And Now, the Easy Way to Master Ashley Olsen's Style

For many of us, Ashley Olsen has been a style icon for decades. Beginning with her fashion moments from growing up in the spotlight as a young actress to her foray into fashion with her launch of The Row, her style evolution has been fascinating to watch. Her penchant for timeless and classic pieces can’t be denied, but she also gravitates toward vintage items that make a statement. There’s no denying her seriously chic style, so we’ve rounded up Ashley Olsen’s best style moments of all time. Inspiration from the iconic fashion girl ahead.


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Can flip-flops look chic? Ashley Olsen wore the ultimate casual shoes with some of her signature pieces: a loose maxi, an oversize tote, and sunglasses. Follow no need to invest in designer sandals for summer when you can wear Olsen-approved flip-flops, right? 


(Image credit: Getty Images)

Ashley creates a chic and laid-back look by pairing her comfortable turtleneck with black leggings and a long wool coat.


(Image credit: Getty Images)

Take a hint from the actress and wear your cozy sweater over a silk dress.


(Image credit: Getty Images)

For a more dressed-up and elegant look, Ashley opts for a long billowy dress.


(Image credit: Getty Images)

Going for a more tailored look, Ashley rocks a suit dress with simple jewelry and minimalistic hair.


(Image credit: Getty Images)

For a simple, chic look, Ashley tucks a plain white tee into a belted skirt with suede mules.


(Image credit: AKM GSI)

Mastering her cool airport style, Olson pairs simple skinny black jeans with a long tee, an oversize coat, and loafers.


(Image credit: AKM GSI)

For a more put-together ensemble, she takes the same formula as the previous look but pairs the pieces with kitten heels and a classic white turtleneck.


(Image credit: Getty Images)

A simple slip dress is the ’90s-throwback look endorsed by Olsen.


(Image credit: Getty Images)

She proves that you can never go wrong with classic pieces like a camel coat and slingback heels.


(Image credit: Getty Images)

She dresses up all black with a blue croc bag.

Don’t be surprised if you see us copying all of these looks.

Associate Director, Special Projects

Kristen Nichols is the Associate Director, Special Projects at Who What Wear with over a decade of experience in fashion, editorial, and publishing. She oversees luxury content and wedding features, and covers fashion within the luxury market, runway reporting, shopping features, trends, and interviews with leading industry experts. She also contributes to podcast recordings, social media, and branded content initiatives. Kristen has worked with brands including Prada, Chanel, MyTheresa, and Luisa Via Roma, and rising designers such as Refine and Tove, and her style has been featured in publications including, Vogue France, WWD, and the CFDA. Before Who What Wear, Kristen began her career at Rodarte, where she worked on assistant styling, photo shoots, and runway shows, and at Allure, where she moved into print and digital editorial. She graduated from the University of Southern California, where she studied art history and business, and currently lives in New York.