Is it summer? Is it fall? TBH, we're not really sure — and the weather isn't, either. At least, that's what we're predicting for the month of September, which always seems to ride the line between super-sticky, sweaty, and hot (though we're still raising those prayer hand emoji for a few more weeks of sun) and crisp, breezy, and ideal for finally breaking out that new jacket we bought before it was actually cool enough to need.
Since the temperatures are likely about to bounce back and forth, you'll need a wardrobe that matches. Ahead, you'll find 30 outfits (one for every day of the month) that offer up a ton of variety. From sundresses to leather jackets, you'll be prepared for whatever transitional weather gets thrown your way.
A leather jacket — real or faux, it's up to you — is probably the most versatile (and, frankly, useful) piece you can have in your fall wardrobe. If you're sick of the same black option you've worn to death, switch things up with a more autumnal shade, like brown, navy, or burgundy, or a pattern, like striped detailing or all-over florals. (If you need help, here's a handy guide to finding the right leather jacket for you.)
Photo via @chanchennn.
You know that wrap dress you've worn almost every weekend since May? Make it feel different by layering a sold tee underneath. You've already done that with your slip dresses, so why not do it with this silhouette, too?
Eloquii dress, Isidora Malva bag, Forever21 shoes, Pietra Santa earrings, Breathe Heart Design sunglasses.
Photo via @fatpandora.
Like we've said beofre, the mock neck is the most versatile '90s trend. Wear with cropped jeans and loafers for a more casual look, or dress it up with a miniskirt and block heels.
Frame jeans, Céline sunglasses.
Photo via @alwaysjudging.
Forget the over-the-shoulder jacket or cardigan. This season, it's all about the over-the-shoulder sweatshirt.
Marimekko skirt, New Balance shoes.
Photo via @emilisindlev.
Order a tight-fitting midi dress one size larger than you would normally wear to DIY your own off-the-shoulder neckline.
ASOS dress.
Photo via @asos_debbie.
We all likely have a crisp white button-up in our closets, but how many of us have a longline version that gives the illusion of a dress? See how chic this looks layered over pants?
Frame jeans, Mango bag, Zara shoes.
Photo via @deborabrosa.
Now this our idea of a monochromatic ensemble: Play with two different tones for the main parts of your outfit, and add in some alternately colored accessories to break things up.
Photo via @arpanaraya.
The foundation of a solid transitional outfit is an oversized graphic tee — it's a statement-maker, layering option, and just plain cool.
Vintage T-shirt, BDG jeans, Zara shoes.
Photo via @alyssainthecity.
Tucking your tee into a skirt can feel too polished. Loosen things up by leaving the T-shirt untucked and belting it in the middle. Finish off with sneakers instead of heels, and you've got a look that checks all the boxes.
Topshop Boutique top, Planet Blue skirt, Tory Burch bag, M. Gemi shoes.
Photo via @notjessfashion.
Let's take a moment to admire these three iterations on the simple jeans-and-a-top-outfit. 1. A gray T-shirt, tucked into white jeans, and polished off with leather boots. 2. A cutout shoulder blouse (in a gothic floral print), with frayed hem jeans and netted slides. 3. A long-sleeve tee, cropped flared bottoms, and two-toned shoes. These all look good as-is, or could be mix-and-matched in countless other ways.
Photo via @dilettabonaiuti.
Reminder: Bodycon is no longer strictly reserved for the club. (Plus, we're loving how much this reminds us of Kim Kardashian's VMAs dress.)
The Line by K dress.
Photo via @gabifresh.
That silk slip-over-a-T-shirt may have served you well in spring and summer, but with temperatures dropping, you'll need to find a warmer iteration. That's where the silk cami comes in: Layer over a tee or button-up for maximum coverage, and pair with any pants you please.
Ray-Ban sunglasses.
Photo via @gabrielapelletier.
Because a classic shirt dress will never steer you wrong...
Dior bag, Miu Miu shoes.
Photo via @lisafolawiyo.
...and really, a jumpsuit won't, either.
Carol Callahan jumpsuit.
Photo via @jessicalarez_.
Invest in a trench. You'll thank us later.
Veda dress, Trademark coat, Rachel Comey shoes.
Photo via @lisasaysgah.
Some September days will inevitably feel like the dead of summer. Soak up your last chance to wear that sundress you've been meaning to put on all summer while you still can.
Photo via @atlantabean.
Play with proportions by balancing out a chunky sweater (especially one with extra-long sleeves) with a more form-fitting, lacy skirt and strappy sandals. Fall on the top, summer on the bottom.
Maurie & Eve sweater, J.W. Anderson skirt and bag, Revolve shoes.
Photo via @lucywilliams02.
Earrings are so underrated, especially oversized, dangly ones.
Photo via @tamumcpherson.
Take a cue from Leandra Medine and wear your button-up half unbuttoned. It's like autumn's version of the crop top.
Céline top, Pierre Hardy bag, Chlo é shoes.
Photo via @manrepeller.
The key to wearing a sweater when it's still kind of warm: Pair it with jorts.
Ganni top, Gucci shoes, Ray-Ban sunglasses.
Photo via @mvb412.
Make florals feel more edgy than girly by keeping the rest of the look casual (think: T-shirt and sneakers).
TPDG Supplies Co. top, Gucci bag, Converse shoes.
Photo via @nikejane.
Nothing says throw-on-and-go like a denim dress. Plus, it'll help ease you into wearing jeans again after presumably not wearing pants all summer long.
Stella McCartney shoes.
Photo via @valentinasiragusa.
Hello, multi-layering. T-shirt with a minidress; heeled sandals with printed socks. Why not go all out?
H&M dress, Missoni socks, Zara shoes.
Photo via @reneesturme.
If you needed further convincing that you can 100% wear white after Labor Day, here's proof.
Photo via @vbiancav.
Transition that sundress you've been wearing all summer long into fall in one simple step: Just add boots.
ASOS dress and shoes.
Photo via @asos_lauren.
Track pants and kitten heels might seem like an unlikely combination, but they're actually quite complimentary.
Photo via @stephaniebroek.
Yes, this is a fanny pack being worn as a crossbody, and no, we're not against it even a little bit.
Nike fanny pack.
Photo via @thecurvynista.
If there's one fall trend you should try, it's super-wide-legged bottoms. The volume on these can take any outfit to the next level.
Marques'Almeida top, Acne Studios bottoms, Loewe shoes.
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