One of my biggest fears (probably top five…) is that I’m going to turn into a straight up hoarder. I’m talking, need-to-call-TLC-asap kind of hoarder. I love to keep things, especially when there are lots of memories attached to them. Which is practically everything.
I’m not kidding, I have to force myself to throw away stuff. I recently got rid of ALL of my binders from middle school and high school. Just threw them all out without thinking twice. See ya.
Clothes are especially challenging. I love seeing a piece of clothing and remembering all the fun places I wore it! I went through my closet and pulled my TOP FIVE favorite pieces of clothing of all time. These are clothes that I not only love (let’s face it, I don’t have much in my closet that I’m not in love with), but that I also had a great memory attached to it!
ONE | Lilly Pulitzer dress
I love just about everything. The material, the length, the details. It’s definitely a different dress and I think that’s another reason why I like it!!! 

THE MEMORY | Senior Prom
TWO | Rowing Blazer

This is just so different and oh so special to me. I will likely never wear this again, but it’s pretty much amazing.

THE MEMORY | Henley Royal Regatta (2010)
(missing one of the guys!)
THREE | Lilly Pulitzer shift

I can’t get over this print. I wish I had bought more in the pattern. The giraffe print is fun without being overly giraffe-y! 

THE MEMORY | (post) High School Graduation
(My dad wore the matching tie!)
FOUR | J. Crew Shorts
These were the first pair of J. Crew bottoms that I could fit into! After years of Gap Kids and Abercrombie Kids (seriously not so much fun when you’re in high school), I was thrilled to wear a pair of shorts without them falling off!!! I used to try on clothes in J. Crew all the time just waiting for the moment when I could finally fit. It was a magical moment 🙂

They still fit, and I wear them frequently. While they are starting to look a little frayed… I just think they look loved.
THE MEMORY | First J. Crew shorts
(fun fact : this is the #1 google image for critter shorts!)
Last week on Instagram!

MEMORY | Lots of steps
I’ve worn these things for a LONG time. I love to think about all the different places they’ve been.
What are your top five pieces of clothing? What memories do you associate with them?

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Clothes with memories are the best kind of clothes to have! Thanks for sharing your stories. I love all of the pieces in this post!


Julia D.

I agree, clothing with memories are the hardest to part with. I don't know if I could pick five, but my grad (prom in the US) dress would definitely be up there. I think you could still wear that blazer if you wanted though, I can think of so many things it would look cute with.


I have the same problem! I've kept all of my notebooks and assignments from kindergarten on… I'm graduating college next spring and I don't have the heart to throw them away, but I also don't have the time to sort them 🙁

Katie's Bliss

I have a lot of trouble getting rid of clothes too. I have a few dresses that have sentimental value that I refuse to get rid of!


very old jcrew catalogs (back in 2000's when I started wearing their clothes), Lacoste polos, and retail shopping bags….keep things because I am eventually moving out of parents home so I can do what I want with them


I have the same sperries!! I would never let them go (even though I've only had them for about a year and a half). I also remember the first time I fit into something (namely shorts) from J Crew. I'm really small (4'11") to begin with, and I had to wait until freshman year in high school before I finally got my first pair (they're not as interesting as yours though, only khaki). But I still love them even though I STILL have to wear a belt with them.

Tyne Swedish

Perfect Perfect Perfect! Your clean and well put together looks are exactly how I would love to dress. I just always feel so…not me in them but your classy and well polished looks are to be applauded!