Introducing the Ultimate Anti-Trend NYC Wardrobe, Thought I'd Share

Watching Pretend It’s a City is like taking a trip to NYC without leaving your couch, which is probably why I flew through the entire series from start to finish in the span of two days. The show dives into conversations between New Yorkers Fran Lebowitz and Martin Scorcese, and it’s like being within earshot of a candid, captivating dinner party convo that you can't help but tune into. Needless to say, I’m a big fan and I’m telling everyone I know to watch it right away.

What was as good as the witticisms Fran Lebowitz sprinkled in throughout the show were her amazing outfits. Her style is just so good in a really classic New York way and it hasn’t changed much throughout the past 50 years. Decidedly anti-trend, she has a strong personal sense of style and has stuck to staples like straight-leg jeans, cowboy boots, and slightly upsized coats and blazers for as long as she's lived in NYC. Her wardrobe is living proof that a timeless capsule wardrobe can actually work for the span of many decades. Ahead, I'm taking a look at the key pieces Fran Lebowitz wears again and again that define her epic NYC wardrobe.


(Image credit: Getty Images/Time Life Pictures)

Up until last year, I never owned an oversize blazer and now I'll never go without one. Clearly, Fran Lebowitz was keyed into just how essential this piece is and has been wearing one for decades. Truth be told, it's one of the most-worn pieces in my closet that I pair with everything from mini dresses to sweatsuits.

Shop oversize blazers:


(Image credit: Getty Images/Larry Busacca)

Who knew cowboy boots were such a versatile shoe? While they were certainly a trend a few years back, this outfit is proof that they have a much longer shelf-life than just one season.

Shop cowboy boots:


(Image credit: Getty Images/Ray Tamarra)

If you haven't already heard, oversize button-down shirts are set to be one of the biggest trends this spring. They were all over the S/S 21 runways at brands including Valentino and The Row. This outfit is just another reason to add one to your arsenal.

Shop button-down shirts:


(Image credit: Getty Images/Ron Galella)

Knit polos are one of the biggest trends to emerge in the last year and Lebowitz was clearly an early adopter. If you've been on the fence, here's even further proof that this is a timeless staple.

Shop knit polos:


(Image credit: Getty Images/Charles Eshelman)

Jean trends—like the current uptick in baggy denim—come and go, but you can always rely on a straight-leg silhouette. They read as sophisticated and polished because they take on the shape of classic pants. Look for a medium-to-dark wash without any rips or holes, which is easiest to dress up or down.

Shop straight-leg jeans:


(Image credit: Getty Images/Ron Galella)

Whether you opt for a sweater or a sweatshirt, look for a crewneck shape with a slightly relaxed fit. An endlessly versatile layering piece, you can wear one layered over a button-down, tied around your shoulders, or on its own with jeans.

Shop crew-neck sweaters:


(Image credit: Getty Images/Astrid Stawiarz/Stringer)

A trench coat is something you can add to your closet that is as practical as it is stylish. You can't go wrong with a shade of tan or beige. Take a styling note from Lebowitz and try a long, slouchy version or buy it in one size up for a relaxed fit.

Shop trench coats:


(Image credit: Getty Images/Ron Galella, Ltd.)

Suiting is the trend that gets reinvented each season—and for good reason. There are so many cool takes on pantsuits that you're bound to find a cool, tailored one that will fit seamlessly into your wardrobe.

Shop pantsuits:


(Image credit: Getty Images/Jeffrey UfbergR)

Round sunglasses are a classic silhouette that become even more timeless when they're finished in tortoiseshell. You can throw these on with just about anything.

Shop round sunglasses:


(Image credit: Getty Images/Taylor HillTr)

A must-buy piece for any New Yorker? A great tailored coat. It's the winter wardrobe essential that you'll continue to get mileage out of year after year.

Shop tailored coats:

Next, shop 25 cool fashion finds I’m obsessing over right now.

Associate Director, Special Projects

Kristen Nichols is the Associate Director, Special Projects at Who What Wear with over a decade of experience in fashion, editorial, and publishing. She oversees luxury content and wedding features, and covers fashion within the luxury market, runway reporting, shopping features, trends, and interviews with leading industry experts. She also contributes to podcast recordings, social media, and branded content initiatives. Kristen has worked with brands including Prada, Chanel, MyTheresa, and Luisa Via Roma, and rising designers such as Refine and Tove, and her style has been featured in publications including, Vogue France, WWD, and the CFDA. Before Who What Wear, Kristen began her career at Rodarte, where she worked on assistant styling, photo shoots, and runway shows, and at Allure, where she moved into print and digital editorial. She graduated from the University of Southern California, where she studied art history and business, and currently lives in New York.