I am going to NYC soon and I don't own any sensible shoes. I only wear heels to work or going out and the only flats I own are super cheap and have no support.
I'd like to purchase a pair of shoes for walking around, but I can't decide whether to go with a Sperry Topsider and try to dress super casual, or find a fun flat that I could dress up a little more.
I only have 1-2 pairs of jeans that are short enough to wear flats with, so I am thinking I should steer clear of the Sperrys just because of less outfit options.
My last resort would be get a pair of pumas or other stylish sneaker to wear with jeans and tees.
I'll wear my heels to dinner or when not walking too far. I just can't figure out to wear when sightseeing without loosing my sense of style.
I'd check out some of the comfort brands for flats - Me Too, Clarks, Born, Sofft, Cole Haan, Aerosoles, etc. There are some fugly options for sure, but I'm sure you'll be able to find something that's cute and simple enough to be versatile for you. Your best bet is to either go to somewhere like Nordstrom where you can try on a bunch of brands, and either buy there or do a huge order from somewhere with free shipping, like Endless or Zappos. Order as many as you can afford, try them all on and send back the losers.
Here are some possibilities from Nordstrom: $60$85$89 $100$110$120<these have a thicker heel, which helps alot $130$130$150
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I have a pair of Me Toos from a few seasons ago and they are extremely comfortable. Size-wise, I'm usually a 7 or 7 1/2 and I have wide feet. I took a 7 1/2 in the shoes I bought.
I like to bring my metallic flats with me when traveling because they can easily dress up a casual outfit and pretty much go with everything.
I second the Me Too rec. You can sometimes find them at places like Off-Broadway and DSW. I got my Nevada pair in black at Off-Broadway for I think $39. Larger size if you're between sizes is definitely recommended for Me Too.
I had a response typed and ready to go on my "smart" phone and it wouldn't let me post but I was also going to say try Me Too flats-they are soooo comfortable and cute. I also like Tory Burch Revas...