UPDATING MY MILLENNIAL PHOTO OUTFITS
Challenge
What if the ghosts of outfits past could come back—not to haunt us, but to help us? Hear me out—I’m just spitballing here—what if I take my most outdated, cringeworthy looks and transform them into something current, something chic, something... wearable?
While researching this year’s Halloween costume post, I stumbled upon a few photos showcasing fashion choices that haven’t exactly stood the test of time.
So, why am I sharing this with the world? Well, just like you don’t need to be a fashionista to look amazing in a photo, you don’t technically need a car to get around... but it helps. I hope this little project serves as some inspiration for anyone looking to refresh their photo-ready looks—and hey, the goal isn’t perfection; maybe we’ll have a few laughs along the way.
The first one’s on me, and the second one is behind the paywall. Enjoy!
P.S. Your likes have been working wonders for the algorithm, so if you enjoyed this issue and feel like tapping that little heart, it would mean the world to me!
Old photo #1
As I looked at the photo, I couldn’t help but reflect on how much my personal style has evolved over the years—and, even more, how my life has changed. I’m no longer in a warmer climate; now, I live in Chicago. I’m also no longer a student, and thanks to my career, I don’t have a specific dress code, which gives me extra freedom to prioritize comfort. Naturally, fashion has changed over the past decade as well. So, these are the updates I’ve made to keep pace with who I am today.
Changes:
I traded in my skinny gray jeans for something with a bit more structure—tailored trousers. Don’t worry, they’re still comfortable. I paired them with my favorite classic white tee, letting it peek out from under my sweater. It’s the simplest trick in the book to add a little bit of depth.
Cut-off boots haven’t made an appearance in years. I don’t need to wear boots as a necessary right now, so I’m choosing sneakers. If I had my way, I’d own them in every color. The toughest decision? Picking between my green or yellow pair. Honestly, either would’ve worked. As for the floppy hat—it had its moment, but it’s time to let it rest. It might make a comeback someday, but right now, it’s all about the cap.
I swapped the breathable shirt for a sweater because it’s getting chilly in Chicago. As you can see, I kept the original color palette, just making it more consistent with less contrast between the dark blue and light gray.
And this is how the new version looks.
The new look is a bit sharper but far from dull. The structured pants and cap add a modern edge, making it perfect for a cute photo but also practical—functional for my life now, which makes it feel authentic rather than disconnected.
Did you love this project? Want more?
Now, onto the second outfit...
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