Style Advice Q & A

Comfy Fall Shoes and Booties to Wear in NYC

Hi Deborah,

I LOVE your website! I was wondering if you can give me some ideas for an upcoming trip to NYC. I am traveling with my husband, mother, and teenage daughters this fall, and we will be doing a LOT of walking around – visiting museums, going to the theater, and window shopping. Could you please advise me on what shoes (or short booties) to wear in New York? Thanks a lot!~Carol

Hi Carol,

I’m so glad you ask about shoes because they are the most important item you need to pack.  New York is a walking city, and you will be pounding the pavement for blocks on end. If your feet aren’t comfortable, you will be miserable!

I suggest you start by finding a great pair of walking shoes or booties and then work your outfits around them.  Brown, black, burgundy, dark green, or any other dark-colored shoes or boots are the best shoes to wear in New York since the streets are bustling and dirty. Black is also a favorite color of the locals, meaning you will fit right in.

Here are a couple of outfit ideas you can wear to walk around in, as well as some comfy booties and shoes to wear in NYC.

Red Sweater Slip On Comfy Walking Shoes



Slip-On Statement Sneakers

We all know that wearing clunky, lace-up white runners with jeans is not chic, so what kind of sneakers can you wear? New York is a sophisticated city, so why not go for sneakers with a touch of color and hardware? These burgundy suede slip-on sneakers fit the bill perfectly. Don’t they make a great site-seeing outfit with skinny jeans and a coordinating nubby oversized sweater? I have them in black – you might remember them from this post I did earlier this fall – and I LOVE them. They are feminine, comfortable, and go with so much.


Brown Wedge Cofy Shoes POncho



 Velcro Booties

If booties are more your thing, then take a look at these by Clarks. Clarks is well-known for its comfortable footwear. I particularly like this boot because it manages to pull off both chic design and comfort. The style is modern and the earthy brown and black look fantastic worn with black leggings. At the same time, it has a wedge heel and cushioned insole for walking comfort, as well as an elastic-gore panel that makes them easy to slip on. With a blanket poncho and stylish bag, there is nothing frumpy about this outfit!


Black sneaker COmfy Shoes White Sweater


Lace-up Sneakers

If you have a style personality that leans more towards the sporty side, then lace-up sneakers might be the way to go. Tread carefully here. (Get it? LOL) A battered old pair of sneakers will not look classy anywhere, New York City included. And heavy, white lace-up sneakers are dated. Instead, opt for a more modern, chic pair. Here I’ve chosen these suede and metallic lace-up sneakers by Rockport. These look great but equally important; they’re built for comfort with a grippy wedge sole and Rockport’s truTECH® technology designed for shock absorption.


Black Leather Walking Shoes


Chelsea Booties

This last look pairs a classic Chelsea boot with black jeans and a statement sleeve cardigan for a comfortable, on-trend look perfect for a weekend in New York. (With a long cardigan like this that covers your bottom, you can easily swap out the jeans for leggings, BTW.) Chelsea boots are a perennial favorite of stylish women of all ages, but it’s hard to find a comfortable pair for standing and walking in all day. These from Ecco are cushioned with an arch-supporting in-sole, so your feet stay happy.

Do you have suggestions for what to wear to New York City in October or November? What about ideas for shoes or booties you can wear walking around New York or any other big city? Let me know what has worked for you.


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9 thoughts on “Comfy Fall Shoes and Booties to Wear in NYC

  1. Hi, I am a Filipina who will be visiting NYC from November 3 to 12 and then going to LA on November 12 to 25. Can you give me some ideas on what to wear? Thanks

  2. I have a favorite pair of Teva booties that are also waterproof & they come in several colors. Great support & also stay dry in case of rain.

  3. Great article, thank you. Outfits for me are always best when put together around a nice looking comfortable shoe :-) And I live in flats at work on my feet all day.

  4. I purchased a faux suede skirt in saddle color. I need help with what top and shoes to wear with the dress. I am plus size at the top. Do you have any suggestions for me regarding the top and shoes to wear with the dress?
    Thank you,


  5. I cannot recommend riding boots for NYC. I wore my Frye boots (very similar to the Sam Edelman above) on a winter trip, and while seemingly comfortable wearing them, I wound up with a stress fracture. The doctor gave me a stern talk about flat-soled boots. I love my Merrell ankle boots – great support.

  6. It´s all about shoes! This is an excellent perspective because the most important thing is to be comfortable; build something around it! Thanks for the advice

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