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I really like my Jessica Simpson Leve ballet flats. I get blisters from everything and these are so comfy for me! I throw a Dr Scholls insole in them just to give a bit more support and air circulation. I have three pairs of black ones (I bought some to keep in reserve, I'm terrified they're going to stop selling them!) and one pair of white.

@bakerella: Those are super cute. Do they stay on well? That's one issue that I've had with shoes for years... I think I finally figured out that it's because my arch is so high it's actually above the side of some shoes.
These are my go to shoes.
Winter:

Ugg BroomeII

Aquatalia
Summer/Warmer weather:

Sperry Top Siders
Steve Madden (although these don't have much support and can hurt my back after a while).
I love these too, I walked ALL over italy in them:

asics tiger (comes in TONS of colors)
@KatNYC2011: Ooo, the top siders are a good idea. They give me total flashbacks to childhood (those and similar beaded moccasins were all over the little mini preppy kids in my elementary school) but I bet they'd look really cute under jeans.
I'll check out the asics too - I ordered some basic black pumas a few days ago but need to at least exchange them because they're too big and now I'm having second thoughts on them.
I can't find the exact shoes I usually buy (softspots brand)... but I pretty much always have a pair or two of shoes that look like these as my "everyday" winter/fall shoes:

I like them because they look good with either jeans or work pants and they're super super comfy. When I'm going to be out in the snow I wear a pair of boots like this:

In the summer I generally stick to flip flops. My current pair I bought for the wedding and they look like this except they're sparkly... love them!

@Entangled: I haven't had any problems with them falling off. Maybe something like a kind of mary jane strap would work better for you then if you fall out of shoes easily?
@Entangled: I LOVE my topsiders. But, I tend to embrace my inner prep. They have some really cute ones now.
I love these gold ones:

Ooh ooh! Look at these ones! So cute! Okay there are about a million in the mary jane section on shoes.com that I think are adorable! Maybe look there. I won't want to bombard you with 8 million links ;)
They're not that cute, and they don't look like they offer much support, but I can walk for hours and hours when I wear my TOMS.

if you like the shoe look, I have never had more comfortable shoes than my sperrys! I'm a hardcore flipflop girl but I can't resist the boat shoes every now and then
I LOVE My Cole Haan Nike Flats. They are so comfy and I wear them to work almost every day. I like them because they look dressy but have the support of Nike sneakers.

@sloth: YES I second TOMS. Plus, for every pair you buy, they donate a pair to children who don't have shoes. http://www.toms.com/
I have the gold glitter ones, and seriously I get compliments on them all the time hah.

Thanks for all the suggestions!
@CorgiTales: I like the first one (and I think that brand comes in wide which is always a bonus). I'm still paranoid about the falling off issue, but may give them a shot.
@bakerella: I was looking at the mary jane section on Zappos though I'm pretty picky about how they look... there's a pair of Clarks that I may order though.
@sloth: I've seen Toms before on weddingbee... I'm not so big on the look but for 50 bucks may have to give them a try.
@etrebin85: Those are super cute, though I've found that the Cole Haan Nike Airs I've tried are just not built for my feet (sooo narrow on me). Which was a massive disappointment because I loved the amount of support.
One word : KEDS ! Check out keds.com. They are those sneakers that we wore as children! ( not sure if you did, but they were so big when we were kids). They are trendy, , yet original, super comfy, and great for spring ensembles! Check out keds.com. You can even deign your own for an extra 10 bucks! They are sneakerish though, yet summery, and remind me of an east coast beach vacay.
@NauticalBride2011: Those are so cute. I can't really see myself wearing them though. Probably because I am boring and afraid of things not matching.
@Cash000: Those were totally huge when I was a kid, too. I grew up on the east coast, near the shore so yeah they were all over. I will check out their website, thanks.
I've been loving some Aerosoles - I know they're known to be old lady shoes, but seriously they have some cute styles these days and they are SO comfortable.
I'm rarely in flats or sneakers but these heels I could walk around town all day/night in.
these ones are pretty cute:
SANUKs...hands down my favorite comfy shoe. Lots of colors to choose from and the yoga mat inside of them are so squishy 

@bakerella: Wow I can't believe you posted those! Those are my ALL TIME FAVORITE SHOES. Just to give you guys an idea of how comfy they are- I actually wore them hiking through Israel! 100% recommend!!!
@lilmiss26: oh wow I never thought to see if sanuk made real shoes! they are my favorite favorite flipflops! (yoga mats!)
I LOVE my Dansko clogs. Not the cutest, but I promise they look great with jeans! I am on my feet a lot at my Elementary school internship and at work (at a restaurant). They were recommended to me by a nurse and a teacher. Seriously the BEST. I just bought another pair today! http://www.zappos.com/dansko-professional-brown-leopard-patent
Despite their absurdness, I love my crocs. They are so comfy. Clunky, but comfy.


These are by Mudd, I love them, they will start smelling though so I wear a half sock with them, but I love them! Super comfortbale!
@Entangled: Hah I understand that :) They have a TON of color options. And the look of them online doesn't do them justice. I think they're cuter on...but I'm biased, since I love mine. They sell them at all sorts of stores, like Urban Outfitters, Nordstrom etc, so you could always try them!
For comfy shoes and boots, I love Naturalizer. They also have Wide and I tend to find heels there that I can walk around the city in all day. If you have an outlet mall nearby, I highly recommend their outlet store for great deals! I got a great pair of mary janeish heels last year that have an elastic panel under the buckle part (I love that it covers my socks) which sound like they would be perfect for you if they still make them.
Wow, I don't even know how to help you. Pretty much every shoe I walk in hurts after like an hour! I must not be supporting my arches enough. :(
OMG you guys are amazing. I am going to order a whole bunch of these and maybe the next time I go out, I won't have to be that girl in running shoes.
I also have to throw in a vote for Sperry's. I've worn these shoes almost every day (except in the summer) for two years, and they's held up so well. They're super comforable, and I love that I don't have to worry about sliding around on wet sidewalks. I love them so much that I bought fleece-lined ones for the winter! Mine have a red plaid pattern on the side instead of the purple pattern.
@bakerella: OK, I am giving in to the massive cuteness of the Jessica Simpson ballet flats. I know odds are high they'll fall right off my feet and I'll have to return them but they are too cute to resist!
I also ordered a pair of sperrys so we'll see how those go - they even had one of my favorite style/colors in wide at zappos. Though assuming the ballet flats don't work, I'm probably going to try one of the other suggestions, too. Seriously - so much amazing shoe advice on weddingbee. :-D
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I have shoe issues. Heels, flats, whatever... it doesn't matter, it seems like the only shoes that I can wear if I have to walk more than a block or two are my reefs and my mizunos. I'm really looking to change this and am looking for suggestions of either cute sneaker-ish shoes or comfortable non-sneakers that can take a mile or two of walking.
Any suggestions so I can stop being the girl with nice jeans and a sweater and raggedy old running shoes?