In much the same way that I likely drive my poor younger (and cooler) sister crazy with nagging questions about who the new “It” Brooklyn band is, the most over-repeated question I get is: “Who’s the next hot designer?”

Fortunately, once a year, a well-respected panel figures that out for us (and for the Vogue/Fashion Fund Finalists). In the past five years, top brass like Proenza Schouler, Phillip Lim, and Rodarte have been among the designers hand-picked to be finalists; this year, the nominees are a varied mix of sexy red carpet dress-makers and punky jewelry designers. Using this handy guide, you too can act like the insider’s insider.

The Red Carpet Favorites
The darlings of any award finalists crew, these designers would be considered the next Valentinos and Balenciagas of the world… if they weren’t clothing A-list celebrities already. Prabal Gurung is likely the best known of the group, since his flattering, feminine dresses have already graced the likes of Michelle Obama and Demi Moore. Christian Cota, on the other hand, is one rung below (dressing Gossip Girls and small-screen lovelies like Rose Byrne) though no less talented. Then there’s Joseph Altuzarra, the boyishly charming talent known to few in middle America, but absurdly beloved by editors and insiders (aka “the deciders”) for his perfect tailoring and latter-day Tom Ford for Gucci vibe.

The Street Locals
The two most notably street-inspired designers actually both specialize in jewelry. While the majority of the womenswear talents have a fairly polished aesthetic, Eddie Borgo and Pamela Love hew closely to the punky reality of downtown and Brooklyn. Eddie Borgo even got It-girl (and Elle staffer) Kate Lanphear to star in the latest ads for his chunky, spiked pieces. Love, on the other hand, is a note-worthy fixture in Williamsburg (she drums for a band called Scorpio Rising), in addition to designing moody, talismanic pieces like heart-with-flame pendants and armor-like cuffs.

The Menfolk
Note to the gents out there: Menswear is back. Men are increasingly aware of how they’re styling themselves, and that’s reflected in their buying habits. (The new metrosexual is the nouveau-hipster? We’re still puzzling, but it involves fitted check shirts, glasses, and well-tailored suiting.) Among those highlighted by the Fund this year are southern gentleman Billy Reid, the downtown-crisp collections of Loden Dager, and high-styled looks of Robert Geller.

The Wild Cards
In any group of upstart finalists, there should be the folks with whom even the fashion editors are a bit less familiar. Los Angeles-based Gregory Parkinson’s collections boast some seriously original prints, giving the reigning louche SoCal aesthetic an exciting, ladylike update. On the opposite end of the spectrum, Moss Lipow is an interesting name to add to the mix, since he’s a statement eyewear designer (one might recognize his Aviator and Black Hornet styles).

On a recent afternoon in late July, as the temperatures pressed upwards of 98 degrees, I passed Saks Fifth Avenue and did a double-take: There, in the window, was a new fall look that, while stunning, included a hip-length fur vest. Fur. In July.

It’s long been one of the great mysteries of retail that you can rarely find the things you need when you actually need them: It’s impossible to find a decent swimsuit for Fourth of July weekend; and come winter’s chills post-Thanksgiving, you’re lucky to find a well-fitting winter coat while jostling for position with hordes of holiday shoppers in the sale section.

While the fashion industry continually struggles to infuse the retail market with an ever-rotating supply of new clothing—creating more and more “seasons” like Pre-Fall and Resort to dazzle American shoppers who, it seems, never really stop shopping—the one area where they continually fall short is in timeliness. The main competition, of course, comes in the form of cheap-manufacturing, fast-fashion outlets like Forever 21 and H&M, which can afford to turn merchandise week-to-week. Meanwhile, top designers remain bound by the fashion calendar to garner the most publicity for a new collection at the September fashion week shows, where, of course, they’re not even showing fall wares (they’ll be showing spring 2011). This September, the powers that be are organizing several events to counter-balance that confusion, from Fashion’s Night Out (a Friday night during Fashion Week where stores host events and stay open late to encourage shoppers) to a massive fashion show at Lincoln Center, just before Fashion Week kicks off, where designers will show current season pieces only.

