What I’m Wearing To Drop-Off This Fall (aka These Levi’s Are So Good I Almost Kept Them To Myself)


This post is sponsored by Macy’s and Collective Voice.

So, first off, I know. A school drop-off post? Was it not just Memorial Day? Trust me. This is throwing me off just as much as you.

Not to mention the fact that we’ve had one of the grayest summers yet in Half Moon Bay. Like, that can’t possibly count. I’m not ready to re-enter this headspace, and yet here we almost are. Oof.

But second: these jeans.

My fave way to look intentionally dressed at school drop-off? Levi's baggy jeans + a graphic tee + a crochet bag (all from Macy's!) for a cool '90s style.

jeans (25) | tee (S) | shoes (TTS) | bag

I’m gonna talk about the whole outfit because it’s one of those updated “if it ain’t broke” situations that I swear by, but the jeans (spoiler alert: They’re completely new-to-me Levi’s!!) just have me all sorts of excited, so we’re starting there.

The Secret Is Out: Levi’s Baggy Jeans Are Too Freaking Good (& Easy To Style)

1 of my fave hacks to looking semi-intentionally dressed at school drop-off is to start with a pair of jeans in a current silhouette.

jeans (25) | tee (S) | shoes (TTS) | jacket (XS) | bag

I’ve said it before: One of my favorite hacks to looking semi-intentionally dressed at school drop-off is to start with a pair of jeans in a current silhouette — something full length with a little volume — and then top it however your little tired heart desires.

And, friends, I can’t imagine better jeans for the job than these Levi’s Mid-Rise Cotton 94 Baggy Jeans.

I can't imagine better jeans to wear in a casual yet put-together outfit than these Levi's mid-rise jeans.

jeans (25) | tee (S) | shoes (TTS)

They are, quite frankly, so dang good — with a feel and fit that look like a genuine vintage score — that my first reaction was to audibly exclaim “getthefrickout!” while grinning so absurdly at myself in the mirror that you’d swear I’d been body-snatched by the Cheshire Cat.

But my next thought was maybe even more telling because it was something like: Holy crap, maybe I should keep these to myself.

I wanted them to be my secret jeans, gang. I mean, I could probably end this blog post right there.

But I need you to know more.

My fave way to look intentionally dressed at school drop-off? Levi's baggy jeans + a graphic tee + a crochet bag (all from Macy's!) for cool '90s style.

jeans (25) | tee (S) | shoes (TTS) | bag

Levi’s has released all sorts of updated denim styles over the past year or so, and I’ve honestly been so overwhelmed that I’ve mostly just stayed safely huddled in the comfort of my 501 bubble. But when I saw these Levi’s 94 Baggy Jeans on the Macy’s website the other day, I couldn’t look away.

** PS – scoop up more great deals on back-to-school denim, graphic tees, jackets and more at Macy’s (ends 7/23) **

These Levi's mid-rise jeans have a higher, slightly contoured waist & a roomy straight leg that's surprisingly elongating.

jeans (25) | tee (S) | shoes (TTS) | bag

The vibe is everything I love about a hip-slung pair of borrowed 501s, but with a higher, slightly contoured waist and a roomy, full-length straight leg that’s surprisingly elongating. They look both modern and vintage, and something about the experience of finding them through Macy’s — where I spent countless hours back-to-school shopping and scouring the sale rounders as a pre-teen — made the whole experience feel very full circle.

(Truly, if ’94 Emily knew this blog post was taking place, not only would she be 100% on board with the jeans, but I also think her mind would be just a little bit blown. Sometimes this eccentric gig of ours is pretty dang cool.)

OK, let’s dive into a few more details.

A Fresh Take On ’90s Style: Levi’s Baggy Jeans + An Oversized Graphic T-Shirt

So, drop-off uniform recap: A current pair of jeans topped off with just about anything of your choice instantly gives I’m putting in the effort to get dressed and even I’m a little bit fashiony. Easy.

In this scenario, I kept things as foolproof as possible — jeans and a graphic tee — with a little bit of a ’90s twist. (Do we get bonus points if we lived through these trends the first time and are still voluntarily donning them again? I think yes.)

Levi’s Mid-Rise Cotton 94 Baggy Jeans

The full length of these Levi's 94 Baggy Jeans makes them feel current & look elongating.

If you’ve made it this far, you already know that these Levi’s 94 Baggy Jeans have me feeling some kind of (very good!) way. They’re a bit like barrel-jeans-married-dad-jeans but with a better butt than either of the two would suggest.

