I Overthink Every Outfit, So You Don't Have To | 09
Embracing Freedom and Fashion: Parenting Lessons, Kids' Personal Style, Letting Go of Control, and My Outfits of the Week
"The biggest lesson I’ve learned as a parent is that kids don’t need you until they need you... and then they need you to make dinner, find their phone, and be their personal Uber driver." – Jim Gaffigan
Freedom, Fashion, and Letting Go
Last week I decided to give my daughter the freedom to dress herself. If you know my girl—or know of her—you know that she is the ultimate independent and free-spirited child. She beats to her own drum and very firmly knows what she likes and what she does not like. I have never seen a 7-year-old have boundaries the way she does. I have also never seen a 7-year-old feel so sure in who she is.
Listen, she still gets nervous or worries—all that normal young child stuff.
I’m usually pretty good at letting her have the freedom to do what makes her feel comfortable. But for some reason, I have a really hard time when it comes to how she dresses. I started thinking about how hypocritical that is of me. I sit here every week and encourage our team to wear what makes you happy, wear what makes you feel good—yet I put boundaries on my daughter’s creativity.
So she got dressed and asked me if she could keep the outfit on. I hesitated, but eventually asked her the following: “Does what you’re wearing make you feel good?” She said, “Yes.” Then I took a deep breath, probably twitched a few times, and said, “Then without a doubt, that’s what you wear.”
Now listen—I’m not sending her out in public looking unwell, so we have to have some level of boundaries here. But it was a really good first step. My response to her when she asks this is usually to make a face (like yikes), or say, “Let’s go upstairs and pick something different out,” which then leads to her protesting.
She strutted around the dining room table in her new look. I told her, “You are so fashionable… you should have the fashion blog!” She turned to me and goes, “Mom, I don’t need a fashion blog.” I was suspicious of this answer, so I inquired further. She said, “I just wear what I like.”
No overthinking. No comparison. No desire to be influenced to wear anything that isn’t what she likes.
I wish I could bottle that self-confidence up and kindle it within her forever. I have an inkling there will be a time when that bold confidence dissipates. But what I always love about being a mom is the lessons I learn from my children.
My son is ten and is coming into the age where he’s actually developing his own personal style. He’s attempting to grow a broccoli haircut (it makes me sick), and he’s made it clear that he really loves to wear Vineyard Vines. For Christmas, I bought him a How the Grinch Stole Christmas sweatshirt for “Ugly Sweater Day” at school. This is one of those themed days that make up the entire month of December and stress parents out all across the continental United States.
PSA TO SCHOOLS ACROSS AMERICA: We do not want to have to remember to dress our kids up every single day for 14 days before Christmas—it is the most stressful yet amazing time of the year. Thank you. Sincerely, Parents Everywhere.
Needless to say, he was mortified. He didn’t know how to tell me that, in his mind, it was horrible and he would absolutely never wear it (and to this day, never has). Eventually, he told me. And I still, to this day, try to tease him into wearing it.
So many moments in parenting really take you aback. Like the moment your child takes their first steps, says their first words, throws a ball, or goes off to school. These are small moments we want to bottle up and hold on to forever. I just wasn’t ready for my kids developing their own personal style to impact me in the same way.
It just hit me that they are their own people. And for the past ten or so years, I’ve been able to dress them, guide them, and coach them in so many aspects of life. And now we’re entering the phase where they want autonomy, freedom, and ownership of their own lives.
I thought sending them on a bus to school was the parenting moment that hit me the deepest—but I’m actually realizing this one is giving me way more feels.
I’m sad that they’re not my tiny babies anymore, but I’m proud of who they are. I’m sad that they need me less, but I’m proud of their ability to advocate and identify what they want. I’m sad that they won’t let me dress them, but I’m so, so proud that they know what makes them feel “good.”
Sunday
Sport Mom Sunday. It was absolutely frigid by me, so I was bundled up for the Tundra of late April. I wasn’t planning to photograph this look—but I had to make sure the world knows about Dudley Stephens fleeces. These are the warmest, most stylish 'sweatshirt made of fleece' I own—and I love them for the winter months. I know we’re headed into summer (finally!), but keep an eye out in case they go on sale. You’ll be so glad to have them once the cold rolls back around.
