Effortlessly Herself: Style, Motherhood & the Power of Dressing with Intention
How one San Francisco mom and tech marketer uses style as self-care—and a way to stay grounded in who she is.
What does it look like to juggle a fast-paced tech job, motherhood, and a deep passion for personal style—and still show up looking cool, confident, and completely yourself?
Meet Jenn: a San Francisco-based marketer, mom, and fashion enthusiast whose wardrobe is as intentional as her approach to mental wellness.
In our chat, Jenn opens up about how rediscovering her style became a powerful act of self-care post-motherhood, why great bottoms are the secret weapon in her closet, and how embracing Tibi’s styling philosophy helped her reconnect with her identity.
I first discovered Jenn on Instagram, at everydayjenn, where I’ve long admired her from afar for her chill, modern, yet often also classic style and the way she shares thoughtful insights on fashion, identity, and balance.
We even almost met during my recent trip to San Francisco—which made this conversation all the more special.
Beyond her professional and personal roles, Jenn's Instagram feed offers a window into her world, showcasing her effortlessly chic outfits, candid moments with her daughter Mara, and thoughtful reflections on balancing work, family, and self-expression. Her posts are a testament to the power of fashion as a tool for confidence and self-care, resonating with many who navigate similar life intersections.
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Let’s get to it, Jenn :)
How would you describe yourself, what you do and your style in a nutshell?
To start, thank you so much for taking the time to chat with me, Ewelina! Such an honor as I admire your style and writing. I seriously love how the internet has allowed people like us to meet (even if we’re in distant parts of the world) and connect about shared interests like style.
…I cannot agree more, Jenn :)
I’m a San Francisco native and a working mom in tech, who has a deep passion for self-growth and mental wellness. I spend a lot of time trying to be present with myself and others, reflecting so that I can continuously learn, and generally being intentional about investing my time in self-care and other priorities that fuel me.
A big part of that self-care and intentionality is investing in my own personal style, which I view as a valuable form of self-expression, confidence and overall mental wellness (people truly do feel better when they like how they look and what they wear!).
My style adjectives are chill, feminine, and edgy, and I love reflecting my casual, active lifestyle and personal interests in my personal style.
I did so much people watching when in San Francisco, back in September last year; observing how individuals spend their days.
How about your typical day? What does it look like for you in San Francisco?
I have “traditional 9-5” Monday-Friday hours, working as a marketer in tech. During the work days, I typically start my mornings taking my daughter (Mara) to school; then I head back home to start my work day. During the pandemic, I became a full-time remote employee so I have a lot more flexibility throughout the day to get work done while also doing personal things when I have downtime (running errands, working on creative projects, quick lunches with friends, etc.). When my work day ends and Mara is done with school, I spend quality time with her and my husband for dinner and bedtime. After Mara goes to sleep, I wrap up the night chatting with my husband or watching our favorite TV shows.
This sounds so relatable, Jenn.
Style-wise during the weekdays, I try to optimize for comfort since I’m at home most of the day. But I try not to compromise on the personality that comes through my looks. Like many others, when the pandemic first started and I started working remotely, I wore a lot of the same clothes (or even pajamas!) for my meetings and getting work done.
However, whenever I actually got dressed at home, I noticed a difference in how I felt putting on different clothes (other than sweats or normal house clothes). Getting dressed, even slightly, created a slight boost of confidence in how I perceived myself.
And it also was a helpful, visual transition between my home and work life.
On the weekend, I usually dress more liberally, while still being comfortable and durable enough (high chance I will get dirty from kids activities!) to take my daughter to ballet class, playdates and generally being active with the family.
Jenn, what are the key pieces that you know you rely on to create stylish yet practical outfits for your daily life?
Key pieces for me are the following, and they’re roughly in order of priority and importance to me:
A really good pair of bottoms: The part of my closet where I intentionally have invested in lots of options is my bottoms (pants, skirts, etc.). They’re the pieces that really prepare me for an active working mom lifestyle
(Does it have pockets to hold my things? Can it be easily washed? Can I run around in it?)and often act as the foundational piece for my outfit to build upon. I find that my variety in tops feels minimal compared to the different bottoms I have. As much as I want to invest more in tops, I’ve found that the balance has been okay because small tweaks to the same bottoms can vary a look a lot.
This is so interesting, Jenn! I have actually written about the good bottoms in one of my recent posts. For me, a good bottom is somewhere on the chill and modern scale. I try to stay away from classic pants or skirts. Why? More about this here:
Am I ready for spring?
I don't have many different mood boards on Pinterest, but I do have a separate one for each of the main fours season and hence also for Spring.
