Chicago Street Fashion - Naomi

I spotted Naomi yesterday in the Loop looking all saucy in this neutral one piece.

Nice work lady!

Shaun Sperling of Madonna Bar Mitzvah Fame

The last time I saw Shaun Sperling he was dancing the Horah at my sister Rachel's wedding to the tune of Havah Nagila and then later on bumping and grinding to Prince.  So when I saw the video of his Madonna themed Bar Mitzvah from 1992 surface on the internet his smooth moves didn't surprise me at all. What was surprising is that since the video was posted to Youtube almost 1 million people have watched it and it's landed him on The Today Show, Jimmy Kimmel, Perez Hilton, and many more.

20 years later,  Shaun Sperling is a Lawyer that lives with his delightful partner Matt Leyes here in Chicago. 

I couldn't help doing a little photoshop magic to bring back the AMAZING Madonna shirt that Shaun's mother had airbrushed for him to wear under his suit while reading the Torah and for the BIG reveal for his surprise performance.

If you haven't seen the video yet, I guarantee it will make you smile...

Chicago Street Fashion - Azeeza Khan

Designer Azeeza Khan (nèe Desai) of Atelier AZZA is back! Wearing an outrageously cool scarf over basics, all of her own design.

Azeeza and Atelier Azza  were featured in my Designer Spotlight Series last month. I spoke with her about work and life here in Chicago. See what she's wearing (spoiler alert: it's totally amazing) and read the interview here.

Chicago Street Fashion - Amy

Lovely Amy works at Marc Jacobs in the Gold Coast (which PS ladies, is having a 70% off sale at the moment.) She looks resplendent here in gold and mustard. Loving the pop of red from her loafers.

Gilt City Lollapalooza Pool Party

This past weekend Gilt City Chicago threw a fabulous Lollapalooza pool party in downtown Chicago. The shindig was packed with stylish babes, like Shannon O'Brien, woman of a 1000 looks. I swear, every time I see this girl she looks completely different (and amazing!).

Jenn Lake is the vice president of Zapwater PR and an all around glamour girl. I love this dress by Three Floor and her Dries Van Noten shoes. Lookin' lovely as always.

I love Katie's lace ensemble, SO COOL.

Lollapalooza 2012 - Cheyenne Meets Chanel

I caught up with Shea Marie of the blog Cheyenne Meets Chanel at Lollapalooza this past weekend. She looks glamorous and rocker chic as per usual.  Loving her rag tag cheetah print shorts with this brown belt.

Lollapalooza 2012 - Festival Babes

Beautiful Aaliyah, who I survived the crazy storm with, looks overjoyed t o be back at the fest.

Theresa DeMaria is wearing the perfect festival outfit, so perfect it looks like it may have been put together by a professional stylist. Well surprise, surprise, that's exactly what she is, for Factor Artists here in Chicago.

This pair looks so cool. I love the woman on the right with her tricky halter using a Hermes scarf. FANCY!

Maryam Moma looks incredible here in her vintage USA bralette and Prada bag.

It wouldn't be festival season in Chicago without an April Francis sighting. Three rad things about this outfit are 1. She's a mobile music machine with her Jammy Pack 2. Those are no oridinary galoshes, they are Chloe dahling 3. You can't really see it but that's a Totes Dose Market bag.

Vintage camera as an accessory? Yes please!

Courtney Wachs looks awesome here in these heart shaped frames.

Lollapalooza 2012 - Lust For Life

Has anyone ever looked more ready to rock than Olivia Lopez of the blog Lust for Life? This is such a great festival look, nicely done lady.

Lollapalooza 2012 - Festival of Style

So much great style this year at Lollapalooza, despite the crazy weather which included sweltering heat and an INSANE storm that actually closed down the festival for several hours people really brought their A-game.

Jena of ChiCity Fashion looks fantastic with her clear purse, rad belt and positive attitude :)

I love these flowers musician Alexandra Lawn pinned in her hair.

Jennifer Worman of Red Soles Red Wine looks cute as a button outside the Gilt Lollapalooza Pool Party.

How did this guy get a bike in?! My dogs are still barking from the fest, this would have been a dynamite mode of transporation for me. Maybe I'll try and finagle something for next year!

Caylee of the blog If You Seek Style looks lovely in her crazy aviator sunglasses.

But wait, there's more! Be on the look out all week for tons more Lollapalooza 2012 festival styles.

Lollapalooza 2012 - Claire Van Eijk

I love this photo of Claire Van Eijk. The way the colors of the background compliment her blue faux hawk is incredibly pleasing to me also her ear/nose ring is AMAZING. These are some cool things I know about Claire; she has a rad tumbler called Planet Claire, she's a backup dancer for Grimes when she rolls into town, and she's wearing a sweet necklace from Emerging Thoughts.

Look for more Lollapalooza 2012 street style in the coming days.

Lollapalooza 2012 - The Dum Dum Girls

One of my favorite performances of Lollapalooza this year was The Dum Dum Girls. They absolutely killed their performance on Sunday and were without a doubt the most stylish act at the festival. I caught up with lead singer Kristen Gundred and drummer Sandy Vu as they were signing autographs for two very sweet little girls at the request of their father (congrats pops, you're the coolest dad ever).

Kristen and Sandy lookin' all 60's punk glam here. I love Kristen's iconic striped tights, which she also sports in their video Bedroom Eyes (see below).

Can you say ROCK GODDESS?! Scott Drasler of Partyline Chicago snapped these great shots of Kristen and Jules in action. Check out more of his Lollapalooza 2012 snaps here.

Like what you see and hear? You can go download their latest track 'Lord Knows' for free on their website, SWEET!

Lollapalooza 2012 First Look

Lollapalooza Day 1, you were a rollercoaster of emotions. VERY hot, very fun, and very exhausting due to the insane amount of stylish thangs I documented. Here is a lil taste to whet your whistle.

Matt Devine, the lead singer of the band Kill Hannah looks devine (see what I did there) AND totally pumped thanks to a little Red Bull action.

Sarah Ditty is one of the hot dancers from the rad band Totally Enormous Extinct Dinosaurs that tore up the stage to today at the fest.

Be sure to check back in the coming days for tons more festival style from Lollapalooza 2012.

Lollapalooza Style Flash Back

ZOMG Lollapalooza 2012 is this weekend! I've been looking at all the styley peeps I captured last year at the festival and thought I'd post some of the best looks to inspire your fabulous ensembles this year. I'll be at Grant Park all weekend shooting street style so if you want your photo taken tweet at me @tresawesome.

See you at Grant Park!