From millennial beige to...✨art teacher aesthetic✨Evolving style in my late thirties + 9 fun things that are bringing immense joy to my wardrobe

Is this just me?!?!

All hail Ms. Frizzle–Millennial style icon!!

I am GIGGLING to myself writing this post as we speak–while wearing my new leopard pants–because secretly, I’ve been feeling a pull to shift my personal style for a while now.

I have gone from “classic capsule wardrobe lover” to full on COLOR/PATTERN/FUNKY SILHOUETTE/MAN-REPELLER-ESQUE which I can only describe this as “art teacher aesthetic” 😂 (or, if you prefer, the science teacher icon, Ms. Frizzle, bc hooray for women in STEM!)

I didn’t really realize this could be a collective thing so many of us were experiencing–until, of course, I posted about it on stories, and was DELIGHTED with the dm’s that started rolling in!

Turns out, according to my super scientific instagram poll–70% (SEVENTY!) of you are feeling pulled toward more joyful, fun, expressive personal style!

Turns out, this is a collective experience! (Girlhood 🙌🏼)

I think this shift subtly started around a year ago, when I was officially ready for the next chapter of our lives–ready to move on from the city, starting over in a totally new house in a totally new neighborhood–it just felt like I was being pulled toward a “shake up” in so many parts of life.

But I never really stopped to *think* about this and how it relates to my personal style until recently.

To be honest, I’ve never cared much for trends, but I really could care less about what’s “cool” or not these days. I just want to put on something JOYFUL!

As one reader in my DMs put it–I think it’s a perk that comes with your late thirties–all the fucks you had to give are LONG gone now! 😆

I have long considered it part of my “job” to be constantly posting about clothes and clothing brands (and honestly, it is). Personal style has always been an area of interest for me, but somewhere along the way, I feel like I stopped doing it for “me” and started doing it for “work.”

I woke up one day, and realized it had started to feel forced, and I wasn’t even sure when that happened.

As you may or may not have noticed (you probably didn’t–because other people rarely actually realize or care about the things WE think they do?) I, for the most part, really pulled back on posting clothes for a while. Not super intentionally, but because it just felt like a chore. It didn’t feel authentic in those moments.

I think we all get caught in this cycle of continuing to do the things we’ve always done, basically on auto-pilot, because that’s just how we’ve always done it, and… we think that’s how we should continue?

Which applies to basically everything in life, right? From your daily routine, to your job, the people you surround yourself with, how you parent your kids, how you move through the world in general–and turns out, it also applies to your personal style. Who knew?

I noticed lately, I would open my closet and be like, “Welp. There’s not a damn thing in here I’m excited to put on right now. So much of this stuff doesn’t feel like…ME anymore!?”

(Also, side note, it’s just dawning on me that this “style rut” occurred at the same exact time as my “career rut”– how utterly UN-SHOCKING! 🤯 The pull for more authenticity and growth elsewhere in my life also seeped over into my personal style.)

I was just dressing myself on autopilot, not bothering to check in and ask, “is this particular style still authentic to me TODAY?”

Once I finally made that connection, it felt really good!

I’ve started being more intentional about my personal style again–and found myself gravitating to TOTALLY different things than before.

Because we’re allowed to change our minds and make totally different choices. We’re allowed to surprise ourselves! 🙌🏼

Anyway, here are the things in my current (very casual) wardrobe that ARE currently bringing me lots of joy.

Regardless of whether you’ve been feeling a shift in your own personal style, I hope you’ll love these too!

CRAZY PANTS!!!

OK I have found myself incredibly drawn to RIDICULOUS PANTS!?

Like, this is almost 37 I guess!?

After hearing

Caroline Moss

rave about *these pants from Gap* (sizing: go with your smaller size if you’re in between! I took XS) and stewing over them for a couple of weeks, I decided, I’m going to order these kookie leopard pants, dammit, and I think they’re going to be great!”

Turns out, THEY ARE. (Don’t worry, they also come in lots of normal colors!)

They are SO COMFY. The shape is oddly costume-like, but I can’t deny that for some reason, I adore them. They are so fun and expressive–they are giving Frankie/Ms. Frizzle/IDK but I’m into it.

After I posted them, many of you said you adore them too! So these are also auntie approved MANY times over.

Dare I say that after almost two decades of wearing feminine silhouettes and lots of neutrals (even though I loved it, and I still DO love these classic pieces) wearing crazy pants feels like…a vacation I didn’t know I needed? A small act of rebellion?

