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.
Cap off your casual look with a quintessentially cool varsity jacket to beat the chill in style.
A button-down is all business up top, but a slit pencil skirt makes it a bit more party on the bottom.
Caroline Issa pepped up her black and white trousers with print for an easy albeit elevated look.
Never underestimate classics, like a great pair of trousers and pumps.
Giovanna Battaglia dressed down an LBD with leopard-print flats, making it a totally approachable look for work and play.
We love when Fall rolls around — so we can start wearing our boots with our dresses again.
Elena Perminova's modern formula for updating the cardigan? Add skinny jeans and statement jewels.
Sarah Rutson perfected the sophisticate's play on leather in a pencil skirt and a cropped trench.
Joanna Hillman has the perfect way to add a punch of color with a bright bag.
Embrace the ladylike dress code with a calf-length skirt; then give it the coolest kind of finish with just your shades.
Christine Centenera perfected the art of sophisticated seasonal dressing in a sleek skirt, a little sheer, and just the right accessories.
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.
Juxtaposing a little embellishment and leather is the perfect way to ease into the cooler months.
Shiona Turini's laid-back look came with a moto jacket and a knit pencil skirt — certainly worth replicating.
Give your romantic dresses a sharper edge with a black blazer and lace-up flat boots.
Taylor Tomasi Hill knows that there's more than one way to wear a scarf — a valuable lesson to inspire your Fall styling.
This season, get ready for the return of minimalism — crisp black-and-white palettes and easy pieces.
Colorblock trousers in supercontrasting shades are guaranteed to catch the eye.
Easy Autumn days call for easy styling — like a skirt finished with slip-on kicks.
Proof that simple can be simply stunning; just throw your favorite sweater over a slip dress for effortless Fall dressing.
Olivia Palermo perfected the classics in a powder-blue skirt and a button-down.
Take a cue from Sarah Rutson and play it ladylike in shades of navy and black.
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.
Julia Sarr-Jamois helps answer any lingering questions about how to wear sneakers right.