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What to wear in New York in the fall 
A photo of the St. Regis Hotel in NYC.  The American, NYC and St. Regis flags are all on display over the St. Regis gold awning.

In this post...

What to wear in New York in the Fall

In this post, I will show you what to wear in New York in the fall. Our recent trip was for five days that included site-seeing, high tea, delicious breakfasts, as well as a very special dinner. I will show you what I wore and explain some packing tips.

This past week, Mr. G.Q. and I headed over to New York City for a fall experience. The main purpose of this New York City adventure was to meet (for the first time!) the parents of my youngest son’s girlfriend. The trip was a smashing success! Everyone got along swimmingly, as many stories were shared and much laughter was heard. We can’t wait to see Rachel’s parents again soon!

the gorgeous gold registration desk at the St. Regis hotel.

During our stay, we stayed at the St. Regis hotel at 55th and 5th. Above you can see the beautiful registration desk.

Beautiful flowers and a handsome clock in the lobby of the hotel.

And then the gorgeous flowers that adorned the lobby…

Outfit #1: (for a 5 day trip to New York in the fall)

My first outfit with a black blazer, a grey hoodie insert, white henley tee, white sneakers, black joggers, and a maple leaf pin on the jacket's lapel.

This fun outfit was very versatile in that it included a darling black Evereve blazer with a button-in hoodie attachment. This allowed the jacket to project a casual vibe when the hoodie was in place, and a more dressy, sophisticated one when it was removed.

Below, you see me in the middle of the Brooklyn Bridge (Check out this previous post-Brooklyn Bridge). I’m wearing a white Evereve henley tee shirt under the jacket, with black Loft Lou and Grey knit joggers. Because we walked 18,000 steps many days (!), I wore Asics gray sneakers along with a black Coach crossbody bag. I also paired it with white leather Cole Hahn sneakers for a different look.

Me on the Brokklyn bridge wearing the outfit described above.
a close-up of me with the black blazer, white tee and black joggers.

A neat detail to the jacket is that the cuffs have a contrasting striped lining. Style tips: Rolling the sleeves a bit to a blazer is a sure-fire way to elevate the look of that outfit. Also, adding a leather maple leaf pin is a neat seasonal detail that adds a pop of color to the ensemble. (More blazer posts: Early Fall Looks: Blazer, Cute Tops and Olive Pants, How to Wear a White Blazer Six Ways).

Outfit #2 (for a five day trip to New York in the fall)

second outfit with an olive green utility jacket, leopard slip-ons, dark wash skinny jeans, a dark floral tank and gold watch, earrings, and bracelet.  Lastly, an amber statement necklace.

This look pairs another pair of comfy shoes (CRITICAL in NYC!) in the form of leopard slip-ons with a dark floral Loft tank, and Wit and Wisdom Ab Solution skinny jeans in a dark wash. I added a light-weight olive green utility jacket, with a cowhide crossbody bag. My jewelry was all gold metal: an amber statement necklace, a watch, bangle, and gold hoop earrings. Style tip: By pairing the sleeveless tank with the utility jacket, I was comfortable in the early part of the day with the jacket in place, and still looked put together once I removed the jacket as the afternoon warmed up. Plan to wear layers that can be removed as needed.

This day we went to Brooklyn to see the sites. I’m standing in front of one of many colorful street murals.

Here is a photo of the lobby of the Wythe Hotel in Brooklyn. It’s a quaint spot with 70 rooms.

This is a shot of the bar and restaurant in the Wythe Hotel.

One of many flower stores we saw on the street of Brooklyn.

Fresh flowers with loads of colors! So seasonal and cheerful!!

This is a snapshot of a neat brown brick building with pretty ornate limestone trim.

Outfit #3 (for a five day trip to New York in the fall)

I have had High Tea at The Plaza on my bucket list for a long time. How lucky was I to be treated to this very meal by my son Jake’s sweet girlfriend, Rachel? It was a magical afternoon. We truly enjoyed ourselves. The service was terrific, the food was artistically prepared and delicious. The company was perfect.

Here’s a portrait of Eloise, from the whimsical story of the little girl who lived at The Plaza Hotel!

Of course, we toasted and drank champagne.

Here is the gorgeous caddy of amazing treats from the tea!

Here we were at the entrance to the lobby of the Plaza. I wore the same black jacket as in outfit #1, but I removed the hoodie. I added a leopard blouse and tobacco brown slim pants (called The Portland style from Talbots). My booties were black suede. I accessorized with a skinny leopard belt and a delicate amber beaded necklace. Rachel wore a darling pink boucle jacket over a black tank and slacks. Her pumps were pink suede. Two very lady-like looks for High Tea don’t you agree?

