Advertisement
Slideshow will continue in seconds. Click to skip
September 1
Wear the thick, tweed-y skirt that looked out of place in July and August and show off your summer tan with bare legs. Best of both worlds. Click through to shop the look.
September 1
September 2
It's Labor Day. Instead of matching all the other girls in white jeans, wear a black dress—especially a cool cutout one you won't be able to wear much longer. Click through to shop the look.
September 2
September 3
Give a suit a girly spin, whether it's via the color, the pattern or even something as subtle as scalloped details. Click through to shop the look.
September 3
September 4
Punctuate a denim tuxedo with a bright red lip. It's really all it needs. Click through to shop the look.
September 4
September 5
Balance a sharp pencil skirt with a "DGAF" sweatshirt. Click through to shop the look.
September 5
September 6
While it's still warm, break out the pieces that are tricky to navigate with winter layers (delicate beaded things, poofy silhouettes, bold suits that look better on their own, not covered up). Click through to shop the look.
September 6
September 7
Transition your white jeans into fall by swapping your go-to sandals for ankle boots. Click through to shop the look.
September 7
September 8
Leather skirts are an investment, but might be a worthwhile one this year: even in simple cuts and solid colors, they still look so sleek. Click through to shop the look.
September 8
September 9
Get a little more mileage out of those amazing sandals you bought during an end-of-season sale. (Wear 'em even when you don't have an occasion. Why not?) Click through to shop the look.
September 9
September 10
Toss a button-down underneath a beaded top for some creative layering. (If Jenna Lyons does it, it's cool.) Click through to shop the look.
September 10
September 11
 The only topper that packs more punch than a leather moto jacket is a colorblocked leather moto jacket. Click through to shop the look.
September 11
September 12
Pairing a bright and a dark from the same color family (hot pink & burgundy, cobalt & navy) always looks awesome. Plus, it's a good way to wear your summer neons well into fall. Click through to shop the look.
September 12
September 13
Casual jeans, head-turning heels and a fun bag: it's got a ready-for-anything quality we love. Click through to shop the look.
September 13
September 14
Branch out of the nautical stripes you wore all summer and try some other colors instead. (We especially like jewel tones: deep greens, yellows and eggplant purples.) Click through to shop the look.
September 14
September 15
You'd be surprised how many outfits a bag like this can pull together. Click through to shop the look.
September 15
September 16
Ahh, camo jackets, the unofficial cool kid of light fall jackets. If you don't already have one, you need one. Click through to shop the look.
September 16
September 17
Fancy, designer-y sneakers can add the dose of swagger your basic fall outfits were missing last year. Click through to shop the look.
September 17
September 18
For an Almost Famous-y vibe, pair a shearling jacket with bohemian jewelry, then walk out the door with bedhead and big sunglasses. Click through to shop the look.
September 18
September 19
Black or tan ankle boots would've worked here, too, but with leopard ankle boots it's insanely good. Click through to shop the look.
September 19
September 20
Push trendy printed denim into sophisticated territory by adding pointy toe heels and and some classic aviators. Click through to shop the look.
September 20
September 21
Leather vests are less common than leather jackets, and that's cool. But the real kicker is that they're got amazing seemingly endless layering possibilities to them, too. Click through to shop the look.
September 21
September 22
Conservative outfits like these need major shoes to keep them fun and fashion-y, and these metallic sandals do the trick perfectly. Click through to shop the look.
September 22
September 23
Every girl needs an easy, understated camel jacket like this. It's brilliant when you want to wear one of your busiest summer dresses and want something warm—but uncomplicated—on top. Click through to shop the look.
September 23
September 24
Cutoffs and a blazer is one of our favorite casual-polished pairings, like something a celebrity would wear for running errands in West Hollywood. Click through to shop the look.
September 24
September 25
Balance a floaty maxi skirt with a heavy leather jacket. (All the London It girls are doing it.) Click through to shop the look.
September 25
September 26
Because sometimes you want to add a more literal back-to-school vibe to your outfit. Click through to shop the look.
September 26
September 27
Unusually warm days at the end of the month are great opportunities to wear those kicky little mini skirts you'll be sad to store. Click through to shop the look.
September 27
September 28
It might seem like a niche thing, but a coat dress might just be what your wardrobe's really missing. Easy-but-polished, it'd be one of those things that sneaks up on you and you end up wanting to wear everywhere. Click through to shop the look.
September 28
September 29
Use a snakeskin skirt to add some bite to your basics. It's less ubiquitous than a leopard one and tends to look more sophisticated. Click through to shop the look.
September 29
September 30
Paper-thin silk pants + thick moto jacket: not-hot, not-cold-yet dressing at its best. Click through to shop the look.
September 30