When I think about iconic fashion moments in film, Clueless is one of the first things that comes to mind. From plaid skirts to tank tops under plain white t-shirts, Clueless set forth bold, preppy trends that would forever be in style.

Today I am so excited to share with you my Clueless inspired lookbook! I’ve told you all about my love for 90s fashion before, so this is something I’ve been wanting to do for as long as I can remember. I’ve been working on this lookbook for several days now, trying to make sure all the outfits and the photos were exactly how I imagined them, and I am pumped to finally be putting it together.

Similar to what I did with my Friends lookbook, I drew inspiration from some of my favorite outfits that Cher Horowitz wore in Clueless and put my own spin on them. The goal of this wasn’t necessarily to recreate the Clueless outfits, but to capture the essence of them without having to purchase anything new. Everything I am wearing here came straight from my closet. No trips to the store necessary.

I really love doing these types of posts. They’re a fun challenge, and they force me to think of creative new ways to put some of my old pieces to use. I really hope you enjoy my take on Clueless fashion, and if there’s anything else you’d be interested in seeing in the near future, please feel free to let me know!

Look #1: Black-and-white plaid

OUTFIT DETAILS:

BLAZER* (similar): Forever 21

BLOUSE* (similar): Forever 21

SKIRT* (similar): Alexander Wang

SOCKS* (similar): Kelly & Katie

SHOES* (similar): J. Renee

I couldn’t do a Clueless lookbook without including an outfit inspired by the film’s most iconic look. I am totally in love with the way this turned out. Not to mention, it was super easy to put together.

I got this black-and-white plaid blazer at the thrift store a few months ago for, like, only a couple of dollars. I see blazers similar to this at thrift stores all the time. While they at first may seem old and outdated, they can actually be really cute if you pair them with the right pieces (though I must warn you, you may have to cut out shoulder pads).

Anyway, I threw my plaid blazer over a cream colored blouse and high-waisted black skirt. To finish off the look, I added a pair of cream knee socks, decorative sunglasses, and ballet flats.

Simple and preppy, I feel like this look does a good job of taking Cher’s outfit and giving it a slightly different twist. Black-and-white ensembles are a staple of mine, so I can definitely see myself wearing this outfit now and in the future.

Look #2: Button-down skirt

OUTFIT DETAILS:

SWEATER* (similar): SheIn

SKIRT* (similar): Forever 21

SHOES* (similar): Crown Vintage

For look number two, I decided to take inspiration from an outfit Cher wore that I think is seriously underrated: the button-down skirt and long sleeve top. Button-down skirts have come back into popularity in the recent years (though I’m honestly not sure they ever left), so this seemed like a trendy look to try out for myself.

Here I am wearing an olive green corduroy skirt with a plain white-gray cropped sweater. I think these skirts are great for everyday, out-and-about looks because they pair so well with basic tops. Cher’s top was super casual, but it still made for a cute and cohesive outfit.

Look #3: Plaid and collars

OUTFIT DETAILS:

BLOUSE* (similar): Forever 21

SKIRT* (similar): Ben Sherman

SOCKS* (similar): ASOS

SHOES* (similar): J. Renee

For the final outfit, I took inspiration from a couple different looks that had the same kind of vibe to them. Looking at the fashion in Clueless, it isn’t hard to tell that a typical Cher outfit consisted of knee-high socks, a collared shirt, and plaid. That’s what I decided to go with here. This dark plaid skirt has been in my closet for ages, as well as the cream blouse I paired with it. And these gray knee-high socks were just too perfect not to wear.

Since my blouse has a somewhat sheer quality, I decided to wear it two different ways: tucked in and not tucked in. I preferred the look of the tucked in version, but one of Cher’s most well-known outfits featured a long, sheer blouse, so I couldn’t resist giving it a try myself. If you’re planning to replicate this look and not tuck it in, I would suggest going with a bit of a larger blouse. This way, it will be sure to hit the length you want.

All in all, I had a blast coming up with these outfits and piecing this whole thing together. Cher’s preppy style was fun to imitate, and I can definitely see myself taking inspiration from her outfits in the future. I don’t know where plaid has been all my life, but suddenly I can’t get enough of it.

Thank you so much for reading!

MORE POSTS LIKE THIS:

Friends Inspired Lookbook

Blog Outtakes

Polka Dots & Collars

When you think about iconic fashion moments in film, what are some movies that come to mind? 

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