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

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(Image credit: The Style Stalker)

"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

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(Image credit: The Style Stalker)

"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."

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3. Sweet Country Girl

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(Image credit: The Style Stalker)

"This is every girl's dress. Your grandma, your mom, your daughter, and your granddaughter will all wear this dress."

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4. Big Pink Dress

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(Image credit: The Style Stalker)

"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."

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5. Crazy-Colorful Look

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(Image credit: The Style Stalker)

"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."

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6. Clear Boots

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(Image credit: The Style Stalker)

"These boots are fascinating. The possibilities of looks (good and bad) are endless."

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7. Checkered Leather Jacket

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(Image credit: The Style Stalker)

"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."

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8. Furry Quilted Coat

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(Image credit: The Style Stalker)

"Overdone and overwhelming. Nothing more to say. If you can't say anything nice, be quiet."

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9. Feather Dress

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(Image credit: The Style Stalker)

"The body of the dress has possibilities, but not a fan of the feathers. And those shoes—why?"

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10. Rainbow Shirt With a "Pink Beard Thing"

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(Image credit: The Style Stalker)

Shakes head. "No words."

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

Lauren Eggertsen
Editorial Director

"Copy (200 words): Lauren Eggertsen is currently the editorial director of Who What Where and has worked at the company for nearly seven years, where she started as an associate editor and has since worked her way up. Lauren has over 10 years of experience in the fashion editorial space, starting her career with internships at Marc Jacobs, Marie Claire, and The Zoe Report, where she was later hired as their editorial assistant. Lauren has worked in the Los Angeles and New York Who What Wear offices but currently calls L.A. home. It is here where she leads and manages Who What Wear's fashion team and oversees all day-to-day editorial content and large tentpole moments. This includes all of the runway, trend, and shopping-driven content that ultimately helps to build a strong brand reputation within the industry. Lauren's role also includes helping to set the fashion direction for all original photo shoots and often styles many of the celebrity cover shoots, including big names like Sydney Sweeney, Lindsay Lohan, and Megan Fox. 


She has also attended multiple fashion weeks, including New York, London, and Milan, where her personal style has been featured on sites such as Elle.com, HarpersBazaar.com, and Vogue.co.uk. She prides herself on discovering and supporting small brands and on her knack for a good vintage shopping find. When she isn't working, she enjoys researching and dining at reputable restaurants around both her neighborhood and the globe.