Karen Solomon 10/13/25 Karen Solomon 10/13/25

Diane Keaton Style

How to get Diane Keaton’s menswear inspired fashion

It’s not for nothing that Diane Keaton is known as much for her style as she is for her illustrious acting career. She pioneered menswear for women and had a flair all her own. Her signature hats and gloves on the red carpet also served a purpose. She had been diagnosed with skin cancer at the age of 21 and thus found a chic way of covering up that became her signature. And though Annie Hall is often credited with her style, Diane used her own wardrobe to dress her character, much of it thrifted from Goodwill.

Anne Fontaine white bow blouse — ANNE FONTAINE white bow blouse or MISTOOK tie neck poplin shirt

Gigi Burris wool black beret — GIGI BURRIS Mia wool beret or this PRETTY LITTLE THING knit beret

Simon Miller striped black and white poplin button up shirt — SIMON MILLER poplin button up or this LANDS’ END no iron shirt

Reformation vest and wide leg pant set — REFORMATION Taryn Two-Piece

Manolo Blahnik button black and white pumps — MANOLO BLAHNIK Sisygambis pumps

Me + Em pinstriped suit — ME + EM Evening suit

L'Agence patent leather black and white loafer — L’AGENCE Maelys patent leather loafer or these NATURALIZER Sheila loafers

J.Crew women's cashmere vest — J.CREW Cashmere relaxed sweater vest

M.M.Lafleur black leather gloves — M.M. LAFLEUR leather gloves (half price!)

J.Crew Black oversized blazer coat — J.CREW Gamine Blazer-Coat

Banana Republic black loafer chelsea boot — BANANA REPUBLIC Penny Chelsea Boot

Look Optic Keaton glasses with blue lenses — LOOK OPTIC Keaton readers

Favorite Daughter natural pinstripe coat — FAVORITE DAUGHTER Meyer Coat (70% off!)

GAP oversized cotton white shirt — GAP organic cotton poplin big shirt

Brooks Brothers black tie with tiny white polka dots — BROOKS BROTHERS dot rep tie or MILLE Zoe necktie

Favorite Daughter cream blazer and pleated low pants — FAVORITE DAUGHTER the Favorite Blazer and FAVORITE DAUGHTER the Favorite Low Pant or

Ralph Lauren khaki pleated pants — RALPH LAUREN Wool blend Bacall pant or this ARITZIA Effortless Pant

B-Low The Belt ivory waist belt with gold buckle — B-LOW THE BELT Nolami leather waist belt or STREETS AHEAD Roger tan/gold waist belt

Lauren Ralph Lauren camel and white wingtip pumps — LAUREN RALPH LAUREN wingtip pumps

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