Both our girls are in school this year, which, for me, means the return of routine and, as such, the return of getting dressed. No more spending the whole day in athletic clothes in anticipation of a workout that doesn’t actually end up happening until 9pm. Instead, I’m trying to move my body first thing in the morning — or at least as soon as possible post-drop-off — so that I can spend the rest of the day tackling my to-do list with intention. And that kicks off with putting on Real. Actual. Clothes.
3 Simple Outfit Formulas For Looking Pulled Together Without Trying Too Hard
While I want something a bit more inspired than what “mom outfits” might bring to mind, we’re still talking easy and approachable. I will not be showing up to pickup a la Carrie Bradshaw in a tulle skirt (although, I do have a tulle skirt that is pretty dope dressed wayyyy down…) but in simple, realistic outfits featuring a few workhorse pieces that hint at the involvement of effort.
To that end, here are three favorite casual fall outfits I’ve had in rotation lately. And since each one is more or less a formula, the same gist can be repeated over and over again all season long.
Fall Outfit 1: Dark Wide Leg Jeans + Fitted Henley + Saddle Bag
jeans (TTS unless you tend to be between, then size down — more washes here) | tee (s) | similar shoes | similar bag
These days, dark jeans like this feel almost too glam on me unless they’re paired with something unapologetically casual up top. But for times when I still want to lean into a more polished look, a fitted henley tucked into a high-waisted pair of dark denim is unbeatable. It leans more ’70s than early ’00s, and putting a little saddle bag with it (and a pair of vintage suede heeled sandals) pushes the vibe even further.
jeans (TTS unless you tend to be between, then size down — more washes here) | tee (s) | similar shoes | similar bag
These jeans are some of the best I’ve bought in a long while. They’re absurdly comfortable, even with the high rise, and buttery soft thanks to a lyocell/cotton blend that isn’t stretchy but has plenty of give. I’m wearing my true size, but if you’re between, I’d size down one. More washes here with lotsa sizes, too.
And the fitted henley is good enough that I picked it up in a second color. It’s stretchy and just thick enough and subtly sexy in a tomboy kinda way. Absolute perfection. Linking up a few more options I love below, too.
More Fitted Henleys and Saddle Bags I Love
Fall Outfit 2: Distressed Baggy Jeans + Oversized Denim Bomber + Flats
jacket (s) | similar jeans | flats (tts) | similar tee | similar vibe bag
I wrote an entire ode to this jacket in this post. It is perhaps my most worn item in all of 2026, which says a lot since I’ve only had it for two months now. I throw it over everything — a workout set for drop-off, pajama pants and a hoodie when I take the dog out in the morning, jeans and a tee (a la the outfit you see here), breezy dresses — and it instantly makes everything look interesting and styled.
The weight is ideal for putting over tissue-thin tees or chunky sweaters layered over long-sleeve knits, and because of its oversized fit, nothing is tight or constricting. Honestly, this post could have just been photos of me wearing this jacket over everything, every day for the past six weeks. It’s the piece defining my style this season.
jacket (s) | similar jeans | flats (tts) | similar tee | similar vibe bag
My jeans are from long ago, but since distressed baggy jeans are having a bit of a moment again (absolutely zero complaints here), I’ve linked up some very similar options below, with a few different rise options, too.
I love the idea of pairing several oversized pieces together (I blame the Olsens), so most mornings I reach for a big ol’ graphic tee, but you could also go a little Gen Z and pop a tinier top with the big jeans and big jacket.
And never underestimate the power of a sleek ballet flat to elevate the most casual of outfits. Remember the whole Wrong Shoe Theory of 2020? Still holds up.
More Distressed Wide Leg Jeans and Ballet Flats
Fall Outfit 3: Barrel Overalls + Striped Tee + Loafers + Hobo Bag
overalls (s) | tee (boys XL) | bag (current colors and here)
I’ve been making an intentional return to my The Sak hobo bags, too, of late. They’re really ideal as a Mom bag — just schlep it all in, they hold an ungodly amount of random crap — but they always look chic and a little nostalgic. Very ’70s by way of the ’90s. There are new ones in new colorways always being released, and loads of them on eBay.
overalls (s) | tee (boys XL) | bag (current colors and here) | loafer mules (TTS)
It’s almost embarrassing to admit how many pairs of overalls I own — *and actually wear* — but these overalls from Free People are easily the ones I reach for most often. The barrel fit isn’t too over the top, but it adds a little extra something that prevents them from feeling too…farmer-y? Striped or graphic tees add playfulness (this one is both — and, full disclosure, from the little boys’ department), and then if I want things to feel a little more interesting, the Wrong Shoe Theory applies perfectly here, too, with a pair of loafer mules, though I’m just as likely to add flip flops, Boston clogs or sneakers to this outfit, as well.
Linking up a couple of other favorite overalls below, plus some tees I just can’t resist.
More Graphic Striped Tees and Overalls
Cheers to a new season of Getting Dressed, gang.
xo,
Em
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