Though, in reality, these are strange tidings indeed: most insiders see these idiosyncrasies as merely a way of life, and buy accordingly—as should you. In the interest of keeping us all well-heeled for the upcoming season, here are a few staples to consider investing in now, so that you don’t miss them once you can actually, oh, imagine putting on a pair of socks without sweltering.

A Shearling Jacket
This season, several fashion houses caught the Amelia Earhart bug, creating tough-yet-trim aviator jackets fully lined in shearling. (Remember, though, “shearling” isn’t shorn wool, it’s the skin of the lamb with the wool attached, so be mindful of PETA.)

The Pair of Boots You’ll
Wear All Fall
You’ve probably already seen them in the window of your favorite store, or in an email blast you got last week. Maybe they’re laceups, maybe they’re brogues, maybe they’re clogs—odds are, if you’re obsessed with them, you’re not the only one.

A Heavy Swing Skirt
Good old-fashioned 50s femininity made a big comeback this season—both in moody schoolgirl kilts (think Buffy over Britney) and circle skirts rendered in heavy wool and even leather. Imitations will run rampant come October/November, but the high-quality originals will vanish by time Fashion Week hits.

A constant state of turnover is more or less status quo for the city’s retail scene, but the trials of the recession really seem to have brought certain indie boutique-heavy areas (the Lower East Side and Nolita in Manhattan, for example) to their knees. In some cases, the result has been blocks packed with empty storefronts, but in others, a few key new entries into a neighborhood is paving the way for mainstream retail to gain a serious foothold.

Such appears to be the case on Atlantic Avenue, where news that Manhattan’s prince of luxury retail, Barneys, announced plans to open a Co-op outpost near Trader Joe’s this fall set off quite a shopping-focused fever.

Suddenly,The New York Times was reporting that a number of other “high-end retailersâ€� had been scouting in the area, including Swarovski Crystal and Anthropologie. There may already be an Urban Outfitters in the ‘hood, but it’s clear that it took the buy-in of a national luxury brand to open the floodgates to that level of big-name branding. The main question, of course, is as the shopping potential for the area ramps up, will some of the more beloved indie shops (or restaurants, for that matter) be able to hold on?

A tough 2009 has certainly brought more than a few storefronts on the market for big retail to choose from. Just this month, designer Jodi Arnold confirmed that she’d be taking over an old restaurant space at 347 Atlantic, bringing her signature ladylike dresses to the block. Arnold’s actually a Brooklyn resident, so the move makes sense, but the fact that designer’s first brick-and-mortar store is on University Place in Manhattan should give anyone a good idea of the brand’s identity. Arnold may not be a household name, per se, but in terms of fashion, she’s not exactly known for being on the fringes, either. Stylish, but not avant-garde. Bottom line, it’s worth noting that the talent the thoroughfare is now attracting isn’t undiscovered, forward-thinking designers—it’s savvy folk who’ve likely already engaged in a collaboration with, say, the Limited (as Arnold has).

It’s hard to complain about a successful retail boost in a pulsing nerve center of Brooklyn, but no doubt the local indies are about to feel the heat of an ever more developed playpen. Smith Street may be home to editor-favorite stores like Bird, Epaulet, and Dear Fieldbinder, but some of the neighborhood’s strongest indie shopping destinations are currently clustered along Atlantic, from Hollander & Lexer to Butter by Eva Gentry and Mafalda vintage. Here’s hoping the latest influx along the route only serves to strengthen them all.

The recent cult fandom surrounding the flea market is really the product of a perfect confluence of trends: a young peoples’ lust for Old New York and community, the resurgence of vintage, food-truck mania, and the recession. The flea plays to a generation nostalgic for the alt-weeklies and swap-consignment shops of the 90s, while also providing an excuse for the brunch-and-sip crowd to venture outdoors and still fulfill its social requirements.

Brooklyn Flea
Saturdays at 176 Lafayette Avenue, Sundays at One Hanson Place; 10-5.
The Brooklyn Flea may not have started the movement, but it’s become the poster child, from a Martha Stewart cameo to a New Yorker writeup. And yes, it lives up to the hype. The curated flea offers 100-plus vendors#&8212;from hodgepodge antiques and Dulcinee vintage to Claudia Pearson-illustrated calendars and Lillian Crowe jewelry#&8212;as well as a mouth-watering array of food including oven-fired pizza and lobster rolls from the Red Hook Lobster Pound. This year the Flea added a new location to its roster: the luminous old Williamsburg Savings Bank at One Hanson, where vendors fill old teller windows and visitors gaze up at the mosaics and wrought-iron screens.

