Cakestyle: The perks of using a stylist

At the Cakestyle loft. Isn't this purple dress hot?

For the first time in my life, I found out what it's like to have a stylist dress me. After attending a VIP reception at Cakestyle's Chicago headquarters, Kate and I booked an appointment with one of the company's lead stylists, Kaitland.

I love this Tracy Reese skirt

Since it is primarily an e-commerce company, a typical Cakestyle customer fills out a detailed survey online and shares her measurements and fashion needs. Then a stylist prepares a box of 4-5 outfits and drops it in the mail quarterly, along with a video on how to put together each of the included looks. The shopper returns anything she doesn't love using a pre-paid label and pays retail for anything she keeps. And that's designer retail, comparable to the prices you'd find at Nordstorm or Bloomingdales, not Macy's or Ann Taylor Loft. A typical box can cost about $2000--definitely outside of my budget!

Chicago customers get the personal treatment and can meet with their stylist personally at the Cakestyle loft in River North. Kate and I arrived at the space (just down the street from Nordstrom) with her mom, Carter, just after work last week. Kaitlin had refreshments laid out, a rack filled with hand-selected clothes and a large curtained dressing room. It was immediately obvious she'd put my stuff on the left and Kate's on the right, but because we wear roughly the same size, we were encouraged to cross-pollinate.

Trina Turk belted skirt

And that's when I learned what a joy it is to be styled. Everything I tried on fit. Perfectly.

Kaitland channeled my kinda sort of mod/boho fashion sense and picked out 5 dresses I desperately wanted to own (I purchased one). She found me a pair of straight-legged Paige jeans that made me look skinny, a mod silk tunic dress like nothing I've ever owned (and that I wish I'd bought) and suggested a turquoise skinny belt for the red and white Boden frock I'd arrived in. I felt so pretty and slim because everything I tried on was so flattering

The 60s inspired Milly dress I bought

Kate, who was down with the idea of outsourcing her lawyerly work wardrobe from the moment she met Kait at the reception, was similarly thrilled with her selections. She went home with a couple of dresses, a bracelet and a fitted cardigan. And it didn't hurt that Kate's mother was enthusiastic about everything we tried on, encouraging us with calls of "It's gorgeous! You should get it!"

I can't say enough about how pleasant the shopping experience was. I tend to get overwhelmed by options when shopping and I don't know where to look. I'm not familiar enough with labels to know my size in each one and too often I default to expected online stores that stock my style (Modcloth and Boden, for example). No one has ever told me how to belt, wear a scarf or pair the right shoes or boots with an outfit, so it's all trial and error for me. Having Kait explain the shoe and accessory options for each ensemble was key--especially because she was so low-key and never tried to sell anything. She just let the mirror do its work.

Would I shop Cakestyle again? Yes, but I'd feel guilty and a little self-conscious about my budget. I'd love it if Cakestyle could find a way to offer the same service at slightly lower price-points, or even point me in the direction of new labels and brands that might appeal to me. In the meantime, I'm browsing online and checking out my closet with "What would Kait think?" running through my head.