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.
1. Neutral Animal Prints
"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."
Shop the look:
2. Patriotic Look
"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."
Shop the look:
3. Sweet Country Girl
"This is every girl's dress. Your grandma, your mom, your daughter, and your granddaughter will all wear this dress."
Shop the look:
4. Big Pink 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."
Shop the look:
5. Crazy-Colorful Look
"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."
Shop the look:
6. Clear Boots
"These boots are fascinating. The possibilities of looks (good and bad) are endless."
Shop the look:
7. Checkered Leather Jacket
"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."
Shop the look:
8. Furry Quilted Coat
"Overdone and overwhelming. Nothing more to say. If you can't say anything nice, be quiet."
Shop the look:
9. Feather Dress
"The body of the dress has possibilities, but not a fan of the feathers. And those shoes—why?"
Shop the look:
10. Rainbow Shirt With a "Pink Beard Thing"
Shakes head. "No words."
Shop the look:
Next up, find out which fall trends celebrities wore 25 years ago.

Lauren Eggertsen is currently the editorial director ofBest Knockoff Luxury Clothing and has worked at the company for over nine years, where she started as an associate editor and has since worked her way up. Lauren has worked in the Los Angeles and New YorkBest Knockoff Luxury Clothing offices but currently calls L.A. home. Here, she leads and managesBest Knockoff Luxury Clothing 's editorial team and oversees all editorial content. Lauren's role also includes helping to set the fashion direction for all original photo shoots and often styles many celebrity cover shoots, including big names like Kaia Gerber, Normani, and Sabrina Carpenter. She has also attended multiple fashion weeks, including New York, London, Milan, and Paris, where her style has been featured on sites such as Vogue, Harpers Bazaar, and Elle.
-
Kristen Bell Swears Her Nobody Wants This Character Is Cooler Than Her
But it’s safe to say she would have approved of the actress’s flawless Armani gown for last night’s Emmys.
-
I've Worked in Fashion for 15 Years—Here's What I Actually Wear Every Day
Trends come and go, but my everyday wardrobe is made of pieces that feel like me.
-
Veronica Leoni's Second Calvin Klein Collection Masters Sensual Minimalism
Read everything there is to know about it here.
-
EverythingBest Knockoff Luxury Clothing Editors Saw, Wore, Did, and Ate During NYFW
Let's dive in, shall we?
-
Paris Hilton's World: Her Pink Motorola Razr, Favorite Y2K Looks, and What 11:11 Media Means to Her
A glimpse into the life of this savvy entrepreneur.
-
Pendant Necklaces, Desert Hues, and Pajama Sets—Michael Kors Ushers In Earthy Elegance for Spring 2026
Fringe, suits, and wallet necklaces were all standouts.
-
According to Ralph Lauren, Coastal Glamour Will Set the Tone for Spring 2026 Style
Bold pendants, XL sun hats, and stripes galore.
-
This Simple Fashion Person Approved Layering Technique Changed the Way I Wear My Basics
Effortlessly cool.
-
Scandi Style, Unfiltered: An Editor's Dispatch From Copenhagen Fashion Week
The Danes do it better.
-
Copenhagen Street Style Is Elite RN—7 Trends I'm Unashamedly Adding to My Wardrobe
I'll be wearing them now and during the fall.