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The impulse when picking a tricky dress with multiple elements like Kerry's Jonathan Simkhai number might be to play it safe with the extras. But as she shoes in her leather-trimmed suede jacket, polka-dot Salvatore Ferragamo heels and crown braids, somteimes, more is more.
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A simple striped sweater and denim skirt (like, say, one of these 15 we picked out for you) can be interpreted so many different ways – but it's Alexa's '70s-in-London version (thanks to her lace-up boots and ultra-luxe Gucci suede trench) that's speaking to us right now.
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A sundress and a denim jacket is pretty much the No. 1 reason we can't wait for spring to get here, and now we have a No. 2 reason: The opportunity to match the monogramming on our Madewell jackets to our too-cute shoulder bag (like her Max Mara style).
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Your go-to outfit formula this spring: Find perfect white dress. Add complementary bright accessories. Repeat. (Our favorite element of Rebel's look: How cute her A-line dress looks with flats.)
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Every star with an athleisure line swears you can wear sweats to brunch, but we needed them to demonstrate this concept. Enter Jenna's casual-but-chic jogger/oversized cardi combo, which gets extra points for the monochromatic accessories.
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Not sure how to style your True Brown K Kylie Lip Kit? Lily goes for contrast by pairing the subdued shade with an explosion of color via her bright bomber, egg yolk-yellow bag and white heels. (And since it's a lot of look, keep jewelry, like her Established Jewelry necklace, to a minimum.)
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If you're going to wear high-waisted white pants, you might as well go all-in on the nautical theme, especially when you do it as crisply as Garcelle does in her waist-tied striped top and brass-button red blazer.
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If played too straight, a Victorian-collar lace top and matching midi skirt (both H&M Conscious Exclusive) could be over-the-top prissy. But a beat-up moto jacket, chunky Brian Atwood platforms and funky Smoke x Mirrors shades help keep the vibe on the “flirty and fun” side of feminine.
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Yes, the outfit's a little basic. But there's a reason why this outfit is such a classic: It looks amazing on anyone and benefits from slight variations (see how Allison's pink lipgloss, mussed half updo and ballet flats give it a French-girl-in-the-'60s vibe?).
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For a polished, professional look, you can't do better than this updated take on a Jackie O. coat-and-dress set: A Tory Burch blanket coat with colors that speak to the coordinating leather mini, with a little mix-and-match interest via the studded top and two-tone block-heel L.K. Bennett Mary Janes.
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A great shirtdress with some visual interest (like the full sleeves and patterned panels of her Chanel number) is the ultimate desk-to-dinner piece – it is great buttoned up with pumps, or with sandals and a lower neckline. And in Kirsten's case, accessories make the outfit: This look is all about that burgundy purse (pulling out one of the flecks of color in the skirt) and classic sunglasses.
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Having a hard time envisioning what to wear your velvet heels with now that spring is here? How about a sheath in the same color family?
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For every one of the sixty million showers (baby and/or wedding) you've got scheduled this spring, Kristin Cavallari's Blaque Label dress, white pumps and pretty cheerleader pony are here for you.
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The Big Fat Greek Wedding star shows just how easy print mixing can be by choosing a two-tone color palette and leaning more on textures than actual prints for contrast.
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The quickest way to make a pair of shredded denim (like Eva's Black Orchid pair) effortlessly chic? Add a pressed white blouse, nude heels and a matte red lip.
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If the phrase “long camel cardigan” immediately conjures up images of retirement communities, let Rosie's outfit banish that from your mind. Her ThePerfext cashmere “coatigan” is a perfectly luxe counterpoint to her low key Paige jeans and gray tee, and she further ups the glam factor with a pair of Elisabeth Bell diamond earrings and a Mansur Gavriel bag.
