30 Days of Outfits to Kick-Start Your September

There's just one long weekend between us and the start of September and a whole new season of outfits. While that's always something we look forward to, it doesn't come without its challenges — there are only so many days we can wear our jeans without getting bored, right? To prevent that from ever happening, we've tapped a few of our favorite street style stars and come up with 30 looks, one for every day of the month ahead. Can you feel it? We can tell already, it's going to be one very stylish September. Scroll through to get all the inspiration you need.

Fall Street Style
IMAXTREE | VincenzoGrillo

Fall Street Style

Cap off your casual look with a quintessentially cool varsity jacket to beat the chill in style.

Fall Street Style
Greg Kessler

Fall Street Style

A button-down is all business up top, but a slit pencil skirt makes it a bit more party on the bottom.

Fall Street Style
Greg Kessler

Fall Street Style

Why not dress up denim with a great coat and sleek boots?

Fall Street Style
Greg Kessler

Fall Street Style

Caroline Issa pepped up her black and white trousers with print for an easy albeit elevated look.

Fall Street Style
Le 21ème | Adam Katz Sinding

Fall Street Style

Never underestimate classics, like a great pair of trousers and pumps.

Fall Street Style
Greg Kessler

Fall Street Style

Digging the denim and leather look, always.

Fall Street Style
IMAXTREE

Fall Street Style

Giovanna Battaglia dressed down an LBD with leopard-print flats, making it a totally approachable look for work and play.

Fall Street Style
Greg Kessler

Fall Street Style

A pop of plaid and a little distressed denim are made for each other.

Fall Street Style
IMAXTREE

Fall Street Style

We love when Fall rolls around — so we can start wearing our boots with our dresses again.

Fall Street Style
Greg Kessler

Fall Street Style

There isn't a thing we don't love about this retro-darling look.

Fall Street Style
IMAXTREE | VincenzoGrillo

Fall Street Style

Elena Perminova's modern formula for updating the cardigan? Add skinny jeans and statement jewels.

Fall Street Style
IMAXTREE | VincenzoGrillo

Fall Street Style

Sarah Rutson perfected the sophisticate's play on leather in a pencil skirt and a cropped trench.

Fall Street Style
Le 21ème | Adam Katz Sinding

Fall Street Style

Take note and let your pants be the statement piece.

Fall Street Style
IMAXTREE

Fall Street Style

Joanna Hillman has the perfect way to add a punch of color with a bright bag.

Fall Street Style
Le 21ème | Adam Katz Sinding

Fall Street Style

Embrace the ladylike dress code with a calf-length skirt; then give it the coolest kind of finish with just your shades.

Fall Street Style
Greg Kessler

Fall Street Style

Christine Centenera perfected the art of sophisticated seasonal dressing in a sleek skirt, a little sheer, and just the right accessories.

Fall Street Style
Greg Kessler

Fall Street Style

All black looks chic, anytime, anywhere.

Fall Street Style
FameFlynet

Fall Street Style

Even tailored shirtdresses feel instantly casual with the right finisher. A two-toned jacket on model Liu Wen made for a sporty, easygoing vibe that would still work at the office.

Fall Street Style
IMAXTREE

Fall Street Style

Juxtaposing a little embellishment and leather is the perfect way to ease into the cooler months.

Fall Street Style
IMAXTREE | VincenzoGrillo

Fall Street Style

Shiona Turini's laid-back look came with a moto jacket and a knit pencil skirt — certainly worth replicating.

Fall Street Style
Greg Kessler

Fall Street Style

Taylor Tomasi Hill knows that there's more than one way to wear a scarf — a valuable lesson to inspire your Fall styling.

Fall Street Style
Le 21ème | Adam Katz Sinding

Fall Street Style

This season, get ready for the return of minimalism — crisp black-and-white palettes and easy pieces.

Fall Street Style
Le 21ème | Adam Katz Sinding

Fall Street Style

Colorblock trousers in supercontrasting shades are guaranteed to catch the eye.

Fall Street Style
Le 21ème | Adam Katz Sinding

Fall Street Style

Easy Autumn days call for easy styling — like a skirt finished with slip-on kicks.

Fall Street Style
Greg Kessler

Fall Street Style

Proof that simple can be simply stunning; just throw your favorite sweater over a slip dress for effortless Fall dressing.

Fall Street Style
IMAXTREE | VincenzoGrillo

Fall Street Style

Olivia Palermo perfected the classics in a powder-blue skirt and a button-down.

Fall Street Style
IMAXTREE

Fall Street Style

Take a cue from Sarah Rutson and play it ladylike in shades of navy and black.

Fall Street Style
Greg Kessler

Fall Street Style

Emmanuelle Alt proved that you don't need an army of statement pieces; sometimes, just your favorite jeans and a great button-down will do.

Fall Street Style
Greg Kessler

Fall Street Style

Julia Sarr-Jamois helps answer any lingering questions about how to wear sneakers right.