Little Reviews: Windy City Pin Up {Chicago}

A while back, I wanted to do something special for my husband for our 10th wedding anniversary. A talented friend had agreed to shoot a boudoir photo session for me, but I would have to figure out the outfits, the hair, the makeup and the poses myself.

After days and weeks biting my nails and scouring Pinterest, I lost my nerve.  I got scared. Overwhelmed.  Ashamed of my body.   I told myself I would take the leap only after I lost weight. That was almost three years ago…

Windy City Pin Up Chicago
Photo Credit: Windy City Pinup

Fast forward to 2016, the year I turned 40 and decided to start taking care of myself.  What I had not learned in the halcyon days of my misguided youth was that taking care of yourself has to begin with loving yourself first.  If I couldn’t love the body I was in right at that moment, how could I hope to give my body what it really needed, be that proper food, exercise or rest?  The way out of the cycle of self-doubt and self-harm was self-love.  So on my 40th Birthday, I decided to finally take that leap and give a gift to myself!

Windy City Pin Up Chicago
Photo Credit: Windy City Pin Up (Image has been edited for Little Lake County.)

Windy City Pin Up is “Vintage Inspired, Body Positive, Pin Up & Boudoir Photography”  owned and operated by Ashlee Dean Wells and her business partner Laura Wilson at their studio in Chicago’s Lakeview neighborhood.

Windy City Pin Up Chicago
Windy City Pin Up (L) Laura Wilson (R) Ashlee Dean Wells

On a typical day, I can be planning a PR event, a classroom party, my kids’ next team meeting and what to do with last night’s leftover chicken.  I have zero desire to plan one more thing.  So this time around, I wanted to go with a full-service studio that specialized in boudoir photography.

Windy City Pin Up Chicago
Laura Wilson touching up make up. Photo Source: Windy City Pin Up on Facebook

I didn’t want to think about what I would wear, where we would shoot or what to do with my hair. I wanted someone to do the heavy lifting whilst I reclined in a chaise, eating grapes Cleopatra-style and looking fabulous.

Windy City Pin Up offers an extensive vintage wardrobe with a full range of sizes.  Plus size ladies don’t have to settle for a few shapeless pieces.  At a size 20, I had enough stylish choices to make Joan from Mad Men envious.  And I wasn’t limited to the 50’s and 60’s eras.  You can relive the Jazz Age as a 1920’s flapper or roll up your sleeves like WWII icon Rosie the Riveter.

Windy City Pin Up Chicago
“We Can Do It!” Photo Credit: Windy City Pin Up

For an intimate photo session of this nature, I believe you pay as much for the experience as for the photos.   It’s an extremely vulnerable position to try to feel and look sexy in front of strangers.  Ashlee and Laura go out of their way to not only make you feel comfortable, but for you to enjoy the process as well.  It is like playing dress-up after all!

Windy City Pin Up Chicago
Photo Credit: Windy City Pin Up

For those who desire it, a pre-shoot consultation is included prior to your session.   You can peruse their wardrobe and try on outfits–don’t even worry about shoes and jewelry (but you should have your own hose and underwear!)  They’ll give you tips on how to prepare mentally and physically, like making sure you are well-rested and hydrated.  Laura works with you personally on different poses and will share the secret of the perfect camera smile.  She’ll even help you figure out how to wear a garter belt and attach your hose, because unless you’re a burlesque performer, you probably have no idea what you’re doing.

4th Trimester Bodies Project
Photo Credit: 4th Trimester Bodies Project

Now there are many places one can go for boudoir photography, but once I started searching I knew Windy City Pin Up was the only place I could go.  You see Ashlee and Laura are also the lovely souls behind the 4th Trimester Bodies Project, a nationwide photo documentary and movement to empower women.  Through photos and storytelling, Ashlee and Laura encourage women to embrace their postpartum bodies and reject a one-size-fits-all notion of beauty.  When I learned these were the same women, I did a giddy school-girl dance in my chair and knew I had to work with them.  (You can too during our Mama Strong event on February 18, 2017.)

Having worked with them, I know firsthand that “body positivity” isn’t just a buzzword or marketing gimmick.  They did honor to my 40-year-old body.   Ashlee will not employ extensive use of photoshop to reshape you into a different person.  How can one truly feel good about yourself, looking at photos of a person who doesn’t actually exist?  I needed a studio that would just  “get it.”  A place that wouldn’t think to question why a woman at her highest adult weight would dare try to memorialize her body with pin up photos.

Windy City Pin Up
Photo Credit: Windy City Pin Up (Image has been edited for Little Lake County.)

Besides all the kumbaya, self-love, mushy stuff, pin up is just plain fun!  If you have a sense of humor and don’t take yourself too seriously, it’s really an entertaining affair.  I wanted to go pin up style because, in my mind, boudoir is all about fantasy isn’t it?  No one really spends their days rolling around in pink satin sheets with camera-ready hair and makeup, batting our eyelashes and coquettishly biting a perfectly manicured index finger.  If I was going to do this I was going to have fun with it.  If I was going to play a role, I felt more comfortable playing Lucille Ball and Marilyn Monroe than Joan Collins or Kim Kardashian.

I also liked that during the pin up era, you didn’t necessarily need to be naked to be seductive.  Oh sure you can go full birthday suit at Windy City if you want to, but I wanted the chance to turn at least one image into a profile picture my mother could see.   Pin up can be just as titillating fully-clothed.

Windy City Pin Up Chicago
Photos by Windy City Pin Up

If you’re itching to take the plunge but would like the company of friends to boost your courage, Windy City Pin Up offers party packages!  It’s a unique option for a milestone birthday, bachelorette party or a “simply-because-you-deserve-it” celebration.

Windy City Pin Up Chicago
Bridal Party at Windy City Pin Up / Photo Credit: Windy City Pin Up

Windy City Pin Up isn’t just about the bedroom either.  You can book vintage-inspired family or Mommy & Me photo sessions too.  The even have in-house children’s wardrobe selections.

Windy City Pin Up Chicago
Family Photo Session / Photo Credit: Windy City Pin Up

Valentine’s Day is fast approaching, and while it may be too late to get pictures for your sweetie, consider treating yourself instead to a playful, empowering experience and timeless photos.  You can always give them to your significant other for your anniversary instead and just pretend you did it all for them {wink, wink.} I promise not to tell.

Windy City Pin Up Chicago
Photo Credit: Windy City Pin Up

Windy City Pin Up
Chicago | (347) 746-8792 | [email protected]
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Disclosure:  All thoughts and opinions are based on the author’s personal experience.  No financial consideration or compensation was provided to solicit this review. 

Windy City Pin Up is a featured partner in our upcoming Mama Strong event.  Tickets are $110 and available through Eventbrite.  Please visit our event announcement for full details. 


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About Loralie 264 Articles
When Loralie isn’t out exploring with her two pint-sized adventurers you’ll often find her in front of her computer plotting to take over the world (or at least Lake County.) She appreciates good friends, good food, expensive shoes and parents who make two lanes in the drop-off/pick-up line at school. Her spirit animal is The Hobbit. She invites you to join her on her quest for unique distractions, diversions and deliciousness in this county we call home. She is the Features Editor and Marketing Director at Little Lake County.

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