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 Does this look too outdated?”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


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


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


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


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


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


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!






58 responses to “I Dressed Like Ashley Banks from The Fresh Prince for a Week”

  1. Lyka Avatar

    I love all these outfits! They definitely look great on you especially the one with the top and highwaisted skirt. Keep slaying! xx

    1. Cassandra Rose Avatar

      Thanks girl! That one was definitely my favorite look even though it caused me the most anxiety ha!

  2. Laura Dove Avatar

    Gorgeous !I think the last one is my favourite. It’s more casual than the others but you look really relaxed in it, I love a plain white vest!

    1. Cassandra Rose Avatar

      Thank you so much! It was so comfy that I ended up wearing it a second and third time 🙂

  3. missymjblog Avatar

    Love these outfits! Would love if you could check out and follow my blog https://missymjblog.wordpress.com/

    1. Cassandra Rose Avatar

      Thanks! I’ll definitely check it out 😀


    I love the clothing selection it looks super comfy. That black dress is my favourite – I am obsessed with dresses.

    1. Cassandra Rose Avatar

      Thank you! It was sooo comfy.

  5. A Busy Bees Life Avatar

    What a great and creative idea. You really pulled it off and look awesome. My favourite is day 3 xoxox

    1. Cassandra Rose Avatar

      Thanks so much! That overall dress was so cute and only 18 bucks :O

  6. Yukti Avatar

    Loved all the looks and specially that black floral dress on Day 3. Day 2 dress looks quite professional and can be worn in office too.

    1. Cassandra Rose Avatar

      I totally wore #2 to work!

  7. helerinablogs Avatar

    You look fab! What a brilliant idea this is. I really love day 6 outfit and you look so happy to be wearing that one.

    1. Cassandra Rose Avatar

      Thank you! I really loved that dress!

  8. Via Bella Avatar
    Via Bella

    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.

    1. Cassandra Rose Avatar

      YES, I practicially live in those jeans!

  9. Anastasia Golovko Avatar
    Anastasia Golovko

    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.

    1. Cassandra Rose Avatar

      That’s so sweet of you to say, thanks!

  10. Ana Ojha Avatar

    I loved all your outfits! You look absolutely gorgeous in each of your outfits and nailed it!

  11. Megan Okonsky Avatar

    This is amazing lol. You are such a ray of light! I want chokers to come back forever.

    1. Cassandra Rose Avatar

      Thank you! Now I’m trying to figure out how I can incorporate chokers into my everyday look haha.

  12. Miss Monèt Avatar

    The day 1 velvet dress just screams 90s!! I love it. And the day six look was spot on Ashley Banks. The 90s was a great era of fashion. Your style choices could also fit for Clueless inspiration, as well as, Sister, Sister.

    Miss Monèt

    1. Cassandra Rose Avatar

      I was *really* feeling that velvet dress! It’s definitely not something I would have picked up on my own if I wasn’t trying to channel Ashley, but I think it came out well!

  13. fellybee Avatar

    MOVE ON OVER ASHLEY! You just killed her look! Love it!

    1. Cassandra Rose Avatar

      You’re so sweet, thanks girl!

  14. Dreaming of Many Ventures Avatar

    You look so great in all of the outfits! I love the Fresh Prince of Bel-Air but I never would have thought about basing my outfits on theirs. Apparently, I should have been though!

    1. Cassandra Rose Avatar

      Half of my time is spent binge-watching the show and wondering who their costume designer was haha! Thank you 😀

  15. Adine @ Average To Awesome Avatar

    It’s so fun to see these looks, I remember them from ‘back when..’. However, they actually look great on you, while they ‘should’ be dated 😉

    1. Cassandra Rose Avatar

      Thanks for the compliment! Give me a pair of overalls any day ha!

  16. relmstyleco Avatar

    Love this post! You are so creative, love day 4!

  17. Jess Avatar

    Ashley was always my favorite. I adored her style and her personality. The looks we’re too cute!

    1. Cassandra Rose Avatar

      She was the BEST. I think she was one of (if not the) best dressed characters in 90s TV.

  18. Sosi's Mom Avatar

    I really like days 3 and 7!

  19. Charrise Avatar

    I love fresh prince of bel-air and everything about the 90’s. Great looks

    1. Cassandra Rose Avatar

      Same, I could watch that show forever!

  20. goingwithhappy Avatar

    Such cute outfits! I think the floral overall dress is my favorite.

    1. Cassandra Rose Avatar

      I love that look too! I tend to stay away from dresses that make me look younger than I already do but it’s definitely become a repeat outfit XD

  21. Star harford Avatar

    I love the Fresh Prince and you have managed to capture the style really well! You look absolutely amazing in all those outfits!

    1. Cassandra Rose Avatar

      Thank you! 90s fashion is the BEST.

  22. eliza casipagan Avatar

    Very nice combinations! you nailed it! I so like the 4th day outfit, look so comfy and basic yet you’re being stylish and creative shine.

    1. Cassandra Rose Avatar

      Thanks so much for the compliment! I can definitely see myself rocking her entire closet again.

  23. Kristine Nicole Alessandra Avatar
    Kristine Nicole Alessandra

    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!

    1. Cassandra Rose Avatar

      I totally wore that outfit to work (even though the sweater is actually cropped) and couldn’t agree more!

  24. Rose Sahetapy Avatar

    Thanks to bring us back to the 90s trend. You look lovely and the outfits are fabulous. I just love your creativity on creating these looks.

    1. Cassandra Rose Avatar

      Thank you so much! My style is pretty much living in the 90s these days 😀

  25. Christopher Mitchell Avatar

    With that title, you already won me over, and you pulled it off in spades! That skirt on day 5 is all kinds of vibrant! Love the post idea and the photos!

    1. Cassandra Rose Avatar

      Thank you! Day 5 was one of my favorites 🙂

  26. Aditi Avatar

    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!

    1. Cassandra Rose Avatar

      It’s such a great show! I love how nostalgic seeing everyone’s outfits makes me.

  27. beccajtalbot Avatar

    I love this post – I grew up in the 90s, so while these trends may seen a little odd now, they were all the rage back then. Skirts over trousers was a BIG thing, I can tell you! x

    1. Cassandra Rose Avatar

      OMG yes! I’ve totally been guilty of the skirt over trouser look in my past haha

  28. Elizabeth O Avatar
    Elizabeth O

    I really like your entire outfit. and what i really want the most is the black dress in day six. You rock your dress.

    1. Cassandra Rose Avatar

      Thank you so much! I was feeling a little self-conscious about the dress at first but now I love it!

  29. […] things: a brow pencil, nude gloss and eyeliner. Although the show ended over 20 years ago, her 90s style still inspires […]

  30. nicholasjlennox Avatar

    thank you ???? That overall dress was so cunning and only 18 bucks :O

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