I Hired a Stylist to Reinvent My Wardrobe After Baby and Here’s What I Learned

First things first: Who am I fashion-wise? Jenny began our six-hour meeting with an interview. She asked me about my style problems (“to find clothes that fit, look good and can accommodate an impromptu nursing session”), my style icons (“a combination of Kate Middleton and Rose Byrne”) and my style goals (“to zero in on a uniform for work, but also find simple and minimalist options to make life just a little easier”). Most importantly, Jenny wanted to know: “How do you want to feel?” I was clear on that one: I wanted to feel relaxed, pulled together and approachable.

Next, it was time to see what we were working with. With the interview portion completed, we cracked open my closet doors, which is the sartorial equivalent of bearing your soul. What does my soul say? Well, it’s a hodge-podge mismatch of dry cleaner hangers (a big no-no, according to Jenny) and utter disorganization. Jenny reined in her judgment, and broke out some key supplies: non-slip hangers, sweater boxes and a shoe bag.

From there, we pulled each piece out one by one…by one. No joke, this was the bulk of our session. My closet isn’t massive, but somehow over the years I’ve managed to fit in so, so much. We piled every item high on the bed before Jenny held each piece up and asked me questions: “When is the last time you wore this?” “Does this item still fit?” “How do you feel when you wear this?” “Does this item still authentically represent your style?” Gone immediately were the things with even a tiny inkling of a stain. (If I know it’s there, will I ever reach for it in my closet? Nope.) Also, gone—my maternity clothes, which I’d been holding onto for frumpier-feeling days. “No sense in looking backward,” she said. (I set them aside for storage.) As for the stuff that doesn’t currently fit? This was actually the most emotional part. Every morning since my son was born, I open my closet and stare at my favorite pieces—a jumpsuit with a cinched waist; a cute, but now too-small floral dress I wore to my bridal shower. These things put me in a negative head space before I even walk out the door. Per Jenny, it’s OK that they don’t fit right now and not a reason to discard permanently. But as a kindness to myself, she asked me to tuck those items out of sight and revisit them in six months, once my body has further adjusted to being a mom.

About those A-line dresses… This was where Jenny really tuned into my goals. As we reviewed, it was clear: I have way too many dresses in this classic shape, but as we edited, it turned out that most were ones I never wear, specifically because they’re less forgiving of my new curves. As I continued organizing (sweaters are always folded and never hung; shirts on hangers are always buttoned all the way up), Jenny jotted down notes about what was missing. Mainly, dresses sans seams, chunky sweaters, midi skirts and more tops. (Yep, in my closet cleanout, I learned that I had a zillion dresses and bottoms, but only four truly wearable shirts.)

With everything sorted, we began rebuilding. When I say my bedroom was a disaster, it was a disaster. But, there was a light at the end of the tunnel. As we re-organized, I made several piles—one to donate, one to consign and one to trash (stained clothes are nobody’s friend). When we were finished, I had close to 70 percent of my wardrobe in bags and ready to get rid of. What was left behind were clothes about which I felt 100 percent confident. Better yet, my closet was no longer packed to the gills, meaning I could quickly see what worked together and get dressed on the fly.

New closet, new mom. Jenny reminded me of this throughout my session, but again as we parted ways: “Sorting and re-organizing your closet is one of the biggest acts of self-care you can give yourself—especially when you’re a new mom.” I’ve felt the effects of that statement ever since. Purging and re-organizing was empowering but also identity-driven: It helped me remember who I was before my son, but also helped me move on to who I am now and who I’ll be next. Of course it’s fun to keep some things that remind me of the past (hello, the halter dress I wore for my final a cappella concert in college), but as Jenny said, “Why work backward?” I’m different now—both physically and emotionally. I also need to go shopping.