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Often, “Love Her Outfit” is an ode to the moto jacket, but Ashley's proving why the varsity jacket is quickly becoming the hot topper of choice. Carelessly cuffed boyfriend jeans, aviator-inspired Westward/Leaning shades, white-soled sneaks and – oh yeah – a gorgeous, pricey Givenchy bag, all add to the studied “oh, this old thing?” vibe the jacket gives off.
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TRACEE ELLIS ROSS
For those of you dying to break out your spring clothes, we’re sorry to add to the temptation. But Tracee’s oh-so-feminine dress, with its full sleeves, gathered neckline and ruffled hemline, perfectly paired with nude Soebedar heels and a pink lip, was just too pretty to resist.
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And if you really refuse to wait for one more degree increase in temperature to get into your warm-weather clothes, do as Molly does and top a romantic floral maxi with a fitted leather moto and keep your shoes dark too.
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An oversized blazer similar to Olivia's coat also lends a cool-girl vibe (and some much-needed heat) to a flowy A.L.C. sundress. Earrings in a contrasting shade add to the fun factor.
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In tricky transitional weather, a moto jacket with a shearling collar, like Sophia’s The Arrivals topper, is a cool (and warm) touch for the car-to-event walk, and is easily left on a chair when you're ready to hit the dance floor.
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Thought there was no way to make an exposed-zip denim skirt look chic? Please allow Selena's crisp white shirt, patchwork bag and snakeskin booties (all Louis Vuitton) to demonstrate otherwise.
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An orange dress (Lily's is Victoria Beckham) is tricky enough on its own, but Lily gets advanced style points – and nails the whole outfit – by adding turquoise Gianvito Rossi shoes from the opposite side of the color wheel. A killer neutral coat, by Sally LaPointe, is an elegant final touch. Try a scarlet dress with emerald earrings or a yellow blouse and purple skirt if you're looking for a similarly opposites-attract pairing.
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How do you make black leather leggings and a crop top less “Sandy from Grease?” Try an oversize structured safari jacket (hers is Versace) and bold statement bag (like Gigi's marigold stunner) and add aviators to the whole thing. Voilá: Instant
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You associate J.Lo with all things short, tight and abs-baring, but she proves she can do the Audrey Hepburn thing pretty well too, wearing a luxe turtleneck and cigarette pants with Christian Louboutin shoes and bag, pearls and a just-right red lip.
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Sometimes, a statement coat is all you need to make an outfit, and Jessica's military-inspired brass-button topper certainly qualifies. (Crisp black accessories, a simple Feel the Piece sweater and a perfectly-cuffed pair of jeans make an ideal base for such a cool piece, though.)
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Leather leggings don’t always have to be the most badass item in your closet. They can also meet that “comfy-yet-cool” travel criteria you’re searching for, especially when worn with a cozy, robe-like coat and so-soft blouse.
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And taking Rosie's travel outfit from relaxed to runway-ready? Sexy suede boots, a structured bag and (again) a killer coat – hers is a ThePerfext cardigan.
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Fringe and floral are two of the things we’re most excited to wear this spring, and we’re especially loving the way Kate has combined them, teaming a prairie-print Ulla Johnson midi dress with western-inspired Christian Louboutin boots.
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The model shows exactly what we mean by “mix flirty with edgy” in this Brock Collection ensemble, which she balances with delicate pieces including Stuart Weitzman heels and Anita Ko jewels.
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Tailored, polished, office-ready neutrals get a fun weekend vibe when teamed with cap-toe flats and a bold red bag.
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Hollywood starlets determined to ignore the temperatures are all trying this same trick: Wearing whatever they want (in Hilary’s case, a Zimmermann sundress with strappy nude Bionda Castana heels) and then draping a duster coat over it all.
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Just add tights to Alison’s textured mini and black pointy-toe heels (all Tory Burch) and you’ve got the perfect desk-to-dinner outfit for this Friday night.
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When you're carrying an oversize pearl clutch as your everyday bag, all your basics need to step up their game, which is exactly what Blake does in a embroidered topper, coated black skinnies and shiny leather boots.
