34 Iconic Starlets Guaranteed to Inspire Your Classic Fall Style

Classic style conjures up visions of timeless wardrobe staples — the crisp white button-down, a wide-legged trouser, camel coats, skinny jeans, leather midcalf boots, and ballet flats — and the kind of styling approach that's polished and never fussy. Certain women know exactly how to nail this Fall outfit equation every single time, whether it be with a masterful display of layers, an eye for tailoring, or a covet-worthy collection of boots. We're looking at you, Gwyneth Paltrow.

But before Gwyneth, and before the trench coat stylings of Alexa Chung and Kate Moss, the very beginnings of great cold-weather fashion can be traced back to the likes of Audrey Hepburn, Jackie Kennedy Onassis, Ali MacGraw, and an effortlessly cool Francoise Hardy (pictured). To add to the growing list, we've also got modern-day starlets Angelina Jolie, Kate Middleton, and Kate Bosworth to take cues from as the seasons change. Trends come and go, but these women show us how to capture timeless beauty with no-fail minimalism.

Ali MacGraw
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Ali MacGraw

In 1970, Ali MacGraw epitomized effortless chic in Love Story.

Angelina Jolie
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Angelina Jolie

We love Angelina's take on classic creamy tones — the pumps, the bag, the coat, and the sheath all speak to understated sophistication.

Faye Dunaway
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Faye Dunaway

When we think of iconic early '70s style, we instantly think of a very chic Faye Dunaway — scarves, knits, and long, lean trousers à la Bonnie and Clyde.

Emmanuelle Alt
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Emmanuelle Alt

It's hard to ever find fault with French Vogue's editor in chief, Emmanuelle Alt. While she rarely deviates from tailored blazers, black jeans, and low heels, we love that, here, she employed the use of stripes to keep the look dynamic.

Audrey Hepburn
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Audrey Hepburn

Turtleneck? Skinnies? Loafers? Check, check, and check. Audrey Hepburn hits all the right Fall fashion notes in Funny Face.

Alexa Chung
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Alexa Chung

Alexa is notable for mixing the classics with her own signature style elements — this time in a fuzzy white topper, slick leather miniskirt, ankle boots, and a heart-print Burberry Prorsum clutch — for modern polish.

Gwyneth Paltrow
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Gwyneth Paltrow

Gwyneth used flashes of white — found on her sunglasses and on the soles of her Stella McCartney boots — to offset her chic black outfit.

Kate Middleton
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Kate Middleton

Kate has a way with elegance, choosing classic pieces in figure-flattering silhouettes — even if it's just a svelte pair of dark denim, Wellies, and Fall-hued layers to get the look.

Katharine Hepburn
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Katharine Hepburn

The iconic actress set a new standard for feminine elegance, adopting chic wide-legged trousers and menswear as her own in 1954.

Katie Holmes
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Katie Holmes

Katie is a girl after our own denim-loving heart. She consistently styles up the most-classic Americana staples. Case in point: this denim skirt look made even cooler with burgundy boots and a gray fedora.

Reese Witherspoon
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Reese Witherspoon

Reese sticks to feminine classics, opting for perennial favorites, like a breezy printed skirt paired with a soft oversize sweater and suede knee-highs.

Anne Bancroft
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Anne Bancroft

Glamorous but never overwrought, Anne Bancroft gave us inspirational glamour in The Graduate. Kate Middleton might have ushered in a modern era of nude hose, but Anne made us fall in love with black first.

Jean Seberg
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Jean Seberg

Jean Seberg's chic, understated style in In the French Style is perfect portrait of the Parisian look so often sought after.

Clémence Poésy
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Clémence Poésy

We're totally smitten with her effortlessly Parisian-cool take on classics. This polka-dot top combined with textured trousers gets a sophisticated upgrade but remains a perfect everyday outfit.

Kate Moss
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Kate Moss

The queen of boho cool still pays homage to the classics with the most-luxe counterparts: a gorgeous fur coat, cozy jersey layers, and slouchy tall boots.

Cameron Diaz
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Cameron Diaz

Cameron sticks to a low-key classic style MO in a stellar mix of skinny jeans, sleek ankle boots, soft sweaters, and tailored blazers.

Jennifer Aniston
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Jennifer Aniston

With style that's both sexy and approachable, Jen mixes up more menswear-inspired pieces (like a schoolboy blazer and boyfriend jeans) with ankle boots and a cute black bag.

Candice Bergen
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Candice Bergen

Candice epitomizes chic, sensible style, snapped here in 1970.

Sarah Jessica Parker
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Sarah Jessica Parker

We could wax poetic about Sarah Jessica Parker's ultraladylike style year-round, but today, we pause to admire just how genius this long-sleeved plaid swing dress and peep-toe booties were for a Fall evening on the town.

Jackie Kennedy Onassis
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Jackie Kennedy Onassis

Jackie Kennedy Onassis forever popularized oversize shades, pearls, flats, and the understated appeal of classic dressing.

Rachel Bilson
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Rachel Bilson

We'll leave the playful prints (in a darker hue) and exotic textures (a great leopard pattern never goes unnoticed) to Rachel Bilson, who always excels at putting a youthful spin on classic pieces.

Olivia Palermo
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Olivia Palermo

Admittedly the most eclectic of the bunch, Olivia offers the most risk-taking styling approach to the most classic of autumnal wares. Take this leather-on-leather look — she injected an edgier mood with studded accents found on her jacket and sunglasses. The best part about classic Fall style is how it can morph into a plethora of unexpected sensibilities.

Miranda Kerr
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Miranda Kerr

Miranda Kerr dressed up an all-black outfit with surprisingly cool elements — black-and-white oxfords, retro round sunglasses, and a luxe fur coat.

Jessica Alba
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Jessica Alba

Jessica Alba opted to punch up this classic layered ensemble with complementary tones of blue and purple. And can we talk about those gorgeous boots?

Elizabeth Olsen
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Elizabeth Olsen

The paisley-print top put a fresh spin on Elizabeth Olsen's monochromatic ensemble.

Natalie Portman
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Natalie Portman

Look to Natalie's wear-with-everything trench coat and sophisticated bow pumps for easy work-wardrobe solutions.

Emma Stone
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Emma Stone

Emma Stone's tartan plaid jacket and ballet flats provided a double dose of off-duty-meets-classic appeal.

Rachel Zoe
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Rachel Zoe

Rachel Zoe sticks to her go-to wide-legged silhouette, but we love the white blouse and printed blazer addition.

Francoise Hardy
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Francoise Hardy

The French actress and singer possesses that cool-girl style that only comes naturally to a select few. But we'll try our darnedest to play copycat, starting with the most-tangible pieces in her wardrobe: the perfect trench coat and boxy sunglasses.

Brigitte Bardot
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Brigitte Bardot

A sweet headscarf and statement bag can dress up the most basic of trench coats; just look to siren Brigitte Bardot for extra inspiration.

Eva Mendes
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Eva Mendes

Eva puts her bombshell spin on classic Fall hues — try floral-print trousers with lug-soled boots and a brightly colored coat for a similar brand of cool.

Blake Lively
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Blake Lively

Blake's penchant for classic silhouettes with a quirky twist is most evident here. Houndstooth print and textured stripes made it cozy and cute!

Zoe Saldana
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Zoe Saldana

Zoe's take on menswear-inspired outerwear paired with slim-fit jeans and sleek boots made this look a timeless one.

Kate Bosworth
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Kate Bosworth

Kate gravitates toward simplistic layers topped off by statement outerwear and standout accessories. Case in point: a cool saffron-hued jacket, textured booties, and sleek aviators.