All that will be left to do is to don some rockin’ shoes – I recommend some classic Chelsea boots in leopard print. Throw those on with some Wayfarers (Debbie’s signature), mess your hair up with some dry shampoo, and you’ll be stage-ready and rocker chic just like Debbie.

Love Debbie’s look? Check out our guide to Debbie Harry style!

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14. Lucille Ball

A while back when I was watching I Love Lucy reruns, I was struck by how stylish Lucille Ball‘s clothes were. Who knew that show had such awesome fashion inspo? Along with being hilarious and beautiful, Lucille also manages to wear beautifully tailored pant suits, dresses, and heels that Blair Waldorf would lust after.

Shop Lucy’s Closet

Products:

• Dress – Macy’s
• Pearls – Amazon
• Lipstick – MAC “Russian Red”
• Shoes – Aldo

Where would I Love Lucy be without all those gorgeous dresses? The answer: nowhere. I love the dresses Lucille Ball wore on I Love Lucy, and to mimic her style, I found the most adorable plaid shirt dress. Pair the dress with a pair of oxford shoes (I love the modern detailing of these) and some pearls you’ll instantly feel ’50s-chic.

Do you love Lucy? Take a look at our guide to Lucille Ball’s style!

15. Katharine Hepburn

We owe a lot to Ms. Katharine Hepburn. By refusing to wear makeup and pushing boundaries by wearing pants on screen, she blazed a path for menswear-inspired looks for generations to come. But whether she was rocking a chic pantsuit, evening gown, or a peter pan collar blouse, she spoke her mind and was fearlessly herself – and if that’s not fashion icon material, I don’t know what that is.

Shop Katharine’s Closet

Products:

• Jeans – Everlane
• Belt – Madewell
• Shirt (similar) – Amazon
• Mules – Madewell

To start off my Katharine-inspired outfit, I pulled a cute pair of boyfriend jeans and paired them with this striped button-up. After that, I found a simple belt and some classic flat mules.