30 Perfect Looks To Copy This September

Photo via @manrepeller.
September in New York City is, well, kind of the dream. Weather-wise, we tend to get the best of both worlds — remnants of hot summer sweat, and a first-look at crisp autumn days — which can make for some serious sartorial creativity. So, how do you (and your wardrobe), balance two seasons at the same time?

The answer is simple: keep your options open, because you can easily go from rocking shorts and an off-the-shoulder top one day to a turtleneck and palazzo pants the next. And while the temperatures may be tricky to predict, looking good all month long isn't. From lots of layering to go-to transition pieces, we've rounded up 30 killer outfits to emulate this September.
1 of 30
Photo via @alealimay.
Give your classic shirtdress an upgrade by opting for one that has some variety of embellishments or detailing — it's the ultimate workday staple, after all.

Cartier necklace.
2 of 30
Photo via @chantagold.
If you haven't hopped on the '70s style bandwagon, next season is the perfect time to stop fearing the wide-legged pant. Bell-bottoms have never looked so good — seriously.
3 of 30
Photo via @eggcanvas.
Get creative with your outerwear (since it's bound to play an integrative part of your wardrobe this fall), by switching up your go-to leather jacket for a playful, printed bomber.

3.1 Philip Lim jacket, Isabel Marant Étoile dress, Céline sunglasses.
4 of 30
Photo via @fashionindie.
Two variants of the same pattern can make for perfect coordination — rather than clashing.

AGL shoes.
5 of 30
Photo via @girlnatalie.
When tights season rolls around, become a layering pro by pairing your favorite summer frock over a simple t-shirt and cropped, flared, frayed jeans.
6 of 30
Photo via @hannahbronfman.
This is how you wear a suit to work. Select an unexpected hue (like this light grey), and a cut that's not so structured (but still super-feminine).

Akris suit, Stuart Weitzman shoes, Jennifer Fischer necklace.
7 of 30
Photo via @hauteinhabit.
It's not time to retire your favorite white frock just yet. F*ck the "no white after Labor Day" 'rule' by taking a summer dress into the next season, and pair it with a leather jacket, and heeled booties.
8 of 30
Photo via @jennyalbright.
Look to athleisure (think a simple tank and comfortable kicks) on those days you just don't feel like trying.
9 of 30
Photo via @jourdansloane.
Let the off-the-shoulder trend continue as the weather changes by opting for a long-sleeved version. Pair it with leather booties and a chic mini for maximum cool.

Zara shirt, Theory skirt, Chanel bag, Alexander Wang shoes.
10 of 30
Photo via @julianasalazar.
Wide-brim hats aren't just for laying by the pool. In fact, with the right styling, it can look as good with a bathing suit as it does with a varsity jacket and a flowing skirt.
11 of 30
Photo via @jxxsy.
Let your favorite early-aughts polo shirt make a comeback in a big way. The more colorful, the better, along with wider pants to pair it with.

H&M pants, Michael Kors bag.
12 of 30
Photo via @kaiaventdeleon.
Don't shy away from experimenting with metallics — whether it's a subtle pop or the whole damn look.
13 of 30
Photo via @le21eme.
We have officially found our dream fall look: a suede, front-tie maxi-dress, and the most awesome pair of fringed heels.
14 of 30
Photo via @lexierenee.
Three words: layer, layer, layer. Take your go-to mom jeans and fall booties to new heights with creative styling, like trading in the usual sweater or T-shirt for a bodysuit and oversized vest.
15 of 30
Photo via @madebymalyia.
Because some September days are bound to be hot, keep your favorite peasant top and flowing midi-skirt near by.
16 of 30
Photo via @manrepeller.
Proof that sometimes more is better. Can't decide between a playful bag, choker, or hat? Just go for it and pile it all on.

Janessa Leone hat, Delfina Delettrez necklace, J. Crew shirt, Valentino skirt.
17 of 30
Photo via @marcosfecchino.
A simple white button-down and flared jeans get a more grown-up appeal when paired with a bomber jacket and printed platforms.

NYDJ shirt and pants, Jonathan Simkhai jacket, Tom Ford shoes, Dannijo jewelry.
18 of 30
Photo via @marigiudicelli.
'Tis the season for trench coats, so why not rock yours as a full-on dress?
19 of 30
Black-based florals can make even the daintiest and most feminine of frocks feel seasonally-appropriate. Layering with multiple jackets (which can actually make an entire look) is not required, but definitely recommended.

Club Monaco blazer, J.J. Hat Center hat, Moscot sunglasses.
20 of 30
Photo via @nadiafairfax.
Yes, your favorite silk pajamas can definitely double as a cocktail dress. All it takes is the right pair of shoes.

Tome dress, Francesco Russo shoes.
21 of 30
Photo via @natgeorgala.
In a sea of blacks and browns, add some color to your wardrobe next season with some bold shades of blues or greens.

Stefanel shirt and skirt, Kokkoris Optics sunglasses.
22 of 30
Photo via @paridust.
Loose, wide-legged boho pants are a simple, sleek way to keep (and look) cool.

Karie Lacks shirt, Anna Sui pants, Mizuki necklace.
23 of 30
Photo via @quistyle.
Sick of your same old blouse? Switch things up with a kimono-style wrap top. Pair with a maxi-skirt and classic Converse for the ultimate in comfort and style.
24 of 30
Photo via @racheletnicole.
So low-maintence (and so awesome), a pair of overalls might just become your wardrobe BFF come fall.

Boohoo overalls.
25 of 30
Photo via @saintrecords.
Proof that you can never have too many statement-making pieces.

Rachel Comey shirt, Tibi pants, Malone Souliers shoes.
26 of 30
Photo via @tavitulle.
Separates in light loose fabrics are the key to beating those awkwardly warm autumn days.
27 of 30
The retro, hippie-style look is here to stay (thankfully), and a loose, long-sleeved floral frock (with some killer lace-up sandals) make for a sweet '70s pairing.

Chloé dress, Chanel bag, Emilio Pucci sunglasses.
28 of 30
Photo via @thegreylayers.
The versatility of a jumpsuit is something we're lucky translates to all seasons. Whether it's wide-legged, high-necked, or sleeveless, there's tons of variation for everyone — and every type of weather.

English Factory jumpsuit.
29 of 30
Photo via @weworewhat.
Forget all black everything. This season, dare to be different and keep things on the lighter side — literally — in an unexpected, fully-white ensemble.
30 of 30
Photo via @wolf_nyc.
Trade in your graphic statement tee for a bolder (and warmer) statement-making sweatshirt. The looser and cozier, the better.

More from New York


R29 Original Series