This fall, New York City feels like a sea of slouchy sweaters, baggy jeans, funky colors and big sneakers. It’s invigorating! So, last week, the Cup of Jo team and I hit the streets to ask people what they were up to and what inspired their outfits. Here’s what they said…

Naledi and Octavia
Occupation: Marketing manager (Naledi) and writer (Octavia)
Live in: Berlin

The highlight of our week: Naledi: “Coming to New York. We’re both half American and half German and are currently living in Berlin. We met there because we’re so fab! And our friend is getting married in Manhattan tomorrow, so today we’re getting manicures and preparing for the big day.”

The story behind my look: Naledi: “I don’t usually shop fast fashion, but I’d looked in every vintage shop for baggy pants and casual tops. When I couldn’t find anything good, I thought ‘f*ck it.’ I went to H&M for this shirt and these bottoms — I love the length. Then I have Martine Rose x Nike Shox and a Pink Siifu tote; and my glasses are from a Publix supermarket.”

My thought process while getting dressed: Octavia: “Since I was meeting up with my bestie, I wanted to be comfortable. But the sun came out, and now I’m burning up. My sweater is by Maska, my pants are from Sefr, and my shoes are Adidas Superstar.”

Mary Margaret (“How Irish can you get?”)
Occupation: Homemaker
Lives in: Berkeley, California

What I’m doing today: “My son and his wife live in Bed-Stuy, and I’m visiting them. He just turned 40. I can’t believe it. You can’t say, ‘I have a kid that is 40!’ This afternoon, I’m just bopping around. I just got a cone with cereal milk ice cream — it was delicious.”

My approach to style: “High and low is the thing for me. Here, my Vermont Country Store shirt is low, and my Anne et Valentin glasses are high. My pants — by Jag — are in the middle.”

Mayu
Occupation: Mother of four
Lives in: Soho, Manhattan

What it’s like parenting dogs and humans: “My three dogs take more energy than my four kids! I need clothes that are easy for walking quickly but still look cool.”

The story behind this look: “My hat and jacket are from the Hard Rock Hotel. We took a family trip to Atlantic City and went to the pool and amusement park. Everyone, including the dogs, ran around on the sand. The skirt is from Japan, and my shoes are New Balance.”

Faten Gaddess
Occupation: Photographer
Lives in: Nolita, Manhattan

How my day is going: “We had a rainy week, so I’m out enjoying the weather. Someone else just came up to take a picture of me, too. He usually sells his work, but he said ‘No, it’s for you.’ I guess this is my day!”

What I’m wearing: “My cardigan is from Uniqlo, many years ago. The pants were a birthday gift from a friend, and this is a vintage purse. Plus, a J.Crew shirt and Doc Martens.”

How I’d describe my style: “Right now I’m wearing neutrals, but I love colors. I’m like — I know the word in French but how do you say it in English — a rainbow.”

Megan and Kirisu
Occupation: Designer (Megan) and actress (Kirisu)
Lives in: Upper West Side (Megan) and Tokyo (Kirisu)

What we’re up to: Megan: “I work at a clothing store down the street called Les Miss. Kirisu is my cousin; she’s a musical-theater actress in Japan. She’s about to perform in a bunch of shows in Tokyo.”

What I’m wearing: Megan: “Today I’m going with earth tones. This shirt is by my tie-dye brand Plant Girl NYC. My pants are Le Gatte from Poshmark, purse is from Depop, and then I have my Uggs.

The story behind my look: Kirisu: “I like an elegant look, so I chose a vintage gold belt and gold jewelry. My dress is from Zara. The shoes are from a shop in Shimokitazawa, a neighborhood in Tokyo that is very popular with young people; there’s a ton of American vintage. And my clip is from the ‘$3 shop’ in Japan.”

Signe Pierce
Occupation: Artist. High-end dog walker. Energy guru. Renaissance woman.
Lives in: New York City and L.A.

What I’m up to: “Right before I walked the dog, I did an energy session with a girl, so the vibe is really pumped.”

How I’d describe my look: “I always dress bright. I’m a neon bitch, so this is a standard look for me. I got this jacket for $2 in Mexico City. These are workout shorts I’ve had forever. And the top is from Rainbow.

How the pandemic changed my style: “I’ve been going through a glow-up transition for the past two years, and my philosophy is you should be your higher self every day.”

Reggie
Occupation: Artist and designer
Lives in: NoHo, Manhattan

What I’m doing today: “Getting a smoothie from the Baya Bar and heading to the studio.” 

My life motto: “How you do anything is how you do everything.”

What I’m wearing: “I make clothes and sell online at @faithnsound. Right now, I’m wearing Faithnsound sweats, Faithnsound Pumas, Faithnsound hat.”

My top fashion tip: “Be yourself. Have a blessed day.”


For me, stopping strangers on the street to ask them questions was equally terrifying and exhilarating. Every time I pulled someone aside, I would think, “Are they down to chat? Will they reject me?!” In the beginning, we got a lot of ‘no’s because people were confused or in a hurry, but we persevered! And we also warmed up to it all. I’m thrilled that we did, because we got to peek into the lives and closets of so many kind and fascinating souls.

What styles are you wearing this fall? And which city would you like us to outfit scout next?!! Please share below…

P.S. Seven NYC City Hall weddings, and what Joanna learned after 20 years in NYC.

(Photos by Christine Han.)





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