And *by god I wouldn't be millennial if* I didn’t remind you that *leopard is a neutral* right?

I also got wild and ordered these similar GAP pants in tomato red. (Pictured below!) Again, they do come in normal colors too, if you prefer a more minor act of rebellion. 😂 SO SOFT and so comfortable.

(Perhaps these funny shaped jeans are a subconscious FU maybe after wearing skinny jeans for so long!??!)

New obsession gap pants (SO COMFY!) in hot red. Don’t worry they have more normal colors. Go with your smaller size if in between! 😂 Madewell western belt, old flats, similar sweater

Cool statement belts:

Ok ok I’ll admit I’ve always had a thing for belts. Remember when everyone wore GIANT belts in college? I don’t think I was seen once in public without a belt for the entirety of 2007. I’ve loved statement belts at every phase of my life, and I love them still now. Turns out they go great with your classic jeans and also with crazy pants.

Here are some favorites:

Studded western belt: (Pictured above with my new red crazy pants!!) I love the subtle western vibe and slight edge this belt adds to your outfit while still feeling attainable to style!

Sculptural belt: Same here! I have the pretty light blue color and it adds a really pretty pop of color and interest while also being pretty easy to pair with a lot of items in your wardrobe.

Sezane Artemis belt: No surprise here, you know I’ve worn this for years. I own this belt in several colors and it never disappoints.

Overalls:

I got these Free People Ziggy overalls (tip: size down. The XS is plenty roomy on me) over a year ago (I also have them in the shorts version) and they have been one of my favorite things to wear year-round. They may have been the start of my art teacher style shift and continue to bring me lots of joy. (They are also SO COMFY.)

They make me feel like a cute cool mom in a Nancy Meyers movie (I’m just missing an armful of hydrangeas) when I wear them with a crisp white button down to the farmers market.

I feel like a funky chic art teacher when I style them with my Swedish clogs and a colorful sweater.

And they’re also super practical to throw on just with a longline crop bra (love these from Amazon) and a baseball cap for gardening, cleaning, and getting stuff done around the house!

Other cute styles: The shorties version of the Ziggy overalls, and also these from Anthro that are less “farmer” overall-ish and a little more minimalistic!

Sizing: These run big, I would size down!

Clare V. Purses:

It’s no secret that I am a die-hard for Clare V. purses. They come in so many fun styles, they all have interchangeable straps (they are always coming out with fun new straps you can mix and match to totally change the look of your bag!)

Their quality is great, and the customer service is even better. Also, a small, woman-owned brand–they also make a lot of their items in LA!

I used to think a classic, neutral purse was the way to go because it would “go with everything” but I’ve changed my tune over the past couple of years and found that an everyday bag with a little more personality is an even better choice–because no matter what you style it with, it makes your outfit look cooler!

There are a couple schools of thought here–choose a bag with a fun shape/texture but in a neutral color (so it goes with everything) OR choose a color that is a little more different, yet, still fits together with your everyday wardrobe–but in a mismatch-y type of way.

Clare V makes bags that fit both of these categories, and my two favorites are:

The Grande Fanny: Hands down, the only “everyday” purse I’ve used pretty much since I purchased it over two years ago now. I will rotate out the straps based on my outfit (a nylon strap for casual wear and the thin leather strap it comes with for a more elevated look–like when we’re going out, for example).

It’s the ideal mom bag–holds several snacks, a mini pack of wipes, etc, and is ideal for travel–holds just the right amount of stuff with a tiny footprint and always ensures you stay hands free AND look stylish doing it!

I have the cream rattan and I wear it year-round, but have been lusting after the green FOR FOREVER as well.

The Woven Bando: (Pictured below) Newest to my collection, this is now my favorite tote bag. It holds everything I need (my 13” MacBook, notebook, snacks, water bottle) but isn’t big and bulky. When we go out to dinner, I can throw enough activities inside to keep June busy, yet I don’t feel annoyed like I would hauling a giant tote or backpack to a restaurant. I LOVE the chic black and white pattern, and again, I think it makes every outfit look way cooler. SO much more interesting than the “classic black tote.”

Outfit links here

Cool sweatshirts:

My style has gotten SO much more casual since becoming a mom (and also since 2020–the WORLD in general, I feel, has become significantly more casual)–which means, the backbone of my closet= sweatshirts.

