I Hired a Personal Stylist (in Milan!) for My 40th Birthday

With 40 on the horizon, I decided that I am no longer available for my own self-neglect.

I’ve decided that I care. I’ve decided that I matter. That how I look matters. That how I carry myself matters.

And I deserve to look and feel my best – always.

Ahhhh, I turn 40 in two weeks!

Where did the time go? It feels like just yesterday I was racing home to watch “Total Request Live” on MTV or excitedly flipping through the latest edition of Cosmo Girl magazine. 

There’s a lot of nostalgia I still hold about my younger years – even my 20s and 30s – but there’s even more of it that I’m ready to let go of too. 

Honestly, that’s been the theme of the last year for me – releasing things that just don’t serve me any more: limiting beliefs, outdated ideologies, social conditioning. As I enter my 40s, I feel like I am shedding parts of myself in favor of a truer, more authentic version.

At the start of the year, I made a decision to treat myself more kindly and with more love: to get my body in its best shape; heal my gut; and revamp my style (more on that below). 

And let me tell you, it has been a journey getting to this point…

A New Narrative

I spent decades hating myself – everything from the way I looked to the way that I dressed; the scrutiny was even worse when I was in high school and weighed 200+ lbs. 

Over the last 20 years, I’ve lost (and gained) weight more times than I can count. I’d always white-knuckle it by beating my body into submission – usually by starving myself or working out like a madwoman (hating every square inch of myself along the way).

Then the pandemic hit and I gained 30 pounds that I haven’t quite shaken yet. As a result, I’ve lived in activewear almost exclusively, having never really returned to the pre-pandemic world of zippers and buttons; elastic everything has reigned supreme.

The truth is, I let go of myself, rationalizing my look with, “Who cares?” and my favorite, “What?? Leggings are pants nowadays.” 🤷🏽‍♀️

But with 40 on the horizon, I’ve decided that I am no longer available for my own self-neglect. I’ve decided that I care. I’ve decided that I matter. That how I look matters. That how I carry myself matters. And I deserve to look and feel my best – always.

New Decade, New Style

For the very first time in my life, I am putting myself first – unapologetically. My intention is to enter this decade as a brand new me. I am ready to step into the woman I was always meant to be.

I had already planned to go to Milan (and Lake Como) for my 40th birthday but as I thought about how I wanted to enter this new decade, I knew I needed a style overhaul. And where better to overhaul my style than in one of the world’s fashion capitals?

I found my personal stylist, Alessandra Benedetto through a series of fortunate events and was instantly enamored by her aesthetic; she embodied what I wanted for myself. After I reached out, we nailed the date of our shopping experience then scheduled a call to get to know each other and talk about my style goals (and yes, if you’re wondering, she speaks English).

Leading up to our Zoom session, I was taken aback by how nervous I was; I’d never done anything like this before! Immediately, however, Alessandra put me at ease with her warmth and charm. What I appreciated most was that she really seemed to understand what I wanted to achieve (a timeless and sophisticated wardrobe), plus asked great questions (e.g., “What emotions do you want to experience with your new look? What would you like your new look to convey about you to others?,” etc.).

Growth

I walked away from the call wanting to do cartwheels! I am so grateful I get to work with her. Right after the call, I started telling my husband all about it when suddenly – literally out of nowhere – I started crying; like an uncontrollable ugly cry.

What I realized is that for years, I’ve played small – belittling myself and marginalizing my own needs. The weight (and leggings) kept me hidden; they kept me safe. And now, here I am, ready to show up for myself. The emotion I experienced came from the friction of where I am and where I am going.

I may shed a few tears on my shopping day (which I already warned Alessandra about, lol) but I welcome them. No, I won’t be a size 2 but that’s ok; I don’t need to be one to “deserve” the experience. I deserve it simply because I owe it to myself to look the best I’ve ever looked and love myself more than I ever have.

And I am doing just that.