Hester Street Fair
Saturdays and Sundays at Hester and Essex Streets; 10-6.
Once home to one of the city’s oldest pushcart markets, Hester Street Fair has enjoyed a revival this summer thanks in part to charming MTV correspondent SuChin Pak and a group called The Big Social: architect Ron Castellano, digital wiz Adam Zeller, and Pak’s brother, Suhyun. In a few short weeks, the smaller, equally curated market has become Manhattan’s stylish set’s answer to the Brooklyn Flea, with its own brand of slick vendors#&8212;vintage from Wanderlust and jewelry from Erica Weiner#&8212;and its own lobster rolls, courtesy of Luke’s. If the “stylist tent” is in effect, make the trip: One weekend, there was vintage Betsey Johnson and Gaultier.

Artists and Fleas
Saturdays and Sundays at 129 North 6th Street; 12-8.
While the Brooklyn and Hester markets make nods at history, Artists and Fleas gets props for actually being one of the older of the “new breed” of flea. First opened in 2003, Artist and Fleas transforms an empty warehouse on North 6th Street every weekend into a vibrant shopping destination featuring quirky vintage, punky Astali jewelry, and one-of-a-kind clothing pieces from A Strange Truth. The market may not have the street cart bonus that others have, but Bedford’s nearby restaurants provide more than worthy competition for a weekend outing.

If the toys that occupied one’s youth are any indication of future careers, it makes sense that my favorite doll growing up was Day-to-Night Barbie. For those unfamiliar with this particular Barbie iteration, the doll featured a daytime wardrobe (a pink and white cream suit!) that reversed into a cocktail dress. True story. Nowadays, the doll comes to mind in those moments where an after-work cocktail party requires a pivotal uptick in one’s ensemble between the hours of 6:30 and 8pm-a tricky proposition when one lives in Brooklyn and works in Manhattan. In lieu of reversible pencil skirts, however, a truly killer statement necklace will do quite nicely.

Whether the new breed of eye-catching necklaces has its origins in recession-inspired dressing (throw grandma’s old necklace over that t-shirt!), J.Crew’s now ubiquitous madcap styling (layer 16 necklaces and pair it with contrasting patterns!), or the proliferation of vintage boutiques and curated flea markets, more and more one sees a cornucopia of glittering, colorful neckwear on the streets. And in fact, they do make for the perfect day-to-night piece: A simple ensemble, spiced up with a truly dazzling necklace, is instant evening. Now for the good news: Many of the indie jewelry designers you know and love have gone mass market for summer.

Lizzie Fortunato (a line formed by two sisters) jewelry is most often found at worthy indie spots like Stuart & Wright in Fort Greene, and boasts a crafty-meets-sophisticated appeal-think patchwork fabric and gold beading. Alas, one often pays for said originality (pieces can run between $400-$975), so news that the sisters were creating an exclusive, affordable line for J.Crew spin-off Madewell is excellent, indeed. A dazzling “bouquet” necklace with flowers made out of pinwheel-like fabric is $118, while a beads-and-chains offering is $62.

Another well-regarded label, Fenton-Fallon, has also partnered with J.Crew: In this case, Dana Lorenz (recently nominated for a CFDA award) created a special line for the chain that really distilled her antique-looking, all-out glam aesthetic into a series of pieces including a necklace dripping with ropey chains for $195, and a massive choker with huge crystals and bows for $295.

Last, but not least, blogging duo Kristin Reiter and Valerie Killeen of BleachBlack may have quirky taste on their conversational style site, but they have truly perfected the costume-looking necklace with their limited-edition rhinestone piece for Urban Outfitters-available for a mere $38. Go on, wear it over a t-shirt and see if anyone accuses you of being under-dressed.

