I always talk about dressing the life you actually live and not some version of it. So when my friend told me about it, I knew I wanted to share it with you.
This was written by my friend Sharon. We’re close in age, but we live in different places with different bodies, different lives, and different personal style preferences. He originally wrote it to get another book, but when that happened, I thought: this is the kind of honest, relatable experience you might enjoy. Sharon is a grown woman who is rediscovering who she is through her closet and I thank her for sharing her story with us.
– Alison
When Your Wardrobe Stops Feeling Like You
It started one of those mornings – standing in front of a closet full of clothes with nothing to wear. I was in the middle of life and in full fashion. Where was the stylish girl who was voted “best dressed” in 8th grade and “most dressed” in 12th (titles I find incredibly optimistic, considering I’ve been living in the same black jeans for years).
Every attempt to get dressed felt like an identity crisis. Somewhere between menopause, working from home, and bringing my oldest son to college, my style had disappeared. It can be very difficult to feel like yourself again after becoming a parent. And when my youngest turned 17, I realized—yikes—it was alongtime since I felt like myself.
So, I asked for help: a personal stylist and wardrobe organizer. I figured it would at least help me get rid of the things I was saving for some future fantasy event and maybe get me out of my style rut. What I didn’t expect was how much this process would change my relationship with clothing itself. I began to see my wardrobe as a functional support for my busy life—a tool that could make dressing less overwhelming and help me feel like myself again.
What Closet Editing Really Looks Like
The artist I worked with,Terin Trudeaucame by personal referral from a friend on Instagram. Terin is a stylish mom of three who started helping other mom friends organize clothes and organize their closets and it turned into a real business. She just wants to help other moms feel good about themselves and that sounds like a good fit for me. And his prices were reasonable compared to other stylists I interviewed.
When he arrived, he didn’t start by judging my wardrobe. He asked about my health. What do I do most days? Where am I going? What do I do?actuallydo you want to dress up? It wasn’t about styles, it was about my lifestyle.
Then came the cleaning. She set up a rack to help us organize, and we went through all the things in my closet. If it didn’t fit my current body or lifestyle, it went. For some pieces, giving up was easy. For anything we weren’t sure about, I tried it and thought about it honestly. When we found something really similar (apparently, there was something like a lot of black t-shirts) we decided which one we wanted to keep and said goodbye to the others.
We also made a small section of things that I didn’t know how to work into a dress. We would come back to these later.
Her top cleaning tips are incredibly simple:
- Use small matching hangers to create visual calm
- You don’t need to buy new parts just to make something “work”
- If you’re on the fence about something, give it two months – then wear it or leave it
When he left, I had seven bags to donate. And I hadn’t gone through my shoes and accessories.
Rediscovering Your Personal Style (Not Someone Else’s)
I was secretly hoping that he would just tell me what to wear. Instead, he helped me see what it wasIit actually pulled forward now, which was very helpful.
She showed me how to recreate the easy, flowy vibe of my favorite kaftan style dresses using flowy pants and tops. She helped me move beyond skinny jeans and showed me how to wear modern styles that look good on me.
He did not impose his own ideas of style. He would ask why I didn’t like something, see if we could fix it differently, and always let me come to my own conclusion. We circled back to the “maybe” pile and mixed and matched to see what made sense for my revised wardrobe. We touched on trends that I might want to try and put together outfits for a few upcoming events.
LIST TIP:
Terin’s best advice was to take pictures of clothes you like. In the morning when you’re tired or second-guessing everything, scroll back to that album and copy yourself. We photographed all the clothes we worked on together, and I always go back to them.
How to Intentionally Fill Wardrobe Gaps
I nervously thought that the shops would follow. Instead, she asked me to shop my closet first, mixing and matching pieces I already had into combinations I’d never tried. He then gave me a short list, aimed at my real pain points and places I like to shop:
Immediate priority:
- A quality white t-shirt with a low neckline
- Black leather belt (brown leather to follow)
- Ballet flats are easy to pull together
- Mules – a non-Birkenstock slip-on option for every occasion (I love Birkenstock, but there’s a time and place)
- New denim silhouettes: straight leg, barrel leg, and wide leg in several washes to be discovered gradually, not all at once.
- Drawstring pants for that easy, flowy vibe
- Linen buttons that can transition into the cooler months
- Tank tops with built-in bras for layering
Long term wish list:
- Army green pants – a great alternative to all black, pair well with leopard print and denim
- A black card cutout and a brightly colored jersey
- A classic black heeled sandal for work events – a comfortable item that instantly elevates an outfit
It’s true: you don’t need extra clothes. You need aon the rightclothes.
What I Can Tell Anyone About Personal Style
Suddenly, my closet had very few options but I had a lot of clothes. Getting dressed felt easy. I felt lighter, more confident, like myself.
I wasn’t turned to the nines or straight off the page of a magazine. But I was completely me – free, put together, with little personality to show.
Practical takeaways:
- When in doubt, add a belt.The change is truly shocking.
- Try different necklines.Showing more skin (nothing offensive—I’m a modest dresser) can help balance it out and make it look “okay.”
- We style the details.Tuck things in, roll up the sleeves, open the collar. Small tweaks add a lot of interest.
- Finish with jewelry.A basic jeans-and-t-shirt look can be stylish with a nice necklace stack and some bracelets. Jewelry makes clothes feel purposeful.
- Take pictures of the clothes.You will absolutely thank yourself for the quick mornings.
- Your style is not gone. It just requires a little planning.
Working with a stylist wasn’t about being fashionable—it was about making life easier. And honestly? Getting it for myself and it was worth the money. If you can’t find a reasonably priced stylist and planner in your area, keep your eye out for a trendy mom you know. Another set of eyes is always helpful!
Frequently Asked Questions About Working With A Personal Stylist