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Leave it to the style star to give 2002 style pants a totally 2016 makeover with her fitted blazer (featuring a gold racer stripe accent) and chic black turtleneck (all Tommy Hilfiger).
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The model makes her rocker aesthetic (seen here in her super-skinny pant, lace-up Schutz boots and aviator glasses) season-appropriate thanks to the fuzzy finish on her moto-style Storets jacket.
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With a skirt so bold and attention-grabbing, there's no need to go big on top. Just pair it with a standard black turtleneck (hers is a Wolford bodysuit), classic Paul Andrew pumps and a ladylike handbag (like this Mark Cross silver box).
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If anyone can rock a ’70s-inspired look that includes Joie bell bottoms, a long mustard Topshop corduroy coat (worn over a print shirt, also Topshop), Sunday Somewhere sunglasses and a fringe bag look cool, it's Miss Penny Lane herself.
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The best way to brighten a monochromatic outfit like Hilary's cozy sweater dress, long wool coat, black knee-high boots and bucket bag? With a bold pink pout, of course.
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Rosie's look teaches an important less in Supermodel Style 101: A white button-up and blue jeans make the perfect canvas for bold accessories, which is why she's doubling up on her sartorial impact with her graphic handbag and fire engine red booties.
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You don't necessarily think “boho chic” when you think “Reese Witherspoon,” but the star is totally pulling it off with her coordinated booties and fedora, teamed with a an Erickson Beamon for Draper James statement necklace (though she can't help but bring a dash of her preppy vibe via her sweater/button-up combo).
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How does Jamie Chung make a $15 Cotton On tank look like a million bucks? By pairing it with luxe pieces like a suede jacket and leather pants.
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Dating a rocker has given the supermodel license to experiment with her Coachella side, which she shows off in a floral wrap dress, thigh-high boots and a breezy suede trench.
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How do you add interest to an all-black look, like Kate’s T-shirt dress and Stuart Weitzman boots combo? A belt bag is one way to do it!
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Winter white done right! Emma’s Maiyet minidress, matching heels, cream Behno overcoat and Vita Fede jewelry all feel seasonally appropriate thanks to the scattering of sequins, luxe textures and warm red lip.
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Pops of red (on her lips and polka-dotted A.L.C. blouse) tie together (and sweeten up) an allover leather look like Alison’s, which includes a Tory Burch bag and Jimmy Choo heels.
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It takes a lot of guts to pull of PJ-inspired evening wear, but Whitney somehow manages by opting for an über-polished hair and makeup look (this is not the outfit to wear with sexy, unbrushed bedhead), deliberate accessories (a Devi Kroell clutch and Parade earrings) and strategic skin-showing via her strappy sandals and plunging neckline.
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It’s tempting to wear a cozy sweater like her Tory Burch pullover with leggings and cozy sneakers. But Selena shows how the same sweater can get a dressy upgrade when worn with booties, a moto jacket and a red lip (neck scarf sassy, but optional).
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And here’s an example of when contrasting prints are the way to go. A floral and stripe is the ultimate cool-girl mix, and Jessica’s succeeds thanks to the difference in print scale plus the unifying black throughout. (Silver Brian Atwood heels are bold, but a black pointy pump would work just as well.)
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One look at Riley should convince you that army green should be added to your neutrals rotation – it looks great in a monochromatic ensemble like her Sandro sweater and matching peacoat, and mixes gorgeously with both rich tan (her mini bag) and black (like her Wolford tights and booties).
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Sometimes this gallery feels like it can be called “moto jackets go with everything,” and Lily proves that point here: Not much can temper wide-legged vertical stripe culottes, but a perfectly-cropped topper makes them look effortlessly awesome.
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White jeans in the winter? A total do, especially when worn with a true statement scarf like Olivia’s.
