The secret to an effortless outfit (and midlife)
From closet confusion to empty nest clarity
In 2018, I hired a stylist to come to my house and help me figure out what to wear. It was a birthday splurge, and I was certain it would solve all my “it’s time to get dressed” overwhelm.
Shira and I went through my closet, made piles, and reworked pieces into wearable outfits.
I loved the process. It felt so good to clear out impulse buys that never quite fit and the trendy, fast-fashion purchases that never saw the light of day. For the record, I’m very, VERY good at getting rid of stuff—but I’m horrible at replacing it.
And that’s part of why the style session didn’t really work for me. I was left with holes in my wardrobe and no real motivation to fill them.
Over the years, I’ve gotten better at intentional shopping and aiming for quality pieces that wear well and stand up to passing trends. But I still struggle to pull together a comfortable outfit. I want my clothes (and my life?) to give off “effortlessly chic,” and so far I’m not quite hitting either mark.
Until now. Or at least, I’m closer than I was.
A few years ago, I found Jen Andrews, a stylist on TikTok. I clicked with both her energy and her outlook on clothing. She gives practical advice that actually sticks—like her 3-color rule, and the gem: “when in doubt, monochrome it out.” So when she launched mini style sessions, I jumped—and it turned out to be exactly the motivation I needed to take charge of my closet.
Aside from expert advice and a personalized pin board with links to my missing pieces, Jen gave me homework that changed how I see my wardrobe—and got me thinking about how our attention matters.
My inability to “throw together” an outfit wasn’t because I had nothing to wear, but because I hadn’t given my clothes enough thought or attention.
I assumed that if I had the pieces, the outfits would materialize. But as anyone who’s ever thrown a dinner party or made a donut from scratch will tell you: having the ingredients isn’t enough.
We have to plan. Think things through. Be mindful of the outcome we want and work to create it.
If I want to feel confident and comfortable, it’s not enough to pop some tags and stuff my dresser drawers. I need inspiration, organization, and intentional purchases.
After working with Jen, I knew I had to finish the project—or risk ending up right back where I started: staring at a closet full of clothes and sighing (crying?), “nothing to wear.”
So I got clear on a couple of outfit formulas, edited down my wardrobe, and made a list of what to replace or buy. And in that process, something clicked:
It wasn’t really about clothes at all.
The real issue was attention. My closet looked confusing for the same reason midlife can feel confusing—because I hadn’t slowed down long enough to actually think about what I wanted.
I see this same lack of attention show up in midlife for nearly every mom I talk to. We have general ideas of how we want to spend our time, but no solid plans.
I’m not saying we need to make spreadsheets and start ticking boxes, but we do need to be more deliberate about our time and calendars—especially once your youngest hits middle school.
Middle school is the signal: they’re getting older, pulling away, figuring out who they are outside the family. And that makes it the ideal time for moms to shift focus back to themselves.
This is a major shift for us — so much so that I’ve built an entire business around it.
But you don’t have to do anything elaborate. You don’t even have to leave the couch. Just think. Journal, if you’re feeling fancy.
This simple act of thinking about what you want and desire in this stage of life (what I call the “On-Call Mom” years) is enough to start.
Daydream about what you’ve missed, or what you’ve been putting off. It doesn’t have to be big. It could be daily meditation or a yearly meetup with your college best friend.
The point is: think about it so you can start moving toward it. Honestly, you could even create a Pinterest board for your future, just like you would for style. And if you need extra support, consider me your midlife stylist.
✨ This Thursday, Aug. 21st, I’ve got another FREE workshop to help you get started. It’ll be short and to the point—and available for rewatch if you can’t make it live.
Exploring Passions & Purpose Beyond Motherhood
Thursday, August 21st
9:30–10 AM PST
We’ll go beyond hobbies and explore passions that can spark purpose. Just like putting together an effortless outfit, it’ll take exploring, experimenting, and introspection.
With so much love!
🥰 Jennifer
P.S. Jen is still has a few more openings for these mini style sessions. Check here out on TikTok and Instagram.