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STYLIZER
Five Great Bets for Layering This Fall

It's not exactly chilly outside yet, but we still can't help but lust after all the sweaters, coats and tights that are filling store window displays. Though we'll be in bare legs and miniskirts for almost another month, we're having heady daydreams about print mixing and suffocating combinations of shirts under sweaters under jackets under coats that just can't be ignored.

To that end, we present five great bets for fall layering--stuff you can wear alone in the next few months, then pile on when the real cold sets in.

TRENDTASTIC
On the Prowl: Totally Cool Leopard Boots for Fall

Leopard is everywhere this fall, from Current/Elliott's dappled skinnies ($198) to Opening Ceremony's bold navy maxi skirt ($169). But the most lowkey way to rock the trend is flat boots. Rendered in casual silhouettes from desert boots to ankle booties, leopard print is a quirky way to mix prints in your fall weekend look.

A staple for fashionista's weekend looks last fall, the desert boot gets a rad makeover in leopard, by Matiko. Bonus points for the flattering hidden wedge. $118 at Nasty Gal.

SHOP INDIE
Get Bohemian Chic for Fall at Nolita's Poppy Boutique!

Nolita's Poppy Boutique is the store out-of-towners dream of when they come to New York to shop: trendy but classic, hip, but unintimidating, affordably priced, and consistently stocked with pretty garments dabbed with a vintage, boho feel. With autumn just around the corner, the boutique delivers again with fall pieces that'll have you wishing that the chill in the air would hurry up and get here. The bright and airy boutique is already stocked with fall-ready garb like a killer Lauren Moffatt navy cape with oversized leather pockets that give it a decidedly '60s-mod appeal ($385) and a red-and-white striped dolman-sleeved jacket by Myne that has all the sophisticated edge of the hippest '80s lady-who-lunches ($285). They've also got a great selection of comfortably chic Tucker blouses ($250-$285), and adorable tribal-print shorts in fabulous neons ($132) that would look great with tights and riding boots come fall.

THIS JUST IN
Alexa Chung for Madewell Photos Have Us Counting Down the Days

Alexa Chung's line for Madewell last year was the best kind of celebrity and mass retailer collaboration: a series of incredibly wearable masculine-feminine garments that had the gamine it-girl's downtown appeal written all over it. When the line sold out in a snap, we were left wanting more--and luckily, her second season for the store (which, for the unitiated, is something like the Skipper to J. Crew's Barbie) is arriving in late September.

To get us even more amped, Madewell has released a series of dreamy photos of Chung in a few pieces from the line. Her effortless, tomboyish mix of streetwear and designer garb is perfect for autumn, and from the looks of the stills, we can expect preppy separates with a dab of whimsy, like a palm tree-printed blouse, a lace top paired with stone-colored Daisy Dukes, and a miniskirt that's just the right length for an Indian summer. The photos themselves give us more of a hint of the line's mood: they're washed out, Hipstamatic-like prints, snapped around Austin because our gal gets ongoing inspiration from "girls in bands who live their looks,” according to a statement from Madewell. Put September 22nd, when the line appears online and in Madewell stores, on your calendar, because it's sure to sell out faster than any indie band the former MTV VJ is listening to now.

STREET STYLE
Understated Elegance at Escape to New York

If nothing else, summer music festivals are a great guide to dressing hippie-dippie chic. Bonnaroo and Pitchfork are magnets, it seems, for girls wearing tie-dye and flowers in their hair; who else is the market for gorgeous $500+ feather headdresses and those rad Proenza tribal prints?

The Escape to New York Festival on Southampton's Shinnecock Indian Reservation was no exception, with flocks of girls wearing dreamy, statement-making get-ups that seemed made for patronizing trucks serving cuisine from the Fat Radish and gallivanting around the "glamping" (a portmanteau of "glamorous camping") site. But among the more radically attired (there was a woman in a miniskirt made of MetroCards--we kid you not), there were a few ladies in elegantly understated ensembles that nailed the sophisticated festival look.

STREET STYLE
From Desk to Dinner: Sarah's Post-Work Cool

Even when you're already running late to meet friends for post-work drinks, the urge to jet home and change from your business attire into something more comfortable can be irresistable. We spotted Sarah walking into a bar on the East Village, having just completed the post-work change into an outfit that is casual but well put together.

The key to her post-work cool lies in the structure of her otherwise laid-back pieces: the pleats on her leather shorts give her a sense of polish, and she pulls her look together by rolling the sleeves of her denim button-down and tucking in the gray tshirt layered underneath.

The look is pulled together by edgy, strappy sandals and thin gold bangles and toned down with a practical oversized canvas tote.

TRENDTASTIC
Own the Midi Skirt Trend With These Killer Silhouettes

After a seemingly never-ending period of hemlines inching ever-upwards, one of fall's key trends offers the skirt in a length that's more conservative but just as dynamic. The midi skirt, hitting just below the knee or mid-calf, feels decidedly ladylike but somehow modern, and designers are offering a variety of silhouettes to make this look accessible to all.

ASOS offers a number of midi skirts, including this universally flattering Midi Skirt with Pleat Waistband that comes in three colors. With its a-line and high waist, this classically feminine piece priced at an affordable $60 is a great option that can be worn for seasons.

STREET STYLE
A Chic Chinatown Bartender Works a Globally Inspired Look

In a hidden nook of Chinatown sits a romantic little bistro called Les Enfants Terribles, where the waiters are just as much a feast for the eyes as the food is for the stomach. One such gent is French-born Pierre, who not only mixes a mean mojito but also looks tres distingue while doing it. On a recent Tuesday afternoon, he was doing just that in an outfit that speaks to his many travels: a graphic tshirt purchased while he lived in Amsterdam, shorts from his stint in Montreal, a necklace he purchased for his mother in Rome, and the classic American sneaker--Converse Chuck Taylors--from his current place of residence. By rolling his shorts at the cuffs and wearing geeky chic glasses, he adds an edge of sophistication to a perfectly casual look.

STREET STYLE
Street Style: Handsome H.B. Beats the Heat

We spotted H.B. strolling around the Lower East Side on a steamy morning, and were taken with the way this handsome fella put a twist on the polished preppy look. He paired a sky-blue J.Crew button-down with mustard jeans, rolled just-so at the ankle, for a surprisingly pleasant and punchy color combo. Then he finished off his outfit with beautiful white bucks from Johnston & Murphy. His Persol aviators and rad haircut add a bit of edge to his clean-cut look. How he's wearing jeans in this heat beats us--but the guy sure does look handsome!

KILLER DEAL
Killer Deal: Marni Silk-Satin Dress is 65% Off

Holy discount! This Marni Silk-Satin Dress in a pretty pink hue has a flattering drop waist and just a bit of swing to keep it breezy for summer. But the chicest thing about it is that it’s marked down from $775 to $271—that’s 65% off! Available at TheOutnet.com.