How to Practically Evolve Your Mom Style

A few experiments to help you find your (new) authentic outward self

Mar 25, 2025

Let’s talk about getting dressed.

When I was a few weeks postpartum with my first baby the realization hit me like a ton of bricks: I had nothing to wear. I was lucky enough to have a happy healthy baby and I was eager to emerge from my winter pregnancy cocoon and make a few mom friends. But I certainly didn’t feel like a butterfly. Rather, I was an uncomfortable stranger in someone else’s fleshy and weakened body, far from the confident and stylish dresser I had considered myself pre-baby.

In truth, my style and wardrobe had been on hiatus for longer than just the nine months preceding our son’s birth. The two years leading up to baby boy were physically and emotionally traumatic, filled with injury, sadness, fear, and a few cross-country moves. Life’s unrelenting twists had held me back from any big shopping sprees.

After having my son, I felt a raw hunger to reemerge into the world as an outwardly beautiful women. While my husband urged me to spend some serious cash on myself, I didn’t feel ready to commit to a closet overhaul.

I didn’t know how I wanted to present to the world. I didn’t have a style.

Matrescence hits everyone differently, and it certainly harbors more existential change than just the impulse to change our clothes. At the same time, wanting to evolve our style as moms does feel almost universal.

When you consider the root of matrescence is a drastic hormone change akin to adolescent hormone revolution we must each endure, the desire to change and resolidify our outward style as moms makes more sense. I don’t know about you, but my own adolescent nose was stuck in between the pages of Teen Vogue taking style quizzes and ripping out my favorite fashion spreads to plaster onto my bedroom walls. I would take the phone cable out of the wall and plug it into my 10-lb laptop to dial-up the internet, where I’d scour retail websites, like Abercrombie.com, copying and pasting the images of outfits I liked into Word documents. These were my homespun Pinterest boards, made before the platform existed.

I carry this same gusto with me now as I attempt to redefine my style to establish authentic self in motherhood. In the two sections of this post to follow, I’ll share a few tools I am using to evolve my style and feel good in what I wear. My hope is that my own approach might spark some ideas for each of you!

And before I dive in, I have to admit I had a ton of fun working with Chat GPT to do this work, so I hope you can also get some enjoyment out of the process.

Use AI to Assess Patterns and Identify Your Core Authentic Style

Step 1: Go Deep Into Your Pinterest Archives

I recently had the idea to look back at my aptly named “clothing” board on Pinterest to see if I could find some connective style tissue spanning my history on the site. My “clothing” board feels like a cringey altar, built to worship the latest fashion trends without much editorial perspective. But, as a visual reference to the looks I’ve idolized in the last 15+ years (since high school), its the closest thing I have to my visual style DNA. I choose to believe it contains some nuggets of insight about my authentic core self, not just what the fashion industry wants me to like.

I took to chat GPT to help me parse through the pile of pictures. I started by screenshotting chronological sections from the board and inserting them into a PowerPoint, simply labeling them with the approximate timespan they were from.

I fear I must show at least a few receipts...

Step 2: Upload your image guide into GenAI

After saving my pretty basic PPT with screenshots from Pinterest aligned to the approximate years I pinned them, I uploaded the image guide as a PDF into ChatGPT along with this pretty detailed prompt:

Style Evolution Analysis Prompt
I am uploading a PDF with screenshots of my Pinterest "clothing" board over time. Each page includes images I pinned during a specific time period, with the approximate date noted.
I want an analysis of my evolving style to help me build a timeless wardrobe that reflects my true aesthetic, rather than following momentary trends. While some older pins (especially from the 2000s and 2010s) now feel cringeworthy, due to their trendiness (e.g., neon, Aztec prints), I’d like to understand what underlying elements still resonate with me.
Please analyze and classify my style evolution in the following ways:
1️⃣ Core characteristics I’ve consistently been drawn to over time
2️⃣ Style types or aesthetics that emerge from my choices
3️⃣ Other common themes or visual patterns across my pins (e.g., settings, moods, or styling details)
Additionally, consider broader fashion trends from each era to help separate what was trendy at the time from what reflects my personal taste.

Step 3: Iterate with the Chat

It’s always a good idea to refine GPT output to truly meet your needs. In my case, I wanted to start with a greater amount of AI analysis, so I could read and process the GPT’s broad narrative, then narrow down to a few usable insights. Upon first review, I was impressed with the GPT’s ability to scan and assess hundreds of images as well as it did. Without sharing the full back and forth chat, I’ll share where we landed:

Your Personal Style Thesis
✨ Effortless, Timeless, and a Little Whimsical ✨
1️⃣ Relaxed but Polished – Soft, drapey silhouettes that feel put-together without being stiff.
2️⃣ Textural & Cozy – Knitwear, natural fabrics, and layering for depth and interest.
3️⃣ Slightly Artsy, Never Overdone – Unique details (like statement earrings, subtle patterns, or vintage-inspired elements) add personality.
4️⃣ Bright, Cool-Toned, and High-Contrast – Colors that make you glow: jewel tones, crisp whites, cool greys, and rich blues. No taupe, beige, or muted pastels.
5️⃣ Quality Over Quantity – Well-made, timeless pieces that last. No fast fashion or flimsy fabrics.
6️⃣ Comfort First, Always – Nothing fussy or restrictive. Clothes should move with you.
7️⃣ A European Touch – Classic, effortless styling with a slightly French or Scandinavian influence.
8️⃣ Understated Confidence – Strong outfits built from great basics, not loud trends.

