The First Cool Item of Clothing I Bought Was _____ - Topic of the day 7/19/25
I mean...fill in the blank (no I am not defining "cool"). When/where/why did you buy it, and do you still wear it today?
This topic will run for 2 days.
24 Replies
Depends on how deep we dig:
- The first cool item of clothing I bought myself is probably a ~50s French chore coat that I got in 2014 and sold in 2025.
- The first cool item of clothing I picked for myself was possibly a Barbour Beaufort that I got for my 16th birthday in 2013. I don’t fit in this specific Barbour anymore.
- The first cool item of clothes I owned was probably the Barbour + Timberland 3 eye lugs combo I got from an aunt when I was 18 months old. I do not wear these specific pieces anymore.
The two purchases that have stuck with me from the early days post covid are the orslow fatigues (lmao) and the 4S Jacket which is the real cool one
Definitely my N(N) Converses I got in ~2016 or so and have used them as concert beaters as god intended. I don't wear them nearly as much anymore
BAPE Tshirt that my mate brought me back from Harajuku in liiiike 2005? Still wear it, it's kinda cooked in a great way, but the print is still perfect.
Homme Plisse pants
really went 0-100 there
First "cool" (questionable) clothing I bought with my own money were these sort of outrageous looking light-up basketball shoes I wore to my rural conservative catholic school that had strict dress code enforcement
I was maybe 13 and had just started working. I mostly bought them because they were technically not breaking any rules explicitly and I knew it would upset the school staff, and wore them for the first time when the local bishop came to visit. The lights on these were way bigger than the ones that people give to little kids
Sort of kickstarted a wild / antagonistic era of dressing for me that cooled down as soon as I moved out of the house
First pair of raw denim started it all :xd:
I don’t wear them because they are super slim but I want to do something with the fabric
first cool purchase was black gats
weirdly enough got them with money i made by flipping splatter gats i found in a charity shop that were a few sizes too small
I’ve got two! I bought these within like two weeks of each other when I was…based on hair probably my sophomore year of highschool. Snagged at goodwill. Vintage leather bomber and a milsurp jacket someone had sewn a Tibetan flag on. They both slapped. Miss em to this day
I think for me it was probably a pair of Surface 2 Air (anyone remember that lol) jeans I got in 2010 or so in Paris. Not sure if I have any pictures of them
This blue linen Haider suit from SS16. It was 2018, fashion had my attention in a way that it didn't before, and I was really looking at it with an eye toward trying new stuff and finding what i liked. This suit was the first Haider I ever bought, and I think the second thing I got off grailed.
This one I didn't really buy myself, but I thought was so cool at the time. It was 1992, my parents went on a trip to the Barcelona Olympics and I was staying at my cousin's for the summer. We went to the mall and I bought this all-red Cross Colours fit with like 2/3 of the spending money they left me.
I bought an apolis chore coat with the college graduation money that my grandparents gifted me because MFA said it was cool
This is super hard to answer bc it‘s so hard to just pick one so here‘s 2:
the jeans I bought at H&M in 2015 from my babysitting money and they were the first thing that allowed me to dress 70s adjacent like I wanted to, I wore these until the fabric wore through
I bought the blazer on the right at Kevin&Howlin in Dublin in 2016, it was my very first big-girl-purchase
It‘s Donegal tweed, I remember being super proud of owning such a high quality item, I really should wear it more
I’m not 13 and 14 in these pictures btw, in case that wasn’t clear:xd:
For me, Momotaro straight fit denim in like 2010. The painted back pocket stripes and pink inseam threads were 🤯
Ysl celtic belt in like early 2023. Was very fond of this (still am) and got really good at doing french tucks so that I could show my cool belt buckle
Turns out I do. I'm on the left. This was the day after buying them I think. My brother's fit on the right aged a lot better in hindsight lol
I have 3 firsts over the course of my fashion journey
1. Is a pair of Dr. Marten 1460 in Crazy Horse in 2018. This was the first piece of clothing I thought was genuinely cool and my first go at dipping my toes into “normal” fashion.
2. This brown tapered pair of Homme Plisse in 2019. I was very curious about contemporary fashion and fell into the Homme Plisse trend of that time (still a super relevant choice today obviously)
3. Around early 2021 I was very into the idea of Avantgarde clothing and all black fits from Yohji. I couldn’t justify the used prices at the time, but I found this great pair of Kansai Yamamoto SuperLADY culottes for like $50 online.
Some cowboy-boot styled side-zips from sendra I bought from my first wages as a student assistant post covid.
i didn’t buy it, but in senior year of highschool my dad gave me this USC trojans golden bear roughout suede chore/sport coat thing he was gifted when he was a professor.
if we count things i actually bought then it would be this misprinted band tee i bought from the artist at a show i drove 7 hours to get to for my 16th bday.
i don’t wear either of them anymore, because the suede jacket is like xl, maybe a double xl, and the shirt is so beat up that the print us peeling off, plus i got it autographed so i don’t want to wear it anymore, and also it’s a size too big
i don’t wear either of them anymore, because the suede jacket is like xl, maybe a double xl, and the shirt is so beat up that the print us peeling off, plus i got it autographed so i don’t want to wear it anymore, and also it’s a size too big
When I was 20, I bought ten blazers for a buck each from a thrift store.
They were old and worn out and none of them fit me, but it was the first time I really bought clothes for myself. Before then, I just wore whatever hand me down sweats my dad gave me To this day, those ten blazers remain the coolest thing I’ve ever bought, cause I bought them for me, because I wanted them.
They were old and worn out and none of them fit me, but it was the first time I really bought clothes for myself. Before then, I just wore whatever hand me down sweats my dad gave me To this day, those ten blazers remain the coolest thing I’ve ever bought, cause I bought them for me, because I wanted them.
Swimming-pool-tile scarf i got 3/4?? years ago. I remember agonizing over which colorway to get, and now 2 friends have said the teal version was better and that something being "tide pod-colored" is not a pro in its favour :hell:
i dont buy brand new all that often, let alone in person, so its special to me even if my friends are haters
