I Trend-Spot on the Upper East Side—5 Luxe Fall Pieces I'm Seeing on Repeat

If you're like me, you may have grown up with the glamorous 2000s TV series Gossip Girl. The show followed the lives of the overly dramatic, well-dressed Upper East Side teenagers and their intertwined stories of sex and scandal, but 12-year-old me brushed past all of that to instead watch the characters on the show I admired—the teens' fabulously opulent mothers. Lily van der Woodsen and Eleanor Waldorf aren't just impeccably stylish, over-the-top fictional characters, though. Their real-life counterparts are some of the best dressed fashion people you need to be paying attention to. Enter the viral Ladies of Madison Avenue Instagram and TikTok pages.

Created by trained womenswear designer turned documentarian Joshua Kamei, the man-on-the-street style account has risen in the ranks to become one of the best fashion follows of 2023. Sitting at just under 250,000 Instagram followers, Kamei takes his camera and travels to the hot spots frequented by the stylish, opulent residents of New York's fashion crowd. Think Lincoln Center performances, charity galas, and, yes, Madison Avenue. 

"If someone is fabulous, they are fabulous, so I ask them questions about style, not age. It seems to have appealed to people," Kamei tells Who What Wear, touching upon the fascination with the people he interviews and photographs. His subjects don't just include relatively unknown women walking down the street—they also include style icons like Carolina Herrera, Vera Wang, Diane von Furstenberg, Dominique Jackson, and his personal style icon, Aerin Lauder. 

While you can learn about your own personal style at any age, it's important to note the years and experience that come along with his older female subjects. "They are masters at accessorizing," Kamei gushes. It's not hard to understand why. A glimpse at the 600+ images Kamei has posted since starting the account shows that some of the city's longtime residents appear to be the most well-dressed. 

In the age of quiet-luxury and stealth-wealth aesthetics, it feels like Kamei's project is a firsthand account of the anti-trend movement that's slowly picking up steam. His thoughts on the matter, you ask? "I think it depends on the woman, but if you are wearing a Verdura necklace or Valentino or Christian Dior couture gown, I don't think it is really that quiet," he says. In the end, it doesn't matter if you're not wearing labels or wearing garments that cost as much as someone's rent. It's about truely personal style outside of what people expect you to wear.

"The women I tend to interview don't really focus on trends. They wear what works for them," Kamei explains, pointing to the colorful dresses, over-the-top accessories, and personal touches his subjects often wear on the street. "They are timeless but also appropriate to the occasion they are attending, whether it be a garden party or black-tie affair."

While every single subject has their own sense of style, it's safe to say it's all their own. There are a few key trends Kamei has noticed trickle down this fall and winter, though. From fabulous furs to sharp, immaculate tailoring, here are five must-know style tips from some of the most fashionable people in New York.

Faux-Fur Jackets and Vintage Boleros

There's nothing more opulent than a well-constructed, timeless fur or faux-fur cropped jacket, bolero, or coat. Opt for a neutral shade to keep your item looking extra luxe.

Shop faux fur outwear:

Over-the-Top Accessories

From "Holiday Golightly evening gloves" to opulent brooches, costume jewelry, and headbands, Kamei's number one style rule he's picked up over the years is to glamorously accessorize. 

Shop opulent accessories:

Little Black Dresses

Can you really go wrong with a little black dress? The timeless item has transcended years of style and trend to be the one item every stylish person always reaches for, no matter their age, fashion tastes, or personality. 

Shop little black dresses:

Sharp Tailoring

Just like the little black dress, Kamei has noticed his stylish interviewees opt for boxy, oversize jackets or men's Brooks Brothers tuxedo jackets draped over their shoulders. It doesn't get more timeless than this!

Shop blazers and other tailored essentials:

Understated Handbags

A quick scroll through @LadiesofMadisonAvenue proves that your outfit always needs a chic bag. Instead of unlivable, gaudy clutches, the fashionable Upper East Side crowd opts for big, functional, understated bags that look and feel luxe.

Shop understated bags:

Shop more quiet-luxury fall finds:

This post was published at an earlier date and has since been updated.