"You dress simply." - In Chicago

It's no secret I'm not big on "statement" pieces. I prefer subtle jewelry and I'm not much of a prints (large or small) person either. And oh gosh, I so do not like peplum. (Wait, what does that have to do with anything? Yeah nevermind.)

So it should've come as no surprise when, on a water taxi ride back to downtown Chicago - with a 9-year-old I have no relation to (the daughter of a friends' sister) said to me, very matter-of-factly "You dress simply." To which I replied, "Yes I do."

I've always admired those folks who can legitimately pull together an outfit with just a white or black t-shirt, jeans and some really awesome jewelry. Not even saying "over the top" type jewelry - just....you know...elegant. (Boy I hate that word. In the design world "elegant" is thrown around like the old family pigskin. "I want it to be elegant!"Loses some of its oomph after you've heard it the 6,5234,898th time.) I just wanted to look halfway decent out in the "big city."Anyway! Fabulous Florida Mommy put together a whole post on "P is for Plain White Tee" and Jenna Lyons claims she loves to wear Hanes Mens White Tees (I can't find this reference, it might've been tank tops...). So me, with a multitude of J.Crew tees (in Vintage Cotton, Tissue and my special J.Crew Collection Modal Tees) - I can easily pull off the casual tried-without-trying look, right?

Here's an example oh how I wanted to look, pulled from Pinterest:

Well I did try, really I did. But I still looked like a schlub. My t-shirts never fit quite right - oh they're the right size (I mean, in theory I thought they were the right size), but they end up being too long, or lumpy in odd places. Or just saggy. They never look polished. I did attempt to pair the simple white tees with "nice" jewelry. I'd just purchased a Lauren Wolf Multi-Strand Turquoise Bead & Silver Bracelet and I had a few bangles from Low Luv by Erin Wasson (all purchased from Gilt.)

Multi-Strand Turquoise Bead & Silver Bracelet by Lauren Wolf Jewelry

But despite my best efforts, I just looked like a ruffigan wearing the odd bracelet or three (I still haven't quite gotten the hang of the arm party yet either). It is what it is.

After visiting a non-Magnificent-Mile Starbucks on Sunday morning, I returned to the hotel and explained to my husband that all the people there (who I'm totally assuming to be locals, in large part because many of them had dogs and it didn't make sense in my head that they would be at a coffeeshop from out of town with your dog in tow) - were wearing t-shirts, jeans and flip flops! They actually did look like they'd just rolled out of bed on a weekend morning and ran out for coffee. But their version of "oh I just threw something on" looked SO much better than my "I totally contemplated what to wear and changed three times before I left the hotel" style. They all looked so nice and put together. How do they do it?

My husband's response? "Money. They have lots of money."

So yeah, if we're being honest - if you're able to afford an apartment or condo in that part of downtown Chicago, you're probably not too bad off (if I were to count other peoples' money, which I'm totally doing.) But - true or not - it's my belief that if you've selected the proper fit and style you can look pretty darn polished in anything - be it the $84 plain white t-shirt from Steven Alan, or the $5 shirt you found on clearance at H&M. I want to believe that. I need to believe that. Because I just can't ever see myself spending $305 on a long-sleeved plain white t-shirt from Net-a-Porter (just you wait, I bet I'll eat my words one day.)

'Lest you think all I can do is whine about my inability to get dressed while on vacation (hey, it does seem to be a recurring theme when I go out of town) here are a few shots of Chicago. :)

Walking along Michigan Avenue

Walking along Michigan Avenue (other side of the street)

Dinner on the patio at Giordano's

Walking through Lincoln Park

Dinner at Nacional 27

Afternoon in Chinatown

Docent tour of the Aragon Ballroom

Drinks at the Green Mill Cocktail Lounge

A quick stop by Permanent Records
(Bob Pollard of Guided By Voices gave a shout-out to Permanent Records during The Metro show we'd attended the night before. For the record, GBV = not for me. Now I know.)

Caught 'The Queen of Versailles" at the Music Box Theater

Red Line Back to Downtown

And here's the Polyvore of what I packed. There were a few things I didn't wear, like the Mona Printed Pumps - mostly because of all the walking......and the places we visited on this trip didn't really call for heels.

Chicago: August 2012 by jaynawallace featuring v neck t shirts

J.Crew v neck tee / J.Crew knit top / J.Crew heather t shirt / J.Crew boat neck sweater / J.Crew v neck t shirt / Madewell linen top / Madewell oversized top / Madewell knit top / Madewell black t shirt / Madewell striped top / J crew / J.Crew high waisted denim pants / J.Crew j crew shoes / J.Crew j crew shoes / J.Crew round toe pumps / J.Crew j crew jewelry / J.Crew chain necklace / J.Crew buckle jewelry / Madewell metal jewelry / LowLuv bronze jewelry / Madewell engraved jewelry / Madewell beaded jewelry / Madewell vintage style jewelry / Madewell friendship bracelet / Madewell stud earrings / Diamond necklace / J.Crew indian shawl / American Vintage scarve, $62 / Miansai® rope bracelet / Berkshire Road Lori

So there you have it. To recap, Chicago was a blast, as always. And, in that I was actually out in the real world for a few days, I've come to the conclusion that I would like to dress "simply" without being "simple." How does one do that, exactly? I'm open to tips.