have items, and more

By entering your details, you are agreeing to HELLO! Magazine User Data Protection Policy. You can unsubscribe at any time. For more information, please click here.

More Culture

See more