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What shoes to wear?

Madison, WI
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10 posts
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What shoes to wear?

The posts have some strong opinions on what footwear tourists should avoid. If I shouldn't wear flipflops or tennis shoes, and I'm not going to wear heels, what does that leave?

Here's where we'll be going: Field Museum & Shedd Aquarium, Art Institute, Lincoln Park Zoo, and I want to do shopping in the Bucktown/Wicker Park area. Restaurant-wise, I'm still researching to find places with fantastic food, but where (nice) jeans are perfectly acceptable.

I'm female, but (horror of horrors) I don't own that many shoes, just Birkenstocks, dressy heels for work, and tennis shoes.

Any suggestions for fashionable, yet comfortable shoes?

Chicago, IL
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1. Re: What shoes to wear?

Honestly you should wear whatever you feel comfortable in, there are a few restaurants with strict dress codes but unless you are planning on dropping several hundred dollars on dinner, I don't know that it matters what is on your feet. The only other place that you might need dressier shoes is certain nightclubs and piano bars. Why try and buy new shoes before you travel? You're just asking for miserable feet.

I live in sandals during the summer, no one has shunned me or ridiculed me yet. And if they did I certainly wouldn't care.

Destination Expert
for South Haven
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2. Re: What shoes to wear?

i have what i consider pretty ugly but oh so comfortable sandals that are my chicago shoes....any time i switch (once to cute wedgies and once to adorable sky high flip flops) i suffer for days!! not worth it....i'l wear my comfy sandals and the heck with it!! I can't remember where i bought em but they were pretty cheap and i got 2 sets so when one wears out i'm still in business....they work great at disney also!

and i've never been shunned from anything!

Ann Arbor, Michigan
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670 posts
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3. Re: What shoes to wear?

I agree, go for comfortable sandals or anything else you like. If you do choose a dressier venue for evening, change shoes just before you go.

I've worn flip-flops, hiking sandals (Chacos, etc.), tennis shoes, crocs, slip-on moc-type shoes from Lands End, fashion sneakers (like from Skechers or Rocket Dog) and probably any number of other shoes. No one else will be looking at your feet.

chicago, il
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196 posts
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4. Re: What shoes to wear?

Dear Shuk9:

I have not read the posts that have strong opinions on what footwear tourists should wear...but why should tourists be any different than your average Chicagoan? Wear what is comfortable. I live in the suburbs, but have lots of friends who live in the city, and I know I have seen them wear flipflops and tennis shoes at one time or another!

I agree with the above posters. Unless you are going to an upscale restaurant with a dress code...wear what is comfortable for you!


Destination Expert
for Nile River Valley
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12,817 posts
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5. Re: What shoes to wear?

We also get people on the London forum with strange ideas about shoes. The answer here is the same - if you are going to do a lot of walking, wear whatever is comfortable for you. I'm going to Chicago shortly and expect to do just that. It will be obvious that I am a tourist and have been walking around a lot. Any restaurant that turns me away on that basis is not one I want to go to!

Pittsburgh, PA
Destination Expert
for Pittsburgh
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1,135 posts
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6. Re: What shoes to wear?

You can search www.zappos.com for shoes according to type, heel height, etc. and then read the reviews to see how buyers liked the shoes. I was reluctant to order shoes online until I realized that zappos (and some other shoe sites too) have free shipping both ways. Order two sizes if you're not sure which will work. Zappos will deliver shoes within hours of your order, which is satisfying.

As to brands, Dansko, Ecco, & Merrill have comfortable sandals. They're still clunky looking but have some pretense to style and are super comfortable for city walking.

Good luck. The right shoe can make all the difference!

Rensselaer, Indiana
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8,357 posts
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7. Re: What shoes to wear?

Not to put a different spin on this subject, but I happened to be on the Lakefront Trail quite a bit this past weekend and saw a couple of ladies walking gingerly in heels there. This was in the morning and middle of the day - not in the evening or night. Now, *that* was inappropriate shoe attire!

The bottom line is to wear the appropriate shoes for your activity. If you are going to do a lot of walking, wear comfortable walking shoes. If you are going out for dinner to a nicer place, then you shouldn't be wearing tennis shoes.

I wouldn't recommend wearing new shoes (not yet broken in) - that is, not unless you want to spend some extra $ for bandages - because Chicago is a walking town.

Sydney, Australia
Destination Expert
for Sydney, Uluru-Kata Tjuta National Park, Business Travel, New South Wales
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8. Re: What shoes to wear?

One thing I remember about Chicago was "Not" having comfortable walking shoes with me..Its a city that lends itself to walking, especially if you enjoy shopping.

The shops are awesome in Chicago and found them to be better than Paris...everyday, I returned back to my hotel with aching feet..and a handful of shopping bags. !! minus any comfortable shoes..too many other wonderful items to buy..

Take comfortable shoes / and one pair of dress up shoes for the evenings.

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Chicago, Illinois
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297 posts
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9. Re: What shoes to wear?

For the itinerary you've outlined, tennis shoes, flip flops, Birkenstocks, jeans and shorts would be just fine.

I've lived in the Chicago area all my life, and I would feel both comfortable and appropriate in any of these. Now, I probably wouldn't wear my gym shoes to the Everest Room, but they'd be fine in many restaurants and definitely at all of the places you list in your opening post.

Chicago, Illinois
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7 posts
40 reviews
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10. Re: What shoes to wear?

Wear comfortable shoes when you're out and about, but pack a pair of shoes that work at a nice restaurant.

Do NOT wear flip flops unless you don't care about what your feet touch - think about subways/els, the street, peoples stepping on you...

If you wear heels - take a taxi. If you stay downtown, it's a $10 (max) trip to the best restaurants - think of Sex and the City - "Taxi Heels".

Nothing worse than seeing a couple dressed to the nines walking - with the poor woman in high heels - because the man wanted to save a few bucks! Hey, you're here - live the life!