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How do you make a gold lamé jacket low-key? By teaming it with cuffed pants, a distressed tee and layers of necklaces for a look that could easily go day-to-night (and yes, we just said that about gold lamé).
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Sick to death of all your denim? Try a paperbag-waist trouser cut, like Julianne's Maje pair, the surprising cut of which freshenes up her timeless Paule Ka jacket, Elizabeth and James cat-eye shades and white tee.
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The mark of a truly perfect winter coat? It looks as gorgeous with a creamy ribbed turtleneck and winter boots as it does with an evening gown. (Gwyneth's is Michael Kors Collection, if you're feeling splurge-y.)
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Bust out your favorite T-shirt dress from summer: With a shearling jacket, cozy flat suede boots and touches of wintry colors (like her olive bag and burgundy nails), it proves to be a true all-season piece.
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Olivia’s look starts at “schoolgirl chic” thanks to the plaid dress layered over a black turtleneck. Then she kicks it up to “siren” thanks to the patent accessories, mirrored shades and scarlet clutch – all by Dior.
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Maude's wearing her Rebecca Minkoff marled sweater, contrasting turquoise Jennifer Meyer hoops, Blundstone boots and front-button denim skirt to Sundance, but you can cop her après-ski vibes anywhere from work to brunch.
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A gilded, pleated skirt doesn't have to be for holiday parties only. Bella teams hers with an understated blouse and oxblood Tamara Mellon pumps, then belts the whole thing, for a polished look that's perfect for daytime.
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Vanessa boldly wears her J Brand flares with open-toe shoes, but you can copy her whole head-to-toe classic look and stay warm by swapping in almond-toe, chunky-heel boots.
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The power of outerwear is strong with this one, as she further proves in this ivory-buttoned Tory Burch peacoat which looks ridiculously downtown-chic when teamed with cuffed skinnies, Adidas high-tops and a backpack. The perfect finishing touch: a swipe of fuchsia lipstick.
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Just when you thought there was no possible way to put a new spin on the classic button-up and jeans, along comes Katie Holmes in her leather shirt and bow-topped pumps.
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It doesn’t get much easier – or much sexier – than leather leggings, a white top, barely-there sandals and a breezy trench.
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Points to Malin for perfect deployment of a moto jacket and ripped skinnies. Little details (like a fringe purse and red tank) make it even more wearable.
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Yes, she’s wearing 50 shades of gray (give or take a few) but this monochromatic look pops thanks to the ombré detail on her Armani Exchange peacoat and that tomato-red bag.
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We've already told you time and again that it's totally kosher to wear white in the winter. Here's Jessica, wearing nothing but white, to drive that point home. Pay attention to how the weight of the fabric (a tactile knit, a soft denim) makes the whole look more seasonally appropriate.
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This is your ’90s trend revival, all grown up: Straight leg jeans, a chunky boot and beanie are all tempered by luxe fabrics and a fresh face of makeup.
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Send mental thanks to celebrities for continuing to demonstrate #325 ways to wear that turtleneck you got for Christmas. J.Lo gives hers a sexy (what else?) vibe with skintight jeans and knee-high boots.
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Tricky-to-wear statement shoes, like Eva’s ankle-tassel booties, work best when allowed to shine next to simple, neutral pieces (and yes, navy is a neutral).
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What do you get when you combine Drake's “Hotling Bling” turtleneck with skintight leather pants, mirrored Elizabeth and James aviators and model-off-duty pristine white kicks? One seriously cute outfit.
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Fringe, feathers and fur? It sounds like a lot, but in a streamlined silhouette and monochromatic color palette, Olivia proves it's a breeze to pull off.
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You may not have tons of places to wear a velvet suit, but when you do, you'll know exactly what to wear it with: a dangerously-low buttoned top with a little shimmer, a drop necklace and chunky heels.
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Dakota's ski-weekend chic can translate to your everyday life – a faux shearling-trimmed coat and Timberlands transform the most basic outfit into a chalet-worthy ensemble.