An easy to throw on jacket with personality: Living in San Francisco, a jacket (at least a light/medium weight one) is necessary almost all year round. Because I’m often active and on-the-go, I’ve found more oversized, throw-on pieces
with larger arm holesto be really instrumental in layering for convenience, warmth and style.A comfortable (but fun!) shoe: As I’ve gotten older, my feet and back hurt a lot easier (not just me right? 😅). So it’s critical to have comfortable shoes that also feel special. Shoes are practical but they’re also an accessory that can really change up a look. To maximize comfort,
I’ve almost completely phased heels out of my closet.
Lastly, a practical bag with a point of view: I often have a handful of things to carry, ranging from my personal items to Mara’s snacks (I swear she is always hungry), so
I need a good bag to carry them all while not looking frumpy or boring.
So, how do you make sure that your outfits reflect who you are and how you want to feel? Do you plan your outfits in advance? If so, please share your process for planning outfits to suit your busy lifestyle - from school runs to business meetings?
I don’t have a physical process or routine (like your amazing Sunday outfit planning!), but the 2 main questions that run through my head everyday are:
(1) What occasion do I need to dress for and
(2) what mood am I in or what vibe do I want to give off?
Being intentional about answering these questions everyday, I find that I end up with a variety of looks because my answer to the second question (my mood and the vibe I want to give off) is ever changing and never 100% exactly the same. My outfits may be similar some days, but I feel like there’s always something different about it (whether it’s a different accessory, shoe, etc.) to make it feel fresh or unique for the day.
Here are some looks that put my questions into practice:
Watching Mara’s Chinese New Year school performance (indoors) on a rainy day, but I still wanted to feel festive
Taking Mara to see Disney on Ice with some family friends, and I felt excited and overall cheerful
Heading to Disneyland, where I wanted to feel comfortable for a long day at the park, on theme (I’m a huge Disney fan) but stylistically still me
Checking out a local Tibi event last, where I was going to see and meet Amy Smilovic and Sheri McMullen. I wanted to feel supportive and excited about the brand (which I am!), while still having a semblance of my own style come through (ideally didn’t want to wear all Tibi).
Now over to a question that I know you were happy I asked. This is about motherhood and style.
In what ways has becoming a mother influenced your fashion preferences and shopping habits? How do you manage to maintain your personal style, Jenn, while navigating the daily responsibilities of motherhood?
Thanks so much for asking this. I love this question so much because becoming a mother has had a huge impact on my life and my personal style. Ultimately in a good way, but it was a long journey to even get to where I am today.
Prior to becoming a mother, I had always loved clothing and style, but I never felt the need to understand it as deeply as I do now. I generally knew I liked dressing in an “effortlessly cool” way (with feminine and edgy vibes). But I just generally loved style, seeing what others were wearing, and staying on top of what the latest trends were. I had more time for experimentation since I was younger with less responsibilities.
Most people know that raising a child is a big deal, but not enough is said for how it can change you, turn your life and routines upside down, and make you feel lost.
After I had my daughter, it was one of the first times in my life that I felt “lost” with my style.
That feeling was exacerbated from becoming a mother during peak pandemic (July 2020), which profoundly impacted the world. My body and proportions changed (pregnancy hair growth to postpartum hair loss, and omg, it was the first time I had “large” breasts, which felt so jarring and confusing on my petite frame), my lifestyle changed (learning to raise another human being but also living a more remote life during the pandemic), and my priorities changed.
Amy Smilovic summarizes the postpartum experience so well here (it’s a highlight on her IG called, “Pregnant CPs”):
I feel Amy’s experience so much to my core - the root cause of me feeling so lost was “never nailing who I was, stylistically speaking, BEFORE I had kids”.
When Mara was born, I had less time to get dressed and think about my style. I started conflating my entire identity with either being a mother or a full-time tech employee because of how all-consuming everything was.
If you enjoy reading about and relate to other stylish women and mothers, here are two other interviews that I did recently:
My styling needs also changed. I needed breastfeeding-friendly tops and large, practical bags to carry around bottles, diapers, extra changes of clothes, etc.
Seemingly “necessary” purchases for motherhood and my new body combined with less time for myself and pandemic lifestyle changes resulted in an outdated, ill-fitting wardrobe that felt so out of touch with who I was as an individual and as a mom. On top of that, I had a serious bout of postpartum anxiety and work burnout from trying to give everything my all with minimal regard for my own needs.
Doing regular therapy and self-improvement ultimately helped me navigate much of my anxiety, which was causing me to feel so out of touch with my own needs. As part of that journey, I redefined my priorities and started to invest more in myself again. A big part of that self-care and investment was going back to my passions and rediscovering my style.
About 3 years ago, I came out on the other side with a re-calibrated sense of self-identity that was multifaceted (not just tied to motherhood or work). I’m a loving mom, an accountable tech employee, a caring wife, a dedicated family woman, a mental health advocate, and an expressive individual with interests like style and kpop. Having that understanding of self has given me the freedom to truly lean into and expand my personal style to encompass all of those identities.
