Where do the pretty things go after work? How do they dress to impress when hitting the town for some serious clubbing, taking in some culture at a local museum, or just seeing where the night takes them with a posse of gal pals? What are their face-time beauty secrets? For answers, we partnered with Dior and some of the chicest ladies we know for nightspot recommendations, winning wardrobe tips, and killer beauty strategies for any social-hour situation.

Our insider look at how to primp and dress yourself for any occasion comes from a duo of angel-faced, hard-dancing musicians, Chess Hubbard (aka DJ Mother Hubbard) and Jessica Gonyea (aka DJ A-Cup) of Moneypenny. As Chicago club queens and tour-mates, these partners in crime have learned how to own a room, be it an underground disco or an above-ground experimental theater.

There's no denying that we swoon for a beautiful pair of shoes. But something that feels good, too? You just can't beat that! We've got a pair that covers all the bases, and has a way of giving back that makes them the ultimate accessory. BucketFeet, the brainchild of two volunteers working with children in South America, are adorable, lightweight slip-ons with tons of heart. In the process of creating something functional and honing in on the designs of hot up-and-coming artists, BucketFeet also gives back 5% of all sales profits to children in need through the support of non-profit partners Children Mending Hearts, MAGIC, and love.futbol. The premise is simple: For $60, you can own a pair of these cuties and be a part of the cause to empower youth through art, music, and sports. And because BucketFeet has such generous ethics, they've also teamed with R29 to treat one special winner to a pair of BucketFeet. Pick your choice of the wearable art and while you're at it, you'll also be gifted a $400 shopping spree with endless possibilities for how to spend it. Don't drag your feet on this one, the last day to enter is August 29!

What's your ideal Chicago evening? On our agenda would be a delicious meal, tasty cocktails (plural, not singular), good company, and, of course, the perfect ensemble that will make your date do a double-take. Along with our favorite foodie resource, Tasting Table, Refinery29 wants to give you that very spectacular night. So, put that wallet away—it's on us! Whether you want to celebrate a special occasion, or don't need an occasion just to celebrate, we are here to equip you with all the makings for a night to remember, so enter for your chance to win dinner for two at your favorite Chi-Town spot. And in addition, we'll hand over $300 to outfit you head-to-toe. Enter today for your chance to win a night you'll never forget with a tab you'll never have to pay.

What's the one must-have item for celebrities? Mansions, cars, boats, designer clothes? Nope. It's status sunglasses, specifically Grey Ant's Status shades. The overgrown Wayfarers have been spotted on all the big names from Beyoncé to Lady Gaga, and is a bestselling item at ShopAKIRA, the online fashion retailer with the latest on clothing, shoes, and accessories. Refinery29 and ShopAKIRA have teamed up to grant instant celeb style to one lucky reader by giving away a pair of Grey Ant Status sunglasses. Sign up for both Refinery29 and ShopAKIRA newsletters and like us both on Facebook for your chance to win. For more of the latest trends, check out ShopAKIRA, which has their own label brand, AKIRA, along with many other popular brands such as Jeffrey Campbell, House of Harlow, and Sam Edelman.

With design creds including Elizabeth and James, Alice & Olivia, and Barneys, Ann Yee was no stranger to successful clothing lines before launching her own in 2009. Drawing inspiration from "everything and anything," the New York transplant from Michigan credits downtown street style, art exhibits, and movies to have sparked her creativity, and describes her aesthetic as geometric and architectural.

While we love Yee's beautifully structured clothes, she assures us they haven't come without hard work, especially for an independent designer in such a competitive field. She credits three traits to make it as an independent designer: patience, taking criticism gracefully, and standing up for yourself. And of course a fourth--endurance (she's no stranger to sleepless nights and a non-stop work day).

Whether you've heard some buzz about Yee or spotted one of her tops on Good Morning America (her current claim to fame, until the day she spots a "stranger in the street" wearing her clothes, the designer says), FashionStake and Refinery29 are helping you add some Ann Yee originals to your wardrobe. If you haven't heard, FashionStake is a crowd-curated marketplace for independent fashion that currently carries over 200 designers.

Simply enter below for your chance to win the Ann Yee Tova Draped Jumpsuit, a beautiful, super-flattering, silk, navy one-piece perfect for transitioning from day to evening.

Sometimes Mom's voice still rings in our head as we're walking out the door, "Take a jacket, you'll get cold." These spring days can be so misleading with the warm daytime temperatures dropping in the evening, not to mention those pesky, unpredictable rain showers. With your well-being in mind, Refinery29 has teamed up with Penfield USA, the classic outdoor apparel brand, to give one lucky reader their lightweight and weatherproof Rider jacket. The Rider is diamond quilted with naturally breathable material, a classic jacket that can be worn over any outfit, keeping you stylish while being sensible. Just enter your email address by May 12 to sign up for Refinery29 and Penfield USA newsletters to be entered to win. Check out Penfield's Women's collection for more timeless spring essentials that's equal parts style and function.

Celebrate Anglophilia with well-heeled style at Owen and Engine, Chicago's answer to the Brit gastropub. Logan Square may not be the first area Angophiles head to for an authentic Brit pub atmosphere, but the neighborhood edition is a perfect, homey edition for those hopping off the Kennedy in need of a little comfort food. A joint effort headed up by the owner of Fat Willy's Rib Shack (a great place to get a little messy) and a former chef at MK Chicago, neither purport to do incredibly authentic "British" food. Instead, they teamed up to make a friendly gastropub, with in-house smoked salmon and house-cured sausage with beer mustard soaking up hand-picked drafