The Best Shoes for NYC in Winter

most comfortable walking shoes for New York City — My go-to walking shoes for New York City

As a NYC local, I often get asked about the best shoes for walking around NYC. It’s a great question!

Whether the question is asked by my own family and friends, or a reader from this website, the answer is always the same. So, I thought it’d be helpful to roundup the best shoes to wear in New York City for anyone planning a trip. Longtime readers on this website know that I’m not one for small talk, so let’s get to it!

Best Shoes for Walking Around New York City — Shoes | Similar Wool Coat

Short on time? Here’s the shoes in my closet

Best Shoes to Wear in New York City (Fall & Winter)

Visiting New York City? If you haven’t decided where to stay (yet) check out our helpful guide on Where to Stay in New York City (The 10 Best Neighborhoods for First Timers & 3 to Avoid). Don’t have time? Here’s my favorite hotel in NYC, hands down.

Quality Winter Boots

In my opinion, these exact boots are (overall) the best shoes to wear while visiting NYC in winter. The reason? These boots are made for all weather conditions (rain, snow, etc). Making them the obvious choice if you’re looking to pack light (you won’t need any other shoes while visiting NYC, seriously).

I’ve owned my pair for 3 years and still wear them daily from November – March. There’s a short break-in period (maybe a week?) but the shoes mold perfectly to your foot so the short break-in period is worth it.

I recommend these boots to all my friends and family and am happy to report that everyone seems to love them too!

cute boots NYC — My favorite pair of stylish winter boots, they’re so comfortable I can easily walk miles in them. The only catch? They’re sold out everywhere, here’s the only place they’re still in stock.

Shopping on Madison Ave in the Upper East Side — As requested, here’s the coat I’m wearing (my go-to winter jacket) & checkered boots

Loafers

There’s two ways to go here, chunky or not. During the cold fall and winter months, most stylish New Yorkers transition to chunky loafers paired with socks. These seem to be the loafers of the hour in NYC.

But hard lol at the price (for me at least). My loafers are a souvenir from Lisbon but these popular loafers are very similar and equally comfortable. Quick Note. if you’re looking for comfortable shoes to wear while walking in NYC, loafers are not great for long days. So, save them for a nice brunch date or fun event.

Central Park · Central Park

Most Comfortable Shoes for Walking Around NYC (Spring & Summer)

Hoka Sneakers

When it comes to the most comfortable shoes for walking around NYC, Hoka’s are my go-to. They were recommended to me by my podiatrist when I started feeling a bit of ankle pain (here’s the exact pair he recommended).

Admittidely, Hoka’s aren’t even in the same timezone as stylish, but honestly, I couldn’t care less. After owning a few pairs over the past 6 years, I can confirm that these are the best shoes to wear in New York City.

Hokas work miracles on my tired feet and (easily) carry me for 10+ miles without issues. I’m on by 5th pair and plan to get another when these wear out.

Adidas Samba

If you’re keen to look fashionable while walking around New York City, you’ll be hard-pressed to find a more stylish and comfortable shoe than the original Adidas Samba.

I’ve recommended this shoe to so many friends over the years and hear nothing but rave reviews. One of my friends is actually visiting Rome right now and texted me a photo of these sneakers near the Pantheon with a cheeky caption reading “best purchase ever.”

Seems like she’d sleep in them if she could, can’t say I disagree. During the summer months you’ll notice a ton of folks wearing Sambas because they’re a great mix of fashion and comfort.

Easily the most comfortable shoes to wear while walking around New York City, if you want to look fashionable.

Onitsuka Tiger Mexico 66

Unlike the Adidas, Onitsuka Tiger isn’t as well known in the US (they’re very popular in Japan and Europe). But, you’ll still see this stylish pair of comfortable sneakers on the subway and streets of New York.

If you root for the underdog (or like being unique) opt for a pair of Onitsuka Tigers over the Adidas Samba. But honestly, you can’t go wrong with either pair, both are great for walking around New York City.

NYC Footwear (Helpful Tips)

Break in your shoes before visiting NYC

This sounds like a no-brainer, but it’s worth mention. During my first trip abroad, I wanted to look stylish and packed a new pair of sneakers. It was a disastrous mistake that resulted in nasty blisters and frequent breaks from walking.

I was so uncomfortable for the first few days and ultimately resorted to wearing my trusty sandals. It was an amateur mistake on my end, and one that is easy to avoid. My advice? Break in your shoes before visiting NYC, it’ll make your trip more enjoyable.

Closed-toed shoes are the best

For all the love I have for NYC, I’m not afraid to admit her faults, she’s a (very) dirty city. When I first moved to the Big Apple, I’d throw on a pair of sandals while walking around NYC and could not believe how DIRTY my feet were! Set yourself up for success and pack closed-toed shoes when visiting New York City.

Best Shoes to Wear in New York City (Post Summary)

Quality winter boots (Pair A | Pair B)
Ankle booties (Option A | Option B)
Loafers (Option A | Option B)
Adidas Samba
Onitsuka Tiger Mexico 66
Hoka Sneakers (Option A | Option B)

I hope you enjoyed this quick roundup of the best shoes for walking around NYC If you have questions, comments or suggestions, feel free to add your two cents below! I’m sure other readers would find it helpful, too.

Cheers!