We’ve officially cleared Memorial Day, had our first day of good-god-how-does-one-even-wear-clothes-in-this-heat, and safely entered the land of linen pants and white dresses. (This writer has even had her first sweltering night with the AC busted—a true harbinger of the city’s long summer nights to come.) While spring and fall may have weeks of runway collections devoted to them, make no mistake: Summer is its own season. Here’s what to wear.

Horizontal Striped Shirts
There exist, in the fashion world (and sometimes outside of it), people who really do create little collage mood boards for each season and stick to its overall theme religiously, creating spin-off ensembles of “St. Tropez casual” or “safari prepster” or what-have-you. Whether or not you know you’re in the middle of a “French nautical” moment, you should know: A striped shirt is this year’s white V-neck. If you’re smart, you buy more than one—perhaps one slouchy tank, one Parisian-inspired long-sleeve style with a boat neck collar.

Jean Cut-Offs
A nod to summer’s music festival season (with a dash of west coast nostalgia), this summer’s iterations are higher-cut and seriously short for girls (paired with an unexpectedly formal silk shirt, perhaps), and faded and worn for gents, cut off a couple inches above the knee.

Eye-catching Printed Dresses
The prints, prints, and more prints theme has made a strong transition from spring to summer, with florals, of course, becoming the most pervasive frontrunner, running the gamut from delicate Liberty-inspired flowers to big, brassy watercolor patterns. If a little floral vintage-y dress seems a bit too prissy for you, give the season’s sporty, surfer-inspired tie-dyes a spin (take Proenza Schouler’s spring 2010 collection as a jump-off), or else something a bit more graphic and tribal. We’d suggest looking into up-and-coming label Suno, which takes many of its prints from Kenyan kangas.

Wooden-sole shoes
Ok, so yes, it’s true, clogs are a huge trend right now. It started on the spring runway of none other than Chanel, if you can believe it. No. 6 (a great boutique on Centre Street) has a brilliantly versatile clog (that you can actually customize in different fabrics), or you can go for the closest thing to the original from Swedish Hasbeens at Kaight on the LES. If you’re clog-averse (and who could blame you), you can play halfsies with the trend by incorporating a wooden sole into your footwear—from Rachel Comey’s tied-up-and-tasseled platforms (they’re comfy, I swear) to Belle by Sigerson Morrison’s simple wooden-soled sandals.

Pants: Silk, Tap, and Pegleg
Pants are back! Sure, when it’s 100 degrees out, covering one’s entire leg doesn’t seem like the most tantalizing notion, but a pair of navy silk pants that tapers toward the ankle is surprisingly lightweight and breezy, and rolled-up trousers telegraph summer picnic like few other things. The most curious trend of this season, however, has got to be tap pants: little flimsy silk shorts that seem better suited to a retro lingerie photo shoot than a trip to the Brooklyn Flea. Yet, somehow, these have morphed into rather charming silk shorts with scalloped edges and fitted waists. Not always flattering (to be perfectly candid, I look ridiculous in them), but when worn right, rather dashing.

The recent rash of menswear-inspired clothing for women has created a surprising envy moment among women who live with their mates. While the old days may have involved excess cooing over (and, just as often stealing of) old, perfectly worn concert tees of boyfriends past and current, the latest evolution is a full-on assault on all manner of items in a man’s closet: crisp striped button-downs, worn denim, oversize cashmere sweaters, and more.

While, it’s true, I covet no small portion of my better half’s wares (there’s a perfectly preppy raincoat I still have my eyes on), what has most transfixed me, oddly enough, have been his bags. They’re rugged, perfectly worn, and just oversize enough to suit my pack-it-all-in-one-satchel-for-the-weekend purposes. Plus, there’s something about a man’s bag that has such a sense of authority, in ways the bags geared toward women—with their quilted cotton and too-girly or graphic prints—just don’t. Alas, unlike the worn tee I used to be able to steal without him noticing for a few weeks, these bags have proven rather difficult to sneak out of the house. Fortunately, the market has risen to meet the demand, and there are more than a few brilliant stand-ins to satisfy the travel needs of Memorial Day Weekend and beyond.

For those craving an outdoorsy bag that’s still chic enough to bring to the Vineyard, Filson is still really the ultimate classic hunting-inspired silhouette. The Sportsman’s Bag is more than sufficient for weekend travel, and might even fit under a plane or train seat if you pack right. Perhaps best of all, you don’t have to venture into a faux-outdoorsy section of a department store to get one; you can hit up the real thing at Paragon Sports.