Thank you Jenn for speaking openly about your postpartum struggles and your vulnerability that is so tangible. It couldn’t have been easy for you.
I love how you re-emerged after 3 years and were able to define who you are so clearly.
I tried to illustrate my personal style evolution: from “effortlessly cool” girl pre/during pregnancy → new mom living in leggings and desperate to integrate “trends” at the time (like tie-dye) just to feel something → current day me who better balances my own personal style with my active mom lifestyle.
Now, you’ve already mentioned the brand Tibi a couple of times.
How did you discover Tibi? How has the brand influenced your approach to fashion and styling?
I tried on my first Tibi piece via Rent the Runway about 7-8 years ago, and I loved it. It had all the aspects of CMC (chill, modern, classic) that they pride themselves on, and I distinctly remembered that top because of how special it was. Because their price point was a bit high for my budget back then, I didn’t really follow along with the brand actively until the pandemic (like many others!) when a friend turned me onto Amy’s IG page.
Amy’s styling philosophies along with Tibi’s aesthetic helped articulate so much of what I subconsciously gravitated towards in my style. Her concepts helped diagnose what felt right or wrong about a look. Having that clear language and nomenclature to talk about style helped me gain so much more clarity with my own personal style. It also increased my accuracy in properly and consistently conveying my personal style through my looks.
The most revolutionary Tibi concepts that helped me be smarter and more creative with my closet were (1) avoiding a bifurcated closet, for example - casual vs dressy clothes and (2) thinking about my clothing as “tools” to wear differently and create different looks. Investing in valuable-to-me Tibi items and having these two particular concepts have expanded the possibilities of my wardrobe in countless ways.
I now rarely have the feeling of “I have nothing to wear”, whereas that feeling used to crop up more frequently. Finally, I love the brand’s ongoing discussions about style (via Style Classes, Instagram, etc.) with the Tibi-interested community. Their thoughtful (as much as a brand can be) approach on bringing it back to you, your preferences and lifestyle continues to help people understand their own styles in more profound ways.
Examples of using my clothing (like this Tibi strapless top and Ganni leopard dress) as “tools” to wear in different ways and create distinct looks:
Finally to a subject that is wholeheartedly dear to me, i.e. sustainability.
So dear that I’ve interviewed here also women like Missmatch or Tiia, whose whole closets are filled with vintage and preloved items:
So, how important is sustainability in your fashion choices, and how do you incorporate them into your wardrobe?
Naturally, high-quality clothing (often associated with premium brands) or buying second hand are important factors when I think about sustainability. However, the concept I tend to gravitate towards the most (regardless of brand or designer) is getting good cost-per-wear from my clothing and generally making sure I can style and wear my clothes A LOT.
I think deeply about the clothing I get (whether it’s new or secondhand) to make sure I’m being eco-friendly and not cycling through clothing season after season. A core habit I’ve built up is to style something in numerous ways before I decide to keep something. If I can’t think of countless ways to style something, I will likely return it unless I have another strong reason to keep it.
As much as I love buying premium or sustainable brands, my mentality is that getting the occasional item from Zara or Target is okay too if I’ll wear it a lot.
Zara cream top I’ve worn so many times:
Styling a Tibi cardigan numerous ways before keeping it:
Wearing my American Eagle red pants in numerous ways:
It has been so good to chat with you, Jenn :) And as we are about to round our conversation up, here’s one more question that I ask all of the other stylish women, I’ve been talking to.
The question is: What are your future goals for your personal style? Are there any new directions you’re excited to explore?
Overall, I’m pretty happy with the trajectory that I’m on in continuing to hone and express my personal style; my main focus recently has been tackling gaps in my tops and jewelry to give me more creative range.
To keep myself accountable, I use Instagram as my regular way to share my creativity, style and lessons, so I’m sure you’ll continue to see my progress and evolution there (dare I venture back onto TikTok too?).
To further my continued growth in style, I am also inspired by people like you to explore writing on Substack (in addition to the mental health one I occasionally write in) or eventually get back into styling for others since I used to be a remote stylist!
My relationship with style is always evolving, and I’m always excited to explore and learn more when it comes to personal style.
Because clothes don’t need to be just clothes. They are often used for creativity and self-expression, they can be the bit of self-care you need on a shitty day, they can be the armor you need to tackle a tough situation.
Some people really underestimate the power that feeling good and confident in what you wear can bring, and I love developing my personal style and sharing that joy and understanding in whatever way I can.
I can definitely undersign this with both of my hands, Jenn. This has been such a pleasure to get to know you, understand how your approach style and the role clothes play in your busy professional and family life.
Thank you, Jenn.
With love,
Ewelina