Guyyyysss….what the heck are we actually going to wear this fall? Or maybe – more accurately – what the heck do we want to wear this fall? Ignoring, for the moment, the hot weather outside. Obviously. But in Philly our nights are getting cooler (I actually needed a jacket walking home from the office last night!) and Pax is already starting to talk about Christmas (no apologies, I am WITH HIM) and so here I am: just a girl staring into her closet, searching for shades of brown. So I went through the fall 2026 fashion trends, messed around with a bunch of them, and pulled together a short list of outfit combinations and pieces – based on these trends – that are the best combination of fresh and doable.

Oh and Happy Pumpkin Spice Latte, to those who celebrate.

Fall trends this year look especially exciting: silk duster coats! Maximalism! Fringe! My life, however, looks remarkably less exciting: making lunches! lifting weights! working from home!

So. I will….probably skip the silk duster. Probably. Admittedly, that one is fabulous – I just need a reason (someone give me ONE reason!!).

Anyway, let’s get into the fall trends and/or fall pieces and/or fall outfit combos I’m actually wearing this fall. Because a girl’s gotta share what works, ya know? Gatekeeping sucks.

GAP | Madewell | Guest In Residence

Ok! These are a FAR CRY from the silk duster, but I just ordered those GAP pinstripe pull-on pants in gray. AND – now this is the exciting part – I WILL WEAR THEM INSTEAD OF SWEATPANTS. Tadaa!! If I’m feeling really wild and crazy, those Madewell plaid pants – 90’s loving girl that I am – would be a step up from there.

To style: picture any of these bad boys with some sort of sporty top or t-shirt, with colorful & cozy striped sweaters, and, occasionally, with a little lace cami. Here’s my interpretation:

baseball tee (m) – also in red | pinstriped pants (m, petite) | bag | ring | earrings

These sweatpant replacements will work with all of the comfortable shoes I’m already into this fall (mainly ballet flats, honestly), but they’ll also work with cool, low-profile sneakers and even UGGs. My sexy mesh ballet flats will definitely be in high rotation (2 years running!!), and these pants are one reason why.

Revolve | GAP

Yup yup yup – 90’s again, and I couldn’t be more thrilled! I don’t know that one must buy a pre-layered tee (although both above finds are seriously cute)…I’ve just been layering my existing tees over each other and it all seems to work out.

Style tip: Don’t be afraid to layer a tee over a collared button-up shirt, too. Similar vibe, slightly more polish, very cool.

And I am constantly searching for ripped jeans. I have loved these forever and ever – I’ve never really stopped wearing ripped jeans – but when they’re trending, it simply means we have more choices. I also love – if rips are too much – a perfectly broken-in, stole-from-your-boyfriend, light-ish-but-not-light wash.

Frēda Salvador ballet flats | matching bag

What does Fall’s baggy jeans, easy pull-on pants, and layered tees all have in common? They’re all really, REALLY casual. And an outfit that consists of oversized, casual jeans + big, casual tops can sometimes feel sloppy instead of cool. So one of my favorite styling tricks is to intentionally match my shoes and bag. This matchy-matchy combo can look a little prissy with a “nice” outfit, but with an uber-casual one? It’s freaking perfect.

sweatshirt (xs/s) | jeans (29) | ring | Frēda Salvador ballet flats | matching bag

And while this styling trick works even with a black shoes/black bag pairing, it’s even better – and by “better” I mean that it’s more of an intentional statement – when the shoe/bag combo is something statement-making. Plaid or prints will obviously work, or maybe some unexpectedly fun colors, too. And I don’t think the shoe-bag combo has to be a perfect match, it’s just gotta look intentional, rather than accidental.

LEFT: polo (m) | culottes (30) | brown boots | tote | ring | necklace | earrings
RIGHT: tee (s) | culottes (29) | sneakerinas | bracelet

I am…[takes deep breath]…SO EXCITED about culottes. They can be styled in very similar ways to my baggy jeans, but it’s an opportunity to show off shoes that otherwise get lost. And the culottes + boots pair is one I’ll be rocking WELL into fall/winter.

