If there is one accessory that can truly make or break an outfit, it’s most certainly a hat. Used wisely, it can up the sophistication and fashionable forwardness of any ensemble. Used incorrectly, however, and you’ve got a certifiable style catastrophe on your hands. And Hollywood has definitely experienced both the peaks and valleys of hat style.
So as we celebrate National Hat Day today, we felt it was only right to pay homage to some of the best and some of the worst in celebrity hat styles over the years.
Photo: WENN/ Sidewalk
Over the years, Pamela Anderson has crafted many signature looks. From her time running in slow-motion on the beaches of “Baywatch” to her days embracing latex get-ups in “Barbwire,” Anderson is memorable in almost any costume she tries on. But one of our favorites: The outrageous, fluffy pink hat she wore out and about with then-hubby Tommy Lee when they attended the 1999 MTV Video Music Awards.
LL Cool J
Photo: Chris Connor/WENN
It’s Mr. Kangol himself, LL Cool J. While he certainly became more refined as the years went by, LL had some questionable fashion choices back in the day. Most notable among them was his trademark, ’90s Kangol hat that back in the day was fly, but upon further inspection today makes us a little uneasy. But we still love you, LL!
Words could probably never describe exactly what was going on with Princess Beatrice and her interesting selection for the royal wedding. And while we were left utterly confused, we have to give her props for one fearless hat selection.
Photo: Ivan Nikolov/WENN.com
Erykah Badu has always put an emphasis on what’s going on upstairs. From a stunning fro to the can’t-miss-her hat seen above, Badu has never been one to shy away from a bold style decision… and we kind of love that about her.
Now we’re not saying that Pharrell Williams hadn’t discovered hats until his epically successful “Happy,” but it sure seems that way sometimes, doesn’t it? Ever since he busted out with that catchy little ditty, we’ve been hard-pressed to find the man sans his Vivienne Westwood hats. Not sure we’ve lovingly embraced this look yet, though.
Lady Gaga has worn many memorable ensembles over the years. A style icon and a fashion trailblazer, we are mesmerized each time she hits the red carpet. And we probably weren’t any more amazed than when she showed up to the MTV VMAs in one of her most unique outfits of all: A meat dress and matching hat. Yummy?
Hugh Hefner and sailors hats are like Hugh Hefner and breasts. They’re pretty much inseparable. And even after all these years, we still kind of dig his style and swagger. Keep on keeping on, Hugh.
Nothing about Grace Jones has ever been subtle. And that has certainly extended to her choice of headpieces. Case in point: The stunning headdress she wore at the Wireless Festival held at Hyde Park in London.
We couldn’t put together a list of memorable celebrity hats without Bob Marley and his Rasta-inspired, knitted beanie being included. His look summed up a generation of fans and continues to inspire to this day.
We’re not afraid to admit it here: Madonna’s style game in recent years really has us scratching our heads. Back in the day she was a style trailblazer whose fun and fearless approach to clothes made us smile. Now, we’re not sure what it does to us. Just look at the pilgrim-y topper she wore to the 2014 Grammy Awards. Yup, not our favorite.
Lisa “Left-Eye” Lopes
In the early years of supergroup TLC, their style was as eclectic as the group members themselves. Particularly, rapper Lisa “Left-Eye” Lopes shone as quite a beacon of fun and funky style. One of our favorite pieces of her look: the oversized, slouchy hats she rocked.
Hana Mae Lee
Photo: Adriana M. Barraza/WENN.com
Well, this one was sure interesting. “Pitch Perfect” star Hana Mae Lee donned a crumpled cigarette hat to the 2013 MTV Movie Awards. This statement maker was odd, unexpected and not necessarily something we’d wear everyday (or ever to be quite honest). But we give Lee all the credit in the world for this bold selection.