If the whole rugged look suits your purposes, take it one step further and snap up an authentic Klein Tool Bag at Home Depot. Honestly, I never imagined a tool bag could look chic—outfitted in crisp white canvas and jaunty leather buckles, it’ll look even better once it gets a little roughed up, and at $60 for a 20-inch version it’s a steal. Just picture either rough-and-tumble bag paired with a feminine floral dress or a crisp white button-down and dark jeans and you start to get the idea.

In addition to masculine cargo bags, a more schoolboy-inspired trend has been making a return: backpacks. Once the realm of earnest middle schoolers, backpacks have become the fixation of more than a few It-designers, and stores like Opening Ceremony are now stocking myriad classic iterations from Swedish-based Fjallraven (the company that practically started a backpack movement in the 70s)—each just $60. For something a touch more high fashion, grab one of Rachel Comey‘s hiking-inspired backpacks: In classic Comey style, each bears an eye-catching original print—from watercolor blue to graphic forest green—in either a leather flap or traditional zip-up style. Between the duffels and the satchels, you’ll have room enough for your clothing and your summer reading essentials.

It must have seemed like a horseman of the apocalypse to the stylish denizens of Soho: Crocs signage on one of the area’s charming, historic buildings, at the corner of Spring Street and Wooster. But don’t let a new Crocs outpost in the neighborhood blind you to the groundswell in the city: Ever so slowly, real, honest-to-goodness fashion is creeping back into previously big box-dominated areas like Soho and Bleecker Street.

Sure, there’s still an unavoidable sickly-sweet cologne wafting from Hollister on Broadway, and some revered indie shops like Lyell can’t afford to stay afloat (Lyell has announced it will shutter in June), but there are worthy openings ahead. Isabel Marant’s much-hyped new store on Broome Street—feted by no small number of seriously chic editors—brought a new focus to an area previously dominated by stores like Sephora and Armani. Marant’s husband Jerome Dreyfuss‘s handbags next door are, similarly, evidence of more interesting fare in the neighborhood, and Aussie It-label Zimmermann has also just opened on Greene Street.

On tap for Soho launches this summer and fall: a new, concept-driven Diane von Furstenberg store that will include both the label’s contemporary collection and vintage pieces come July; and a Ralph Lauren space to fill the void (if one can call it that) left by the less-than-savory denim store Replay on Prince and Greene by fall. Granted, DVF and Ralph Lauren are far more big-box than Rachel Comey, but they’re both eminently more desirable neighbors to have than, say, that terrible Parasuco brand that moved its club tops and jeans into the respectable East River Savings Bank. (Parasuco has, incidentally, recently shuttered. More good news!)

Even Bleecker Street, the stretch of turf bookended by Reiss, a UK chain, and eighteen bajillion Marc Jacobs stores, has gotten an uptick in its roster. Freemans, an LES shop with its origins in the popular restaurant of the same name, recently opened a Bleecker Street offshoot near Christopher, boasting an in-house suiting label and Quoddy boat shoes. Better yet, APC has announced it will open a new location on the block, building on the success of its Soho store.

Sometimes it’s easy to forget how quickly a place can transform in New York. Heck, when I moved here, everyone was wearing trucker hats and trying to get into Bungalow 8. The city can recover from its own mistakes—and no, this doesn’t mean that Hollister will be closing anytime soon, nor does it mean that Soho is suddenly going to be the home of poor, hip artists again, but it’s a start.

Everyone knows that once a girl turns into a soon-to-be-bride, she starts to believe the known universe revolves around the wedding. Thusly, as a soon-to-be-wedded person myself, I wasn’t surprised that I started noticing a plethora of wedding-related fashion news—new stores, new websites, new lines. However, I’m slowly discovering that it’s not just me—the industry itself is transforming.