Outfit #4 (for a five day trip to New York in the fall)

This is what I wore to dinner to meet Rachel’s parents!! We had dinner at a very cool Italian restaurant called, Carbone. Everything was DELICIOUS!!! We were seated at the Captain’s table, where we received spectacular service!

My outfit was a colorful knit dress (last season) from J. McLaughlin. I love their dresses because they are comfortable and quite consistent in their fit. They frequently make their dresses in this style with a round neck, keyhole back button, and subtle pockets in the front. I will link below several current dresses from them.

I paired the dress with nude Stuart Weitzman D’orsay pumps, a medium wash denim jacket, and a fun Patricia Nash brown crossbody bag. I added a pearl bracelet and diamond stud earrings.

Outfit #5 (for a five day trip to New York in the fall)

This was a cute look for site seeing in Soho. I again wore the leopard slip-ons and Wit and Wisdom skinny jeans from outfit #2, but then paired them with a white long-sleeved tee from Lands End, a pink crystal necklace, and a very playful kimono. If I were wearing this to dinner, I would add nude pumps for a dressier look.

Do you know about this terrific book, Pretty City New York, by Siobhan Ferguson? It’s a wonderful, beautiful book about the many pretty places in New York. It would make a terrific Christmas gift for any New York lovers or those considering a future trip to the Big Apple.

Here’s a playful donut mural in Georgetown Cupcake Bakery in Soho.

Below are two photos of the gorgeous Ralph Lauren store in Soho.

Outfit #6 (for a five day trip to New York in the fall)

In this look, I paired the previous ( from outfit #2) green utility jacket with the skinny jeans and added a Banana Republic gray and white striped long-sleeved tee. This time, I wore white Cole Hahn sneakers, the cowhide crossbody purse, and a green beaded statement necklace. My necklace is from Francesca’s (old), so I have linked several cute new options. Style Tip: Wearing a statement necklace or earrings can really elevate an outfit, by combining all the pieces in a cohesive, elegant way.

Below, you’ll see the menu from Astor Court, which is the wonderful dining room at the St. Regis Hotel in New York. We enjoyed breakfast here most mornings, and each day had delicious fare.

Check out the gorgeous painted ceilings, chandeliers and murals!

a mural of blue sky with clouds and a crystal chandelier at Astor Court in the St. Regis hotel.

Outfit #7 (for a five day trip to New York in the fall)

pink/violet coat with tobacco brown slim pants, a brown crossbody bag, a denim shirt, and a vibrant pink, paisley scarf.

Don’t you just LOVE the colors in this outfit? This was by far, our coolest day for site seeing. It rained a bit, so a trench coat came in handy. I even wore black kid leather gloves. I wore my newest Rag and Bones suede booties for breakfast, but switched to gray Asics sneakers when we headed out to Chelsea for another VERY LONG WALK!

Don’t you love the pairing of the lilac/pink rain jacket with the medium brown crossbody and brown slim cut Talbots slacks? The bright Talbots scarf ties the denim shirt together with the rest of the outfit.

Rachel works at Madison Square Garden, so we had to snap a photo here. I also wore a black backpack for some of our walks, as it gave me a place to store my phone, my water bottle, and any extra clothing that I might need to add or discard in the course of our travels.

Both Rachel and Jake live in Chelsea, and here are a few of the beautiful flowers that we saw on our walks through their neighborhood.

Yup, thankfully, we will return to sweater weather in Chicago, so I can begin showing you the really fun fall clothes that involve lots of layers…

It’s so fun that all these flowers are just displayed right on the sidewalk. Where I live in the suburbs of Chicago, one goes to the flower center. But, here in NYC, it’s all available right in the middle of town! Amazing!

So, yes I definitely LOVE New York! If you haven’t been to the newly remodeled (totally overhauled!!!) La Guardia Air Port, you’re in for a treat! The place is spectacular. SOOOO clean, bright, and airy. The gates are comfy, with MANY recharging stations. The retail space is beautiful and accessible. Apparently, the remodel is ahead of schedule due to the low air traffic of the pandemic (a silver lining?!).

I hope this post has encouraged you to plan a fall trip to New York. I also hope you now feel comfortable that you know what to wear to New York in the fall. Happy travels!


Dr. Julie

PS Here are a few other posts on travel you might enjoy. Road Trip to Magnolia Farms…, What to Wear on a Fall Road Trip, My Packing List for Hawaii (for Ten Days), My Fun Fall Foliage Trip Around Lake Michigan!

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