I Dressed Like My Favorite Style Icons to Get Out of My Fashion Funk

Welcome to I Tried It Month, where we’ll be publishing a new fashion, beauty, or wellness article every day in January that features a first-person account of shaking up an old habit, pushing beyond a comfort zone, or simply trying something new. Follow along for 31 days of storytelling, including everything from going without a cellphone for 40 days to trying the polarizing low-rise pants trend. 

I think I've established here clear enough that I have an avid love for pop-culture. Whether it's the latest music trend to blow up on TikTok (Have you listened to 'Drivers License' by Olivia Rodrigo yet? If not, please do) or the hit TV show that everyone is watching (Hi, Bridgerton), I like to keep tabs on it all. Some may say I have issues, I like to think it's a hidden talent. What many may not know is that my love of pop-culture also stems from my love of fashion, because it's no secret that there's a variety of stars and fictional characters that bring on the style game that people remember forever. 

In high school, I loved saving scenes from my favorite shows and movies to recreate their looks to wear. Since 2020 has left me still in quite a bit of a fashion slump, I thought I'd go back to my roots and mimic outfits from different style icons with what I already own in my wardrobe. It can be easy to fall into a routine of wearing similar items and feeling the pressure to follow every trend on the market, so playing with different characters' style definitely helped me remember what I loved about clothes in the first place, which is wearing things that simply spark joy.

Cher Horowitz

Sweater vests may be a trend you see worn commonly today, but it was in the early 2000s where Cher Horowtizs dominated the scene. Her preppy yet forward style is one of my all-time favorites, so I had to do a little vest over collared shirt action in her honor.

When I think of Hilary Banks I think of luxe fabrics, gold jewelry, and boxy retro blazers, so that's exactly what I pulled out to mimic her style. I've had this vintage YSL blazer for years and it completed the look.

Rachel Green

There are two things from Rachel Green's wardrobe that have always stuck with me—blazers and overalls. I've had this pair of overalls sitting in the back of my closet for some time, so this was the perfect outfit to pull it out for. 

Princess Diana

I'd be lying if I said I didn't buy this sweater right after watching The Crown on Netflix. Princess Diana's sweater collection is one to marvel at, and the costume designers of the show replicated every one of her iconic looks perfectly.

Fun fact: I owned Lizzie McGuire flip-flops that I wore with almost every single outfit in middle school. From the small peaks we got at adult Lizzie before the reboot was canceled, I'm sure she'd still be all about pattern mixing and flared jeans in 2021.

P.S., Now through 1/31, get 25% off dresses at Lisa Says Gah by signing up for The List, Who What Wear's free membership program that includes exclusive discount codes and other perks.

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