Style, What's In Your Closet?

What’s In Your Closet? with Kailyn Ailene

I’m so excited to share the second installment of “What’s in Your Closet?” with the lovely Kailyn Ailene! Kailyn popped up in my Instagram explore page shortly after I started my account and I love her take on preppy style. Kailyn’s posts always make me smile, as she truly seems to be sharing fun snapshots of her day. You can find Kailyn on Instagram @kailynailene–be sure to give her a follow! Thank you so much, Kailyn, for sharing your answers to these questions!


How would you describe your style, and what does your style mean to you?

Oh man, that is such a gigantic question! To me, my style is largely about comfort and assertion of self-worth. I like to feel as though I am choosing timeless brands that convey classiness over trendiness. I do tend to dress in a traditional, modest way, not because I’m stuffy, but because I’ve always just felt super comfortable that way! I have a lot of neutrals in my closet and some pink things here and there. Yes, my closet is mostly preppy brands but it’s a closet made of great finds from Poshmark, Plato’s Closet , and Mercari.


How has living in Maryland and Columbus, Ohio, influenced your style? Have you found your style shifted after leaving Maryland?

Another great question!! I was born in Annapolis but raised in Baltimore County. We left the city when I was in second or third grade. I didn’t really have a defined fashion at that age, I guess, but because I was surrounded by and was myself an inner city kid, that came with all the trendy inner city fashions, and also my hair was more accepted there. Moving to a rural small town in Ohio taught me to really dull down my fashion and to hide my hair. I felt that I went through periods of isolation that later led me into wearing exclusively all black, as the move from Maryland to Ohio was very depressing for me… eventually coming out of that phase, I began to see the way happy kids (and sometimes the snobbiest ones) dressed and I realized I wanted that, but that I wanted to create an inclusive preppy style instead of an exclusive one.


What part of your life has had the most impact on your personal style?

So I feel as though I segued into this without meaning to–there’s really no simple, pretty answer. Growing up was difficult for me, as I was often the target of racism from peers because I was “different,” which led to a lot of isolation. 

I think I really longed for something to make me feel included. So after being put off by all the happy preppy kids, I think I decided I wanted to be like them, and wish I was happy and “normal” . . . it kind of grew from there. Which is funny because now I love and embrace my everything. And there’s quite a large amount people of color on the prep scene! Ironically I do what I do now BECAUSE I want to show that we are here and we love preppy things just as much as the next person. 

On the other hand, my classic style of fashion came from watching my mother buy very expensive clothing that was always business casual. It wasn’t until I was an adult that I looked back and saw we went shopping for her much more frequently than we did myself . . . I’m not admitting to being a closet hoarder, but I would like to go on record and saying watching both my mother and younger sister have more clothing really created a drive for me to want security in my clothing. And every time I would buy a new item, my mother would make me “purge” as to not get a cluttered closet, while she and my sister had clothes that were barely fitting in their closets!! 🙂 I basically learned how to limit the amount of clothes that I had and to make them count. So each piece had to be functional as well as classic so it would stay in style throughout the years.


Who are your style icons?

@Belleoftheball45 really introduced me to the prep style, I used to love seeing her outfits as a tween on Pinterest!


Where are your top three places to shop?

J. Crew, Lauren James, and American Eagle (for jeans).


What are your five most special pieces in your closet?

Honestly, after the house fire my husband and I went through last year, I had to mostly start over! I did manage to save a favorite powder blue seersucker dress from Lauren James. I got it on Poshmark about five years ago. I am pretty sure it was my first shift dress. It’s memorable to me because its the first preppy staple I remember investing in. I also found the price to be perfect–I didn’t wanna drop all the money down on a Lilly Pulitzer, so this was the best thing. Now it’s my favorite dress. 

I wear it when I want to have a confident, easy go to look, often for a day out on the town where I want to look cute but feel great! I actually wore this dress my first time meeting my husband’s friends!


Kailyn, thank you so much for your thoughtful responses–I loved getting to know you better, and I can’t wait to keep following along on your style journey! 🙂

4 thoughts on “What’s In Your Closet? with Kailyn Ailene

  1. Loved this 2nd installment of “What’s in your closet?”

    I love how Kailyn expresses that preppy CAN be inclusive, something I’ve always maintained. Being classic is far more in-style than any trend!

    Great blog!

  2. I’m definitely a fan of prep and enjoy seeing other WOC embrace and sport their own style. I love Kaitlyn’s style! she’s young and vibrant and I love how she incorporate her equestrian love into her story. I’m glad I discovered her page as well. Such a pleasure to follow

    1. Hi Alghashiyah, thank you stopping by and for your comment! I love Kailyn’s style and I’m so glad I could feature her in this series 🙂 She is truly vibrant and I can’t wait to see what’s next for her. I hope you stay well and safe and have a wonderful Thanksgiving!

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