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Lupita's playful wide-leg Christian Siriano jumpsuit, with its crayon-like stripes, gets a little dose of toughness thanks to her moto jacket and bright red nails.
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Write “outfit covered” in the Friday box of your planner, because Kate's casual-chic look (comfy tee and jeans with slim-fitting blazer, polished flats and a chic bag) is going to take you from desk to departures at the airport.
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We're calling this monochromatic look, consisting of layers of soft, tactile fabrics with a touch of gloss in her accessories, “luxe on luxe on leather.”
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Who needs sparkles and spangles to turn heads at a holiday party? A sleekly sexy white dress (by KaufmanFranco) teamed with whiplash-inducing shoes (hers are Sophia Webster, and yes, those are butterflies) is guaranteed to be the most standout look in the room.
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The move that takes this from “supermodel off-duty” to “advanced supermodel-off-duty”? Coordinating the black-and-white graphic motif of her Tod's bag with her long cardigan from Express (worn with Black Orchid jeans).
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It's part chic snow bunny (the hat, mirrored Westward Leaning glasses and parka), part fireside hot cocoa sipper (the cozy cowlneck sweater), part urban explorer (the coated jeans and high-top sneaks) … and it's all super cool when worn together.
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Gigi continues to demonstrate acceptable ways to wear leggings in the outside world by choosing opaque styles (like this Alo Yoga pair) to wear under long sweaters (including her chunky-knit Faithfull the Brand turtleneck) and then choosing such kickass accessories you hardly notice her pants are spandex.
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C'mon, you know you wanna get that front-button denim mini out of the back of your closet. With a soft sweater, over-the-knee boots and an of-the-moment bag, your favorite style from high school gets an instant upgrade.
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The star's brushed wool notch-lapel coat and dove-gray boots give a luxe vibe to her simple ensemble of jeans, a black tee and a Tory Burch crossbody.
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A micromini suede shirt dress is undeniably sexy, but Ciara cuts the over-the-top hotness with a moto jacket and chunky biker boots.
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The black turtleneck-and-jeans combo is a classic for a reason: It's the perfect foundation for any look, including Lupita's boho-cool reversible MIH blanket coat, thick-framed sunnies and fedora.
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A busy mixed-print Proenza Schouler sundress gets a chic, taking-care-of-business upgrade from a sleek tuxedo jacket and some kickass studded lace-up heels (hers are Aquazurra).
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Leather leggings don't have to be all sky-high heels and plunging silk tops. Embrace their surprising comfort factor by teaming them with a cozy striped top, comfy sneaks and an oversized bag (but choose all black-and-white pieces to keep the vibe chic).
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You've got your favorite ribbed sweaterdress. You've got your favorite chunky-heeled booties. Team them together with tights and a pin-straight blowout and let the '90s magic happen.
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Of course, there's also this take on the look, which teams a white tee and bouclé jacket with perfectly-tailored dark wash denim and d'Orsay flats (say hello to your weekend uniform from now until the end of time).
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You know when people tell you a to break up a skirt suit and wear the jacket with jeans? This is exactly what they're envisioning, from the sweet jeweled Draper James top to the slightly distressed Mother jeans to the ladylike accessories (a plum Salvatore Ferragamo bag and navy J.Crew heels).
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Combining the world's coziest sweater (yep, that's cableknit and a turtleneck on her cashmere Design History style) with the perfect fall finds (a cranberry suede mini, croc-embossed Elizabeth and James bag and Ann Taylor booties), Tay may have just won the prize for “Best Autumn Outfit” with another month left to go in the season.
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Don't put away your white jeans just yet! They look great when paired with a thick, knit sweater and heels (hers are Jimmy Choo) in a dark color.
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We're really feeling navy as our go-to neutral at the moment, and here's a perfect example why: It's the perfect background to offset some seriously standout bright jewelry (like her David Webb earrings) without the harsh contrast black can sometimes have.
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