The Craziest Street Style Moments, Ranked by My 93-Year-Old Grandma

Street style is known for being a bit, well, out there. To those of us who either work in the industry or are simply fashion-obsessed, the shock of these outside-the-box outfits kind of just wears off over time. But to someone like my 93-year-old grandmother, the street style looks we don’t bat an eye at have her feeling some type of way. In an effort to really get a rise out of her, I decided to pull 10 street style outfits we’ve seen over the course of fashion month that even I was shocked by. If these looks were causing me to do a double take, I could only imagine what my grandmother had to say about them.

To preface, my grandma is quite a stylish woman and always has been. For her most recent birthday (the one where she turned 93), we took her shopping because all she wanted was some new animal-print pieces to add to her fall wardrobe. In other words, she is pretty open when it comes to trends and variations of style. Ahead, I had her rank the 10 street style images I chose for her from her personal favorite to her least favorite. In addition to naming each of the looks, she provided a brief explanation for each. Her commentary is both extremely spot-on and extremely hilarious, so I highly encourage you to scroll all the way to the bottom to see which street style outfit resonated least with her personal taste.

“This one is my favorite because the prints look like natural surroundings. All the prints go together yet are different, and this look has so much style. I relate to this look because I like the cut of all the pieces, and I would definitely wear that jacket, even now.”
“This look represents things I believe in and respect—our country, the flag, and honor. I really like the medals and pins on the jeans. The flag is always fashionable, and there it is! I also love how everything matches head to toe.”
“This is every girl’s dress. Your grandma, your mom, your daughter, and your granddaughter will all wear this dress.”
“I like how this dress is feminine yet almost overpowering. I can really appreciate the detail work on it. Also, it is full enough to wear whatever shoes you want, including slippers. No will ever know.”
“This one has crazy matching going on. I love the colors repeated throughout, but the blouse print doesn’t belong, in my opinion. It is a distraction.”
“These boots are fascinating. The possibilities of looks (good and bad) are endless.”
“I like how this one is put together, but it is more of a look for a teenager. The shoes are not helping the look.”
“Overdone and overwhelming. Nothing more to say. If you can’t say anything nice, be quiet.”
“The body of the dress has possibilities, but not a fan of the feathers. And those shoes—why?”
Shakes head. “No words.”

Next up, find out which fall trends celebrities wore 25 years ago

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