Fashion Week Outfits That Should Never Be Forgotten Part 1
A mini-series as a reminder of the good days of celebrity style at fashion week.


This week will be the most back-to-normal-ish fashion week that we’ve seen since February 2020. Whether that’s warranted or not in terms of the pandemic, there will be dozens of in-person shows and parties without limits. Also returning are the fashion week outfits worn by hundreds of attendees off the runway.
This season, I can confidently assume that most outfits will fall into one of three categories. For the big shows, celebrities and influencers will wear head-to-toe outfits by the brand of the show they are attending. Others will wear something that stands out as they slowly walk by the group of street-style photographers clamoring to take the best photo. And the rest will be normal outfits, maybe punched up a bit for the occasion.
People look great. But it’s all just so put together. It makes me miss the less strategic outfits of the 90s and early 2000. So, throughout fashion month, I’m going to rehash some of these looks in the newsletter, starting with one of my favorites worn by a then 19-year-old Mary Kate Olsen to the Imitation of Christ show in 2005.
Olsen is seated next to Chloe Sevigny, making this a crown jewel of 2000s Fashion It Girl moments. She has a giant coffee thrown on the floor along with her jacket that she eventually removed for photos. The reason I always loved this outfit is that it is so clearly self-styled and a perfect example of the bobo (meaning bourgeois and bohemian) look she helped propel into a big trend.
She’s wearing an Imitation of Christ white silk dress which features a sequin neck and hemline. On her feet are a pair of black Roy Rogers cowboy boots that don’t exactly match. Over the dress, she’s wearing a green hoodie underneath a cherry leather biker, a signature of hers at the time that she clearly just threw on. Her accessories are completely bonkers, with nearly a dozen bracelets and several layered necklaces. Together though? It’s perfect. I love the idea of wearing a brand but actually showing your style, instead of just seeing a complete look that came off the runway on the street.
So, feast your eyes on this perfect look and come back for more throughout the week.

Courtesy of Getty Images

Courtesy of Getty Images