What to Wear? Chicago

Should I Wear This?


Tomorrow, I'm taking my family to Chicago, where we'll be visiting a major corporation's headquarters for a three-day family getaway.

My longtime blogging BFF will be there, as well as other bloggers I absolutely adore, so as you can imagine, I'm excited!

BUT! Lots of pictures will be taken, so ...

I'm scared!

Because this means I have to put some thought into what to wear.

Ordinarily when I'm going on a trip like this, I take a few minutes to try on potential outfits. This time, I thought I'd involve you in the process.

I need three or four ultra-casual family picnic-style looks for this trip.

Check out the photos in this post and tell me your faves, because I'm having some trouble deciding!


Readers, don't fail me now!







I just got this Ann Taylor dress for my birthday from my in-laws. They have great taste, don't they? That's because I went to the mall myself this year and picked out my own presents! Heh. Anyway, it was $49.99 down from $158, so I was very pleased with the find.

I love it, it's very comfortable and cool. It's also silk, though, and in a family activities/barbecue setting, I'm a little bit concerned about such delicate material.


I love the polka dot shirt and J.Crew Minnie pants in the first picture, but that's about the only pants outfit I have that makes me feel casually glamorous. I'm just not a pants girl. This was the other outfit I came up with -- Gap skinny jeans and a shirt that I love, but that's three years old. I'm not feeling ultra-confident about this one.


I almost forgot about this dress, but now that I've tried it on, I think it's a shoo-in. It's comfortable, knit, long enough to chase the kids in without worrying about wardrobe malfunctions, and it won't wrinkle too badly in my luggage. What do you think?


This Calvin Klein dress just screams picnic to me. It's a very thin, billowy cotton material and it feels so Mad Men, I can't stand it! Hmmmmmm.

This dress is simple and casual and washable and non-wrinklable. The only problem? I, um, wore it at BlogHer last year, so IT'S ALREADY BEEN SEEN (GASP?!).

However, I do feel really comfortable and confident in it, so ... maybe?

Your turn readers? Which looks are your favorite? Which would you leave behind?

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