I also bought this hat after learning that the owner, Tom Davis, is the trainer behind The Famous Miss Peaches. So naturally, I had to support. Also, I love dogs... a lot.
Monday
This skirt was a bit of a spring splurge, but honestly—it delivered. I paired it with a white tee, my favorite Target sandals, and the bamboo-strap bag you all love as much as I do!
Tuesday
Never have I EVER gotten this many compliments on a dress—like, in all 37 years of existence. Gen Z, Boomers, random strangers—everyone was on the same page: this one’s a winner. I kept it classic with ballet flats and a pearl drop earring. Simple, timeless, and apparently… crowd-approved.
Wednesday
A solid blue linen dress kind of day. It felt a little plain on its own, so I styled it with a chunky charm necklace and this navy striped lady jacket. Added my favorite gold shell earrings from Amazon. And—shocker!—my favorite Target sandals make another appearance, this time in white.
Thursday
Loving the nautical vibes this spring. This striped “sailor” sweater was a total steal from J.Crew last year (insane clearance find!). I paired it with the most adorable gold starfish earrings and classic white denim.
Friday
The Anthropologie Somerset Dress is like an electric drill. Yes, you read that correctly.
I’ve never used an electric drill, so I can’t speak from personal experience. In fact, I’m fairly certain my husband wouldn’t let me within a 20-mile radius of one because I’d probably drop it on my foot or somehow drill into my own eye. But from what I’ve gathered in my extensive (i.e., five-minute) research, the electric drill is one of the most versatile tools out there. You can create holes, secure screws, and fasten just about anything—from plywood to metal.
Somewhere, dads across America are shaking their heads in frustration, wondering how I managed to survive this long with such a tragic lack of tool knowledge.
But back to the point: the Somerset dress is the electric drill of dresses. It comes in a million patterns, shades, and colors. You can wear it to work, to a BBQ, to a Communion, to a graduation party… the possibilities are truly endless.
I’ve had mine for about four years, and I still always reach for it. It’s the dress that never lets me down, unlike my odds of successfully operating power tools.
Saturday
I usually skip Saturdays because, well, I’m tired of getting dressed. But these shorts are AMAZING, and I’m a recovering gatekeeper. They’re long, super soft, and oddly trendy. The price is so affordable—I have them in navy blue and red. I plan on wearing these all summer.
Which of these looks did you like best? Have your kids started developing their own personal style—or expressing independence in other ways? How are we feeling?
Ain’t no hood like Motherhood.
Thank you for being here and taking the time to read my work. I appreciate you all beyond words.
Love you guys! xo,
❤️ Liked this post? Tap that heart so the algorithm knows someone’s out there.
📩 Think a friend would love this? Share it—good taste isn’t meant to be gatekept.
📸 Want more style and unfiltered ramblings? Follow me on Instagram @timelesslytraci. Tag me if you post—I’ll be in the comments with emojis, enthusiasm, and yas queens.
If you enjoy my work and want to support the content I create, consider BUYING ME A COFFEE ☕🍵—think of it as a virtual tip jar to keep the ideas flowing!
Some of the links in this post are affiliate links, meaning I may earn a small commission if you make a purchase through them. This comes at no extra cost to you, and it helps support my content and allows me to continue sharing the things I love. Thank you for your support.
Love the Sommerset dress and the sailor sweater is fabulous....the bamboo bag is great. 😃 I get giving them independence, went through it with the boys. The first time they wanted crew cuts, it's just hair, the first shaved up sides ponytail on top, it's just hair (D not G) that was my montra...now they are all pretty buzzed...
Cute cute cute! Especially that white gap dress old and the navy red shorts 👀.
Gotta say, at 37 my biggest goal in life is to have the confidence of your 7yo daughter.
ALSO! I regularly get mad at my 7yo boy for never wanting to wear ANYTHING I buy for him. He only wants to wear soccer jerseys. Which are cute too but I get him really cute stuff!! But he is funny about sensory stuff, which makes him very particular about comfort and clothing. Which I TOTALLY get because same. So why does it still irk me so much?