The full length makes them feel current and look elongating, and, unlike some of the high-waisted wide-legs and flares that I love, it’s just fun wearing longer jeans that don’t necessarily require platforms or heels for maximum impact. (That said, I can’t wait to play around with dressing these up.)

I love the soft (read: not overly stiff) 100% cotton composition of these Levi's mid-rise baggy jeans.

I love the soft (read: not overly stiff) 100% cotton composition too. I’m 5’5″, and I’m wearing my usual size 25 in the medium wash (there are several others, including a washed black that is very tempting). The inseam is 31 inches, which allows them to break generously over sneakers. And while Levi’s calls these mid-rise, I’d say they’re mid-to-high on me. My guess is that many of the models on the site are wearing a size up for a looser fit.

Cotton On Boyfriend-Fit Guns N’ Roses T-Shirt

This graphic tee from Macy's is heavier than a tissue-thin vintage T-shirt, but still broken in with an easy drape.

In keeping with the ’90s vibe, I paired my baggy Levi’s with an oversized Guns N’ Roses tee from Cotton On (who knew Macy’s carried Cotton On?), which, unsurprisingly, does cotton graphic tees really well. The weight of this one is perfect. Heavier than a tissue-thin vintage tee, but still broken in with an easy drape. This feels like a tee you’d pay triple digits for in a vintage boutique, so the fact that it’s under $30 makes it feel a bit like you’re getting away with something.

Maybe best of all, it holds up really well to washing. Wearing a small here, and while I could have gotten away with an XS, the exaggerated sizing makes it really versatile. (Untucked, it’s almost tunic length and is excellent with leggings or swishy wide-leg pants.)

Levi’s Ex-Boyfriend Cotton Denim Trucker Jacket

If you want to lean in to the oversized trend, size up 1 in the Levi's Ex-Boyfriend Denim Trucker Jacket

I have Levi’s Ex-Boyfriend Denim Trucker Jacket in a classic denim wash, and it’s something I’ll own forever, but the ivory is a fun departure and an easy outfit-maker when you don’t want the denim-on-denim thing. Wearing an XS here; I’d say if you really want to lean into the oversized trend, you could size up one.

The Sak Limited Edition Crochet Ashbury 120 Hobo Bag

The size of this crochet hobo bag from The Sake is great for stashing the essentials & then some.

Talk about timeless. I worked in the Macy’s ladies’ shoe department in college, and I have such a clear memory of looking across the way at a rack of softly shaped The Sak hobo bags and thinking how their pretty teardrop profile felt so iconic.

The Limited Edition series of this Sak 120 Crochet Hobo is incredibly well made: The 100% recycled poly is hand-crocheted by female artisans in Bali, and it is flawless; there’s a sturdy lining; a zippered pocket both inside and outside; two stash pockets; and a strong magnetic closure.

The size is great for stashing the essentials, and then some. (For drop-off mornings, that means keys, phone, sunnies, cards + lip balm, plus I almost always have a reusable shopping bag and the babe’s water bottle and snack in tow in case we end up heading off to errands after.)

Seasonless too, and also available in black.

Converse Chuck Taylor Madison Low-Top Sneakers

These Converse Chuck Taylor low-top sneakers have a cushy insole & a padded collar + tongue.

I geeked out hard over these Chuck Taylor Madison Low-Top Sneakers when they arrived. Classic Chucks styling, but with a slightly lower profile that makes them subtly feminine. Plus, they have a cushy insole and — wait for it — a padded collar and tongue that’s so much easier to wear than stiff canvas (and makes it really easy to prop the tongue forward for a looser look and slip-on functionality). True to size — unless you’re between, and then I’d size down.

Here’s to making my secret jeans your secret jeans (whether school drop-off is on the agenda or not).


Big thanks to Macy’s for sponsoring this post. I’ve said this before, but I have such a soft spot for Macy’s. It’s where I grew up shopping with my mom, where I honed my math skills calculating promotional discounts, where I opened my first store-brand credit card, and even where I had my first retail job. I so appreciate the opportunity. ❤️ And if you’re reading along, thank you for supporting the brand partners that allow us to keep doing our thing. We’re so glad you’re here.

Friends! Follow me on Instagram for accessible, easily adaptable recipes; sneak peeks of The Mom Edit content (and sales!); and more snippets of our life on the Northern California coast. And if you feel so inclined, pop over to my personal food + lifestyle blog, The Pig & Quill, where I share salty scribblings from my kitchen and home life. Byeeeeee!

Photos by Carolyn Stockman. Thanks, friend!

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My fave way to look intentionally dressed at school drop-off? Levi's baggy jeans + a graphic tee + a crochet bag (all from Macy's!) for cool '90s style.

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