When I first moved out on my own after separating from my ex-husband, I looked into my new closet and suddenly none of my clothes felt like who I wanted to be anymore. I was a single woman now, working at a new job, and starting to date.


I was a fashion stylist, yet my closet was full of things that I bought because I needed something in a rush, leftover items from photo shoots, and things my ex picked out for me. I was terrible at letting myself buy clothes for myself. Now, nothing in there felt like me. The new position I had started post-divorce was as an Art Director on photo shoots and I needed to dress the part. I wanted to project myself as someone who was confident and an authority even if I didn’t feel that way. Fake it ‘til you make it as they say.

I felt I needed a fresh look as I started dating after divorce.


As a newly single woman out in the dating pool again, I wanted to feel confident and sexy in what I was wearing. Something I hadn’t felt in years and years. Probably more than a decade. But I sure was ready to change that.

I was taking on two brand new roles in my life and I needed to refresh my wardrobe situation and fast. So, I invited my friend (also a stylist) to come over and help me do a deep dive closet cleanse. At the time I didn’t realize what a momentous few hours this would be for me. I just thought I was doing what I usually do with clients, but for myself. But it was so much more than that for me. I took every piece and thought about how I felt wearing it. Did it make me feel good? Was I excited to walk out the door wearing it? There were so many pieces that just made me feel bad about myself. I tossed them into the giveaway pile and didn’t look back.

This process was my steppingstone to starting new. I was revamping my style and revamping my confidence level. I needed to figure out what the “new me” wanted to wear. I wanted to choose pieces that felt aligned with the new me who was slowly coming to life. And this new me was now ready to go out and buy just a few new pieces that added to my new life—pieces that really made me shine. What I chose was a fantastic pair of jeans that fit me just right and a couple of new sexy sweaters (it was January) to wear as I embarked on dating after divorce.

What I wasn’t aware of at the time was that I was reinventing myself. I was embodying the woman that I should have been all along. I had forgotten who she was and what she looked like, but she was still in there. She was a skier who hadn’t skied in many years, she was a tennis player who hadn’t picked up her racquet in too long, she was a runner who hadn’t put on running shoes in a decade. Most of all, she was a stylist who could really put an outfit together. And, as she went on her first few dates, she realized she was also funny and interesting and maybe even attractive.


woman in sunset
Dating, I came to find out, was a way for me to continue my reinvention process. I learned more and more about myself with each interaction. With each date and each passing month, I was gaining more and more confidence in myself and really homing in on my personal style. Now, when I walked into a restaurant or café to meet a date, instead of feeling like a frumpy mom I felt like a stylish and sexy single woman. If I said it was a transformation, it would be an understatement.


At the same time, I was learning what I wanted and didn’t want in my next relationship and partner. While writing and re-writing my dating profile bio, I was figuring out who I was and how I wanted to project that. While practicing selfies (yes that is a part of this new dating world) and choosing photos for my dating profile, I was deciding how I wanted to present myself and what story I wanted to tell.


You don’t have to do all this at once. This was a year-long endeavor for me. Take your time and try to enjoy the process. Most of all, be kind to yourself throughout this time. You will have times when you don’t feel like pushing yourself to wear that new top or go on that date or even get out of bed for that matter. It’s all ok and it’s all part of the journey. And it all starts in your closet!



alyssa dineen
Alyssa Dineen has been an editor, stylist, and art director in New York for over 20 years. After she divorced at age 41, she began online dating, and rediscovered herself in the process. Through this journey, she found many people out there that could improve their dating profiles and while doing so, their understanding of what they want. Founder of Style My Profile, Alyssa now helps online daters transform their destinies by taking charge of their profiles and their dating experience with her unique approach of “intentional” dating and self-discovery.
An acclaimed stylist and dating expert, Alyssa has appeared in The New York Times, Today Show, Goop, and NBC.com. You can work with her one-on-one, and she also offers workshops and a membership to be part of the Style My Profile Community. You can find out more at stylemyprofilenyc.com
Book link and photo:
Order The Art of Online Dating here
The Radically Positive Way
to Separate
Gabrielle Hartley with Elena Brower
Available on Amazon
“Potent, accessible tools for your family and your future.”
— Gwyneth Paltrow, New York Times Bestselling Author and Founder of GOOP



DISCLAIMER: The commentary, advice, and opinions from Gabrielle Hartley are for informational purposes only and not for the purpose of providing legal advice or mental health services. You should contact an attorney and/or mental health professional in your state to obtain advice with respect to any particular issue or problem.


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