Step 4: Have Fun With It

The world is your oyster when it comes to leveraging GenAI for creative thinking exercises like this one. In my own case, I did a few additional analyses:

Color Season Analysis: Every time a new color season filter pops onto my TikTok For You page, I try it out, only to get more confused about my own season. I’ve dabbled with asking ChatGPT to help me with color season analysis before, but figured I’d make another attempt here, with some more coaching. I told the GPT about my skin undertones, hair and eye colors, and a few colors that I always get compliments on wearing. We went back and forth a bit and landed on me being a bright winter. I now have a list of hex codes with some of my (likely) best colors.
AI Rendering: This was truly just for fun, but I gave the GPT a basic description of my physical form and asked it to follow the style thesis we had worked on together and render some images “of me” dressed that way. I think these outputs are pretty generic, but were fun to build.
Seems like I'm going to be investing in some brown sweaters...
Buying Guides: I had the GPT help me build a guide of several questions or “checks and balances” to help determine whether an item needs to live in my closet, or just visit temporarily. Perhaps, most helpful from the list, was a core 3-word description we landed on for describing my style: soft, relaxed, and a bit artsy.
Here is a list it created for me of several retailers that match my vibe. I knew we were onto something when a few of my current favorites (like Veja) were on the list. I’ll have fun exploring some of these other brands, although I’m committed to buying as little as possible new.
Everyday Wear & Elevated Basics
1. 🧥 Sezane – Effortlessly chic with French-inspired knits, soft tailoring, and unique textures.
  👖 Everlane – Minimalist, high-quality basics in great fabrics (especially their cashmere and denim).
  👕 Quince – Affordable, luxurious staples like silk blouses, cashmere sweaters, and structured tees.
  🩳 Eileen Fisher – Soft, drapey silhouettes in high-quality natural fabrics.
  🌿 Jenni Kayne – Luxe, California-cool knitwear and effortless everyday pieces.
2. Artsy & Whimsical Touches
  🎨 Paloma Wool – Artsy, unique prints and textures with a laid-back feel.
  🧶 Babaa – Beautiful, chunky knitwear made in Spain with ethical production.
  👜 Cuyana – Minimal but interesting accessories (gorgeous leather bags, soft scarves).
  👚 Doen – Flowy, feminine pieces with a vintage touch—great for soft, romantic vibes.
3. Shoes & Accessories (Comfort Meets Personality!)
  👢 Aeyde – Minimalist but special shoes with a European feel.
  👟 Veja – Stylish, comfortable sneakers that feel effortless but cool.
  👜 Mejuri – Delicate, high-quality gold jewelry (perfect for your statement earrings).
  🌟 Wolf Circus – Playful, artsy, and sophisticated jewelry.

Invite Play Into Your Wardrobe With Clothing Rental

What started with the quiet hope to bridge my body for a few months between birth and “bounce back” has extended almost two years to the present day. Now, almost six-months postpartum for a second time, I don’t see myself stopping my monthly clothing rental subscription anytime soon and will recommend the service to anyone who asks. I utilize Nuuly as the site with the most inventory that I would actually wear across a range of occasions and body sizes. It’s $100 a month and has now shepherded me through two postpartum phases and a full pregnancy. « I swear to all that’s holy, this is not an ad!»

Here are some use cases I see as best fit for clothing rental:

Working from home, I don’t have a 5-day-per-week need for nice pants, but rather an occasional need for a cute top. Statement earrings do the trick most days, and on the ones where I need a little something extra, I get to select from six new-to-me options.
My rental items (usually) fit my body at its current size, which is ever-changing as a pregnant, then postpartum, and now nursing person. We all know that number-based sizing is wildly inconsistent, so I love that I can search through fit reviews by weight and height and get a decent sense for what will fit me before it arrives at my door. No try-on necessary.
I relish in the little rush I get when planning for the month ahead, daydreaming about near future events, celebrations, and the changing seasons.
Renting feels more sustainable than buying expensive trendy clothing pieces that will sit unworn in my closet. When I really like a rental piece, I have the opportunity to buy it at a fractional cost, that’s calculated based on how much the piece has been worn.
We need to luxuriate in moments of self-care as moms. Seeing my clothing rental bag on my doorstep at the outset of each month gives me a major dopamine hit.
I more often will choose a “loud” or playful pattern, a new cut of pants (see barrel leg jeans), or a statement piece to rent, rather than buy. Playful experimentation is what helps us evolve our style.

Did I miss anything? What tools and resources have you utilized to evolve your own aesthetic as a mom? How do you get inspired by your current closet?

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