If interested, we rounded up our favorite pairs of culottes, here, or, if you’d like some styling advice, we also created a downloadable guide with 6 Easy Ways To Style Culottes, with plenty of late-summer, early-fall inspo.

LEFT: Sézane
RIGHT: leather jacket (s) | jeans (29) | shoes | bag | ring

A shorter, blouson-style jacket – rounded throughout, cinched in at the waist – is the BEST jacket style to wear with long, loose denim styles. Whether you’re into baggy jeans, barrel jeans, a looser pair of wide-leg jeans, or even culottes…a jacket that cinches in at the waist helps to create shape and keep the outfit from being too overwhelming.

Even better? Because of the cut, many of these jackets will ALSO fit over bulky sweaters nicely, making them an easy win even into winter.

I’m really into the leather or suede versions of these jackets, but I’ve also found some stunners in canvas, too. Bonus points for details like funnel necklines (another micro fall trend, although not necessarily the important part of the jacket) and cool sleeve details.

Anthropologie | Aritzia | Doen

Remember when, once upon a time, we all were wearing faux-leather leggings to holiday parties? (Scotti, this was you!) I think this is the cooler equivalent for 2026/2027. I love the lace-trimmed ones now with sexy little sandals, ballet flats, and strappy heels…but I think they could look really good this winter with a sleek ankle boot, too.

For holiday parties, I will likely style these with my favorite cropped cashmere sweater because I am boring like that. (Hmmm…maybe THIS outfit needs a silk duster??)

For more, we rounded up our favorite pairs of balloon pants here…and yup: our latest guide has 6 cool ways to wear balloon pants for early fall.

GAP denim bag | Sézane canvas bag | Parker Thatch Heritage leather bag | Miu Miu Vivant Leather Bag

There are a ton of seriously cool bags out this fall, but the trend that’s really caught my eye is what I’m calling the “casual heirloom” trend. It’s classic, vintage-inspired bag silhouettes crafted from a really broken-in, well-loved leather (or a leather meant to be broken-in and well-loved) or – and this is exciting because it makes this trend incredibly affordable – crafted from a surprisingly casual fabric: canvas, 100% cotton, or denim. The result is a totally modern (yet nostalgic!) bag, and I LOVE it.

Obviously, this is the best trend to find in a second hand or vintage store, but there are a few designers coming out with bags that might be worth the splurge (aka they’ll last forever). That said, if you have your eye on the more affordable canvas or 100% cotton/denim iterations, those are selling out, like, immediately. Sezane’s canvas bag collection sold out in days (they are restocking with new styles), as did GAP’s 5 Pocket Tote Collection. In both cases, you can add yourself to a wait list (totally worth doing, imo).

boots

Boots…are tricky. And tall boots, I find, are the trickiest. Tall boots often skew very polished, very put-together – especially if heels are involved – and typically pigeonhole an outfit into the “dressy” category. Which, if you haven’t yet caught on, is not my usual style. Moto boots are great but heavy (both visually and, like, literally), and I’m not a girl willing to walk around all day in rainboots.

But tall, flat, plain boots? THESE are boots I can work with. And this fall, they seem to be everywhere. Here’s how I’ve been wearing mine:

LEFT: sweater (m) | culottes (29) | boots | bag | ring | waterproof hoops
RIGHT: tee (s) | skirt (m) | boots | bag | ring

This style of boot is great with skirts, great with culottes, and, if you stick to a pair in some sort of beige/tan/brown suede, they go with everything, too. These are basically the winter equivalents of ballet flats (and you can wear them with basically everything you’ve been wearing ballet flats with, too).

My favorite boots for fall are flat, have a bit of a pointed or square-shaped toe, and a minimal sole. Not only does this strike me as a pretty fresh look, but these boots are lighter in weight, too, and I find them more comfortable to wear.

That said, chunkier boots with sturdy, wood-based bottoms (like Frye’s classic campus boots) can also work – they’re still very much in the ‘tall plain boot’ category – but they’re visually (and physically) heavier.

What are you guys excited to wear this fall??

xo,

S