But not just ANY sweatshirts–I love COOL sweatshirts. Cozy, comfy, but stylish and intentional. Sézane and Clare V (like the one I’m wearing above) are some of my go-tos for cute, elevated sweatshirts, but I also adore GAP’s vintage-inspired logo sweatshirts (I just got this one and I’m OBSESSED and wearing it as we speak!)

I love pairing them with jeans and some cool, fun sneakers (I love my silver J.Crew sneaks from last year–now on sale! I wore them all over London!)

Fun but comfy footwear:

Metallic sneakers: Speaking of, I love my silver sneakers, as mentioned above. They go with everything but add a lot more interest than a classic white sneaker does! (I still love a classic white sneak, don’t get me wrong!) The J.Crew version I have are WILDLY comfortable. There are so many other cute versions out there too–like these, these, or these!

Fun flats: I have a mesh pair of ballet flats from last year that I wear all the time–(can’t link them anymore but similar here, here and here!) I love that they are the summery version of ballet flats (because regular leather flats feel too hot for summer weather!) Also…

JELLIES! these fun jellies from GAP are my newest shoe purchase and they are SO fun. Wore them shopping over the weekend and they were very comfy.

Clogs: I found these Swedish leather clogs on Amazon, and while I don’t wear them THAT often because I don’t have an occasion to, I love them. They’re so fun and funky and I wear them when I would often wear “heels.”

I also have some really old ugly-cute Reef slingback clogs that I love–which they no longer make (similar here though!) but the Rothy’s clogs I’ve had my eye on for so long, and you all rave about!! Again, ugly cute, but that’s part of the art teacher charm, no!?

Baseball caps:

This isn’t new information, as you’ve seen me wearing baseball caps for YEARS now, but for the newbies–I couldn’t leave this out. Some people have the messy bun, I have the baseball cap. I personally think it’s more practical (hello, disguising unwashed hair) and also makes your outfits look more intentional (a cute accessory!)

I know baseball caps aren’t for everyone, but if you want to give them a try, I have owned and loved this minimalistic Amazon baseball cap for YEARS. And it goes with everything. (From my minimalist staples to my kookie art teacher ones. Obviously we love a basic that goes with it all!)

BUT, if we want to talk more dopamine dressing–I also love (again, go figure) Clare V’s baseball caps for a fun way to make your everyday outfit into a statement.

(“In THIS economy?” you say) I will FULLY admit that spending $70 on a baseball cap is not normal behavior HOWEVER–I do wear my funky Clare V baseball cap all the time, so the cost per wear is now pennies, it brings me SO much joy, and also, she’s a small business and I love supporting a small woman-owned biz (where much of her stuff is made locally in LA when possible). Do with this what you will!!

Oversized button-downs:

Another thing that isn’t new to me whatsoever, but I felt worth listing here because, like sweatshirts, these are also another workhorse of my wardrobe and I have really been enjoying acquiring them in fun striped color ways and oversized fits.

My #1 tried and true is the Sezane Max shirt–which I wear almost weekly in the denim colorway, but they have so many more fun colors and patterns now! Plus, I think a fun way to experiment with color or pattern is in a classic silhouette that you’re already familiar with, styling it how you normally would–another reason the button down is a big winner in my book.

Also–I really like wearing an oversized button-down as a second layer. It’s great for cool mornings, evenings, and in-between weather. Layers=interest, so throw it over a cute graphic tee, over an athleisure top (these are my favorite from Amazon) to elevate your bike shorts, layer one underneath overalls for a fun juxtaposition of styles–these add a lot more personality, especially in a fun color way!

and speaking of button-downs…

fun poplin set I just got from Gap

“Keep it Cool” set from Free People

Fun matching sets:

A great two-for-one special? A matching set that you can mix and match with other tops and bottoms! (But mostly, I like wearing them as sets!) I’ve been really drawn to them in brighter colors.

Button down sets: I absolutely adore (and live in) matching sets like this fun poplin set I just got from Gap for the summer. (Or this gauzy set from Amazon I have owned and loved for years now.) Also, this gauzy one from GAP–I love the silhouette of the pants, the breezy gauzy material, and these also come in fun colors!

Breezy Free People sets: Also fits perfectly with the art teacher vibes–flowy, the “Keep it Cool” set from Free People has become a staple of mine since last summer. I own it in two colors!!

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Have you noticed your personal style shifting lately? Or maybe ITCHING to shift? What have you been drawn to? What feels most authentic? Any auntie-approved staples we should know about!?

Thanks so much for reading and I hope you have a wonderful rest of your week!

Love,

Jess