I Dressed Like Ashley Banks from The Fresh Prince for a Week

One character who consistently slayed the 90s with her style is The Fresh Prince of Bel-Air‘s Ashley Banks. As a fan of the show and actress Tatyana Ali, I use any opportunity to copy her riskier style choices. Recently, I was in the middle of watching an episode when the idea to dress like the 90s style icon came to me.

Now I finally had an excuse to binge watch the show for the fourth time. Anyone who is a fan of The Fresh Prince knows that Ashley’s style stole the show every single time. It was fun watching her style evolve every season. She was the epitome of the 90s fashion “It girl”. From her casual overalls to her trendy thigh high socks, Ashley’s style was super accessible.

I put a lot of planning into the outfits I chose, and gave myself specific guidelines. I didn’t want to just recreate her most popular outfits; I wanted to add my own personal style to them as well. Another thing I was worried about is the fact that Ashley and I have very different styles. I’m obsessed with dresses and feminine pieces where Ashley was more of a tomboy on the show. Confidence also played a huge factor. Ashley is more known for her love of cropped shirts and mini skirts. Now don’t get me wrong. I love a good cropped top, and usually pair it with high waisted skirts and pants. As a twentysomething woman who ranges between a size 14 – 16, I wasn’t sure how I would pull off some of her more daring looks without it seeming too forced.

“Am I trying too hard? Does this look too outdated?” are a few of the questions that crossed my mind as I prepared for the following week. Keeping my original vision in mind, many of my final style choices seamlessly blended 90s fashion and modern trends.

Day One

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On the first day, I ended up hitting two 90s trends at once. Two popular looks from the 90s were pairing a long sleeve shirt with a dress, and wearing velvet everything. Ashley was very big on layers, which is what inspired this outfit. I dressed down this dress for girls night by pairing a plain white shirt with suede oxford shoes and tights.

Day Two

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On the second day, I channeled Ashley’s preppy vibes with a white sweater and flowy skirt. Full disclosure: This sweater is actually cropped! I loved this look so much that I ended up wearing it to work, and just tucked the shirt into my skirt.

Day Three

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By day three, I was really feeling myself. I could do this in my sleep. Red lipstick? Check. Printed overall dress? You bet. Here I am finding any excuse to walk around in my Ashley-wannabe outfit.

Day Four

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On day four, I wanted to go full out. You can’t pretend to be Ashley Banks and NOT wear a cropped-something or baggy jeans. You just can’t. I was feeling confident. I walked around the mall like I owned the place. I took myself out on a solo movie date. Boyfriend jeans have steadily become my happy place.

Day Five
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It’s day five and I’m in it to win it. My best friend was having a 90s birthday party so I knew I had to up the ante. This high waisted skirtall from Urban Outfitters was the best thing that ever happened to me. Although this look was out of my comfort zone at first, I knew I wanted to do it right. I picked up the shortest crop top I could find, pulled out my  twin chokers and werked it. For those of you who want to know, I did, in fact, party like it was 1999.

Day Six

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On day six, I transformed into Ashley completely. By now, rocking thigh high socks and red lipstick was second nature to me, so I needed to do more to distinguish my own style from Ashley.  That’s when I walked into H&M and fell in love with this sweater dress. Guys, I had plans for this dress. I took a day trip to Philly, and pretended that I wasn’t freezing my butt off as I strutted down the sidewalk and ignored the weird looks I got from strangers.

Day Seven

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Out of all the outfits I wore to channel Ashley, this one was the complete opposite from my personal style. I wear a dress everyday of the week, everywhere I go because it’s simple and quick. One of the reasons why I love Ashley’s style so much is that she doesn’t have to try hard to look fabulous. All she needs is a pair of baggy jeans, a flannel shirt and she’s good to go. No fuss, no problem!

Which look best represents your own style? Share or re-pin if you enjoyed it!

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Cassandra is a beauty and lifestyle writer. She spends most of her time treating herself to dinner and movie dates, pretending her life is a Marvel comic and figuring out how to keep her makeup on her face. Not necessarily in that order. Follow her on Instagram at @_cassandrarose.

58 thoughts on “I Dressed Like Ashley Banks from The Fresh Prince for a Week

  1. I could do the day 7 every day of the week. Lol it’s the most comfortable look of all. The other one I thought looks great on you is day 4.

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  2. I can see myself dressed my self all the time. Also, I’d like to compliment the photography. Every shot looks really good without context also.

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  3. I love the white sweater and flowy skirt ensemble. That would be a perfect fall outfit. Thanks for sharing your style inspirations. All of them are great!

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  4. I havent seen that show but I can guess Ashley’ style is to look out for, I’ll try to watch it, now that you have said so much about it. Loved all your outfit picks!

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