I Got a Professional Fashion Makeover in Boston!

“You’ve got to tell me how your professional fashion makeover went!” friends demanded since they learned I’d booked a company called Stilista Boston to save my ailing style.

“I mean, what did the fashion consultant do?” they pried. “Did she make fun of your clown-like shoes? Did she throw that hideous orange shirt out the window? Did she burn that ragged brown cardigan?” (Sheesh — clearly I wasn’t the only one who knew I needed some fashion resuscitation.)

Given how great my experience was with Stilista, I’m going to tell the whole story here, since it was so different from how I’d feared it would be.

The story starts earlier this year when I received an email from a woman named Maria who I’d gone to high school with years ago. “I saw your article about travel fashion as a new mother,” Maria wrote, “and I realized you might be interested in trying out the styling services offered by my company, Stilista.”

“Oh!” I replied. “Well, I do have a closet full of decade-old, ratty clothes that don’t fit me… but I’m nervous! I mean, will you make fun of me when you open the closet doors? Will you force me to buy weird ‘Dry Clean Only’ stuff that I’ll never wear? Will you judge me because I don’t wear makeup?”

Maria assuaged my fears, so I went ahead and booked her for the “Turn It Around: Wardrobe Revamp“ package: An Initial Consultation, a complete Wardrobe Analysis, and (on a separate day) a three hour shopping trip.

The Initial Consultation made me feel much better. For an hour, Maria asked some excellent questions about my style preferences, and I vented all my fashion neuroses to her, telling her some things I’ve never told anyone. She listened and took notes, and I got more and more animated as I revealed my style agonies. “For some reason,” I confessed, “I can spend $500 on a plane ticket, no problem, but it physically hurts me to pay more than $12 for a shirt!”

Maria nodded, understanding. “Our fashion purchasing patterns run very deep,” she said, making me feel like far less of a freak.

“Yes!” I blurted out. “I was raised to be thrifty, and loved wearing my cousins’ secondhand clothes, and so that mindset is just what feels right, now. I get most of my clothing now for free from clothing swaps, but given that I’m now a 32-year-old professional and mother, I really want to step it up more… but I don’t know how! I get into a department store and I just panic.”

“Our shopping trip will help with that,” Maria explained. “We can work within your budget, and once you have a few high quality, versatile items, getting dressed will be so much easier. Just like you plan for travel, it helps to plan for shopping. We will go in with a clear list that we make together after the Wardrobe Analysis. Speaking of that, shall we go upstairs to your closet for the next part?”

The Wardrobe Analysis was awesome. We went through every single item of clothing that I own (including all shoes and coats), and Maria didn’t once make fun of me, even as it became clear that I owned some truly tragic fashion situations.

My first favorite moment came when Maria asked, “Do you mind if I organize your closet?” I gaped at her, then at the balled up wads of clothing strewn inside out, four-to-a-hanger. “Um, go ahead… I beg of you!” I replied.

My other favorite moment came when I held up a threadbare shirt that I’d gotten secondhand in college over a decade ago. “Should I keep this?” I asked Maria.

“Well,” Maria replied tactfully, “In our Initial Consultation you explained that you don’t like frayed or tattered styles. This shirt is in that territory, isn’t it?”

Thanks to Maria’s respectful coaching, I was able to make a pile labeled “Clothes to Donate” that was so large, I could completely bury my body under it (as evidenced by the second photo). Once the bag was donated, I was hit by how much lighter and happier I felt. It was akin to the exhilarating freedom and simplicity that comes from backpacking around the world and realizing all you really need are a handful of great clothes.

The Three Hour Shopping Trip was two weeks later due to my travel schedule, and Maria meticulously planned it. She had emailed me a three page document detailing my style preferences from our Initial Consultation and Wardrobe Analysis, and it included a clear shopping list. For items that we would be unlikely to find in stores (namely cute comfort shoes for my rather expansive feet) Maria provided web links for where to purchase quality versions online.

We met in the discount wing of a big department store, since Maria wanted to respect my lower budget, but to also explore some non-secondhand stores that I’d never before entered. As I walked up to meet her, she handed me a coffee. Bliss! I calmed down from the tizzy that department stores usually send me into, and followed Maria, awe-struck, as she systematically gathered items from our list off the shelves and into the cart.

“Of course,” she said, “just like in the Wardrobe Analysis, feel free to push back if you disagree with anything I suggest. You have to actually want to wear anything we get!”

In the Fitting Room, we took two stalls next to each other and Maria handed me clothes as I popped out and modeled them. The skin-tight fuchsia jeans (my idea) were a “No,” but eight other items in that first store were a “Yes.” That was a miracle, as was the fact that Maria’s calm presence meant that I actually followed through with the purchases rather than bolting out of the store and back on the train as I so often do when shopping panic hits me.

We hit three more stores after that: an inexpensive but fashionable one, a high end one (that freaked me out so blatantly that Maria guided me to the exit), and a fancy secondhand store. About an hour in, I was getting visibly fatigued… when suddenly Maria pulled a water bottle out of her bag for me! I gulped it down, and she revealed that she had another water, plus a granola bar packed for me, too, should I need it. What service!

The result of our three hours of shopping? Fifteen items from our shopping list for less than two hundred dollars. Nearly everything ended up being on sale! The items were a great mix of basic essentials to replace the ones I’d worn to threads in my closet (tanks, work pants, tights) plus fun pieces to add flair (like the fabulous print pencil skirt in the first “After” photo).

Throughout our shopping, Maria gave tips on how to select a fit, brand, style, and color, and answered all the deep, dark fashion queries I’ve been too scared to ask, like, “Are these pants scandalously tight, or perfectly fitting?” and “Would it be bad to wear a knit cardigan to my friend’s wedding?”

A few days after our shopping trip, Maria emailed me a detailed follow-up document that summarized the shopping list items I still needed to pick up to round out my wardrobe. She provided names of good stores and websites for each. I’ll do that last bit of shopping myself this weekend before my teaching job starts up again, and will sail into the school year in fashionable ease!

In Conclusion, Maria really helped me expand my clothing choices and understanding, but she also gave me something unexpected. I now have more confidence in my own fashion choices! My expectation of a professional fashion consultation was that I would be told I have horrible taste and needed a sartorial brain reboot.

Instead, it was deeply reassuring during my Stilista experience to have a professional tell me that over half of the wardrobe I already own is actually great (even a few pieces I have been unsure about), and to see that many of the items Maria picked out for me in the stores were the very ones I would have selected myself. I’m on the right track!

If you look at photos of me in middle school, you’ll see that I spent much of my life being ashamed and unsure of my fashion style. How beautiful that someone from my past emerged to bring closure to those worries!

I was provided with much-needed fashion help by Stilista Boston, but all opinions and swimming around in piles of clothing are my own.