The new energy in the bridal market stems from a really basic issue: More and more brides have started opting for off-the-rack dresses over customized gowns. Take me, for example: Firstly, conventional wisdom dictates that I should allot up to six months’ time for a customized designer dress—be it from Kleinfeld or Vera Wang—and for good reason. These stores are tackling special requests (“take the sleeves off,” “fix the bustle”) from countless brides each season, and are dealing with complex gowns—corseting, lace, layers of tulle, the mind reels. However, we’re aiming to get hitched in less than six months, which already puts me out of the running for “the dream dress” among many circles. Secondly, I may be a fashion editor with certain connections, but even so, designer dresses (especially custom ones) are incredibly expensive, and in this day and age, even a shopper-for-sport like myself starts to draw the line somewhere.

And so, a doorway has opened for a new kind of bridal market, that’s really (let’s face it) been spearheaded by J.Crew. J.Crew first introduced its bridal collection in 2005, and in the five years since, has ushered in a wave of less-expensive, off-the-rack bridal offerings. In fact, its brand of one-stop-shopping wedding retail has been so successful, J.Crew is opening a stand-alone wedding salon on the Upper East Side in late spring, mere blocks from Vera Wang herself. As further proof of the triumph of mass-market over custom, Wang has even announced a recent partnership with… wait for it… mall retailer David’s Bridal on a lower-price line of dresses. David’s Bridal. Let that one sink in.

In the e-commerce space, Net-a-Porter has launched its own bridal boutique, angling itself pretty much in direct competition to J.Crew by offering upscale (yet still off-the-rack) dresses from insider-favored lines like Lanvin and Rick Owens, with Louboutins to match. Urban—the company behind Urban Outfitters and Anthropologie—has also announced plans to launch a wedding line, and even Ann Taylor has introduced a strapless, tiered wedding gown for $495.

Alas, for a gal like me, who’s looking for something more personalized and “special” than, say, an Ann Taylor dress, but is also not willing to sign on for a six-month custom piece that she doesn’t even get a hand in creating, the options may have become far more varied, but they’re not necessarily more satisfying.

Almost exactly four years ago, I went to surf camp in Costa Rica. At the time, I was far from what anyone would call athletic (frankly, that hasn’t changed), but what scared me more than falling, limbs flailing, off my board was actually looking the part of the amateur I was. At worst, I thought, I would show up on the beach looking kick-ass and then proceed to fall off my board, repeatedly. Unfortunately for me, that proved harder than I thought. Greeted with an onslaught of hearts-and-butterflies-bedecked “rash guards for chicks” or, alternatively, board shorts that could have been cut for men, I was so frustrated I actually described the style vacuum in detail for this magazine. So, needless to say, the proliferation of surfer-inspired (as well as actual surfer) gear in the spring collections has been seriously exciting.

If something’s going to catch on, you usually know right away. In the case of the spring collections, the whole sporty-girl-meets-surfer trend started cropping up within days of Fashion Week’s end last September, with girls on the street attempting the side-braids from Alexander Wang’s runway show and starlets-of-the-instant like Kristen Stewart sporting Proenza Schouler’s eye-catching tropical tie-dye ensembles. Jack McCollough and Lazaro Hernandez (the designers behind Proenza Schouler) really managed to tap into something vital with their colorful pieces for spring, something that everyone quickly latched onto, from reef fish-inspired dresses to wetsuit-ish long-sleeve tees—all with a beachy, tropical flair that erred strongly on the side of sporty rather than resort. Though that one collection may have represented the trend at its most intense, the reverberations seemed to be everywhere, from Diane von Furstenberg’s tie-dye print dresses to BCBG’s bodycon mini, which started to look like a new kind of mini-wetsuit.

Now, with spring in full bloom, there seems to be more surf-related gear, even for those who don’t have a share in Montauk. Cynthia Rowley, a veteran of the sport, has put together a collection that ranges from sunny California graphic tees to actual, honest-to-goodness wetsuits in pastel color-block. To further establish the collab’s cred, Rowley even made a surfboard with forward-thinking designer Thomas Meyerhoffer. Browsing the collection at Barneys (it’s also available through Roxy), I couldn’t help thinking a neoprene minidress paired with metallic flats would look pitch-perfect for a warm night’s cocktail party. Who knows if we’re bringing surf camp to the city or the city to surf camp—either way, whenever I head back to Costa Rica, I’ll have more to pack.