I Need Fashion Advice

I haven't lived in Chicago for a while, so I"m sure you'll get better responses from others who currently live there, but honestly, it's either cold or blazing hot! So, bring layers. This summer, after June, it will be hot. If you're going in June, you never know what you'll get. Good walking shoes are a must. I think tennis shoes are great, but I'm just as comfy walking around in my Teva flip flops as anything else. I think it depends on what you're comfortable in. The city blocks are long and it's just pavement so it can be hard on the feet and knees after a while. It's a great city though and tons of fun...plus the food is generally amazing! There are a lot of good dive type places as well as some super amazing chefs that own restaurants there! Have fun!

Well, you are going to need three sets of outfits: 1)morning (casual like jeans and blouse or capri pants and a shirt- - NO flipflops and NO T-shirts)
2) afternoon (colorful casual dress or casual skirt+blouse/shirt even polo shirt); 3) evening (cocktail dress or even a simple little black dress).
SHOES: for 1) comfy sandals (flat ok but not ugly like the Birkenstock or whatever they are called, just HORRIBLE)
for 2) flat ok again but a little more feminine in shape or materials; for 3) definitely high (or higher) heels and feminine shape (NO round toe). You are going to be fab!!

This season they have the most adorable sun dresses in different lenghts. A tailored solid jacket is perfect for the dresses. You can never go wrong with a pair of white capris. A lovely silky top with a solid shell under.

As for shoes, I simply love wedge heels. They are stylish and comfy. This season's flats are cute, cute, cute too. You can't go wrong with a solid peep toe flat. Where to buy these your can go anywhere. I know you are staying at a 5 star hotel so you should probably splurge in the handbag area. One small handbag and one supersized handbag would be perfect for your trip.

Have fun trying on different things and look at yourself in a full length mirror. It helps to get a full look at yourself. Enjoy and have fun fashionista.

I 100% agree, layers are the way to go. Especially downtown, because the breeze off the lake coupled with the shadows from the buildings can make an otherwise hot day seem chilly at times. Definitely bring some good, comfortable walking shoes if you plan on doing a lot of walking.