Favorite Shoes to Wear in the City

Living in the city, there’s a balance of being practical and fashionable. People often ask if I wear heels on my commute to work. I do not. However, I do wear stilettos to go out in the city. That is me walking to hail a cab and walking into my destination. My feet, like most, can’t handle too much walking in stilettos. For all the other times, here are five of my favorite pairs of shoes to wear around the city!

1. flats

Flats are one of the easiest things to wear around the city. In NYC, rounded toe shoes do better because they don’t get scuffed up so quickly. I typically wear flats when heading to an event and then I’ll switch out of them for heels. I also tend to throw on my heels when I just need to grab a couple things from the bodega down the street.

2. boots

I love wearing 2-3 inch boots while running errands or heading to a meeting. The chunkier the heel, the easier it is to get around in the city!

3. sneakers

Of course I had to include sneakers. Thank goodness for the sneaker trend! Ride the wave, ladies. Ride the wave! I try not to wear the same sneakers I wear to the gym out in the city, but it sometimes happen.


4. chunky heels

Living in the city, I get lucky from time to time and have a meeting just a few blocks away so I just walk over in my heels. For these days, I wear my chunkier heels. They’re a little easier to get around in the city. Nothing worse than getting your stiletto stuck in a sidewalk crack! It hurts.

5. ankle strap heel

Here’s my secret. How do I always wear heels, well pain tolerance is #1 tip, but the second one is ankle straps. This ensures your shoes will not fall off or be too uncomfortable while walking around in the city. They give you a little extra support on your ankle and give you a few extra hours in heels than would be normally. Just make sure your shoes are broken in! Good luck:)

Did I miss any? What are some of your favorite shoes to wear in the city?

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xo, Olivia



  1. Jherell wrote:

    I agree – thanks goodness for the sneaker/athleisure trend! I’m taking a trip to Boston soon, so I think I might need a pair of those Nike Juvenate sneaks!

    Posted 2.15.17 · Reply
    • Right!? Yes! Thank you sneaker trend. Those Nike Juvenate have been all over! I think I’ll be joining you. I need a pair, as well!

      Posted 2.15.17 · Reply
  2. Liv wrote:

    Great picks! I agree with the booties, you need a chunkier heel for more comfort!



    Posted 2.15.17 · Reply
  3. I have a three inch rule. Anything under I can rock all day, anything over and I don’t even buy.

    Posted 2.15.17 · Reply
    • Hi Erin! That’s a good rule. A lot of my friends do the same!

      Posted 2.15.17 · Reply

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