Sure, her Breakfast At Tiffany's look might be the most recognizable, but no ensemble has inspired such a relaxed revolution as Audrey Hepburn's revival of the ballet flat. Thanks to both Funny Face and Sabrina, the starlet created an ankle sensation, taking the long-forgotten flat and giving it a chic revival with the slimming black pant. (The exposed leg adds a cheeky wink to the all-black ensemble.) Today, the ballet/fitted-capri combo is just as smart and dapper as ever.
Diane Keaton & Menswear
Today, anytime we see a woman wearing slouchy slacks, a loose button-up, and a bowler hat, we can't help but equate her to Annie Hall. While Annie as a character had spot-on style inspired by the typically masculine, all of the clothes in the movie came from Diane Keaton's actual closet. Thanks to Keaton, low-slung belts, lapels, and collared shirts suddenly became the stand-in for effortless cool.
Courtney Love & Babydoll Dresses
Before Courtney Love, babydoll dresses were for, well, babies and dolls. Actually, their popularity crested during the late '60s, but the alternative music scene of the late '80s and early '90s latched on to them in an a way that was both ironic and genuine. Playing with and upturning preconceived notions of femininity, alt fans and groups wore the babydoll while moshing, sweating, and screaming their way through concerts — things Courtney Love excelled at. For a moment there, she was queen of the alts and her royal garb was, iconically, the babydoll.
Gwen Stefani & White Muscle Tees
Hey, remember when sleeveless T-shirts were for aerobics classes and plumbers only? Yeah, we can barely recall either. See, since No Doubt crashed through the top of charts with "Don't Speak" 18 years ago (yes, 18 years), it's become perfectly normal for an otherwise luxe-dressed young lady to rock a ribbed tank or other sporty tops along with her statement accessories (questionably appropriate bindis included). Hey, our managing editor has about 20 of them. And, yes, even though she's gone on to much frillier fashions with L.A.M.B., whenever we see a fit female in a white top with her belly and arms exposed, we're always going to think of Gwen Stefani...or aerobics.
Sarah Jessica Parker & Manolo Stilettos
Yep, Manolos! From the 1970s all the way up to the turn of the century, the arching, dead-sexy stilettos created by the Spanish designer were, indeed, the toast of the Upper East Side, Monaco, and anywhere else money and high style flowed. But it was only when Sarah Jessica Parker's Sex And The City character fell into ecstatic fits over them that these works of footwear art — once primarily familiar to Vogue readers and the Bergdorf-set — became mainstream fetish objects. Now "Manolo" is a byword for sexy, flashy, often outré femme style, tied forever to the woman also known as Carrie Bradshaw.
Kate Moss & The Leopard Coat
Yes, yes — the leopard print is, quite literally, prehistoric. But, honestly, toward the end of the 20th century, coats made out of the print were more associated with senior citizens and rich women of questionable taste. The secondhand stores were filled with them. But then Ms. Moss slipped on your grandma's old leopard-print coat, and it became dangerous, deadly, and decidedly young again. Also, given how much she wears them, we kind of feel that if leopard-print looks hadn't already existed for centuries, Kate Moss would have had to invent them. That or go naked half the time.
Mary-Kate/Ashley Olsen & Hobo-Style Boho
The tabloid press used to call them "bag ladies," and for a moment there, we were right along with them. But then we warmed to this luxe, oversized take on the old-boho style, realizing that these young ladies were playing with their physical size and financial might in a particularly fashionable, amusing way. Suddenly, we looked around, and everyone's coats were scraping the pavement...even ours. To this day, whenever one of our staffers saunters into the office with hangover-blocking shades on, a two-sizes-too-big cardi, and a Venti latte, we say, "Good morning, MK!"
Nicole Richie & The McQueen Scarf
Perhaps no one in our little circle of beloved fashion notables has risen so high from starting so low as Nicole Richie. Let's remember it wasn't all that long ago that she was wearing Wet Seal looks and palling around with Paris Hilton. But then the lady went boho — and we're not talking just any kind of boho. No, her casual pieces — from torn jeans to hippie dresses to her ever-present scarves — are always impeccably sourced. It's become a sort of dreamy, intelligently flung-together Cali style that has turned her into a serious fashion commodity, and the rock-'n'-roll scarf is the linchpin.
Alexa Chung & The Peter Pan Collar
Dating back to at least the Renaissance — centuries before J. M. Barrie was even born — the Peter Pan collar has been favored by the fashionably demure. Somehow, though, none of the many chic women who've worn it over the centuries have ever owned it like Alexa Chung has. For someone so brash and bold, somehow the collar makes her simultaneously more girlish and more laddish — a neat trick. She even uses them to add a wink to even the most dramatic dresses — so much so that it's hard to imagine her neck without one.
