30 Days of Outfits to Kick-Start Your September

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.

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

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.

Digging the denim and leather look, always.

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

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

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

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

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.

Take note and let your pants be the statement piece.

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.

All black looks chic, anytime, anywhere.

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.