Jenna Lyons & Daytime Sequins
Fittingly, the maven of J.Crew is also the harbinger of well-heeled daytime glam, or the pairing of opposites, if you will. Boyfriend jeans with heels, button-ups on the red carpet, and toning down sequins for a bit of sunlight-ready flair. Thanks to Lyons' lead, we've got a new paragon of effortless, comfortable style.
Rihanna & The Flat-Brimmed Hat
Her hair seems to change by the hour, but the hat remains the same. Rihanna looks good in just about everything she wears, be it haute couture or simple street wear. But her strongest sartorial connect to her hip-hop roots, however, remains her flat-brimmed, always-sharp lids. More to the point, as her look becomes more and more refined and feminine, the hats point to her boyish charm (and make us want to invest in our own). Honestly, if we went a week without seeing her in one while stepping off a tour plane or into a club, we would start to worry about her.
Want to see more from the Stars? Click through to check out Carrie Underwood and others in the Hits and Misses from the Academy of Country Music Awards!
Jewel looked like a gem in this sparkly peach gown.
Between the hair (on both!), the bedazzled leather jacket and the cleavage overload, this duo made our "Miss List."
We're really not quite sure what's happening with this dress or those overalls, but we know we're not a fan!
We love a good peplum, and this silver gown looked gorgeous on singer Maggie Rose.
We have to say RaeLynn's hair looks amazing (though we'd remove that big flower) -- but her outfit is just too over the top for our taste.
Hillary Scott, mom-to-be, looked gorgeous (and glowing!) in this navy gown, and her bandmates Dave Haywood and Charles Kelley were absolutely dapper!
The dress itself is fairly plain, but we just can't get past Jaida's hair!
Scotty looked quite sharp, and we LOVE the gingham tie! (Plus, any man who know to pair navy with brown is a winner in our books.)
Sometimes feathers are too much, but not in this case! Singer Kacey Musgraves nails it in this fun and flirty dress.
Walker's jacket is cringe-worthy enough, but then we noticed how short Craig's dress is. Not our favorite looks!
We're not sure we've ever seen a dress made in the color of that skirt before, and we don't think it's a trend that'll be catching on ANY time soon. From head to toe, this one's a miss!
Kramer was dazzling in this embellished gold gown.
We could do without the black lace peplum on this dress, if you could call the very flat fabric a peplum!
Luke Brian, co-host of the show with Blake Shelton, chose a very nice jacket over dark slacks, while Caroline Boyer glowed in a backless metallic dress.
We'd change the hair for sure, but we're loving this BCBG dress on Kaley!
Shania, what were you thinking? This dress with what looks like coattails behind it is already not our favorite, but to pair it with these boots(especially in springtime) just feels wrong!
Actress Beth Behrs looked pretty in pink, wearing a lace gown.
We LOVE Faith, but felt the slit on the front of this lace Chado Ralph Rucci dress went a bit too high - so we'll have to call this outfit a miss.
Stafford rocked this wrap-like emerald gown like a pro, and looked stunning!
The "Blown Away" singer looked lovely in this floral gown.
Danielle Peck certainly took a risk with this dress, but it's a miss for us.
There's some big hair going on for these siblings, but all three looked great.
We don't love the sheer shawl Shawna is wearing over her shoulders, and were glad to see it could be removed when she and her husband accepted their award!
There's too much pattern going on here for our liking -- we prefer a classic suit. But we must say it looks tailored for him perfectly!
Taylor never seems to let us down, and the ACM Awards were no different! The singer looked glamorous in a metallic embellished gown.
We know Casadee has a bombshell voice, we just wish she'd picked a bombshell dress!
We'd like this look better if Tori pulled her hair into a fun updo and added some glam with a great pair of earrings.
Jones looked stunning in this simple one-shouldered gown.
How amazing does Sheryl Crow look? We love that she went with this daring outfit -- and we think she pulls it off perfectly.
We don't know about you, but we were afraid that this dress was a wardrobe disaster waiting to happen for Ms. Lambert!
Hayes looked quite sharp in this outfit, keeping it comfortable by choosing a pair of sneakers over dress shoes.
O'Dell looked lovely in this flowing white and gold gown.
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Most things that spawn from celebrities aren't always so pretty: Lady Gaga's heelless shoes, Ke$ha's blue lipstick, and even a certain socialite's penchant for putting her chihuahua in her purse. Yet, every now and again, a tastemaker comes along and really ignites a craze, inspiring a whole group to follow in his or her stead.
Sure, they may have had their fingers on a sort of pulse or caught a glimpse of something cool in the fashion crystal ball, but each of these looks didn't really take off until one of these women truly made it her own. Fortunately, it's good to know that not every style-star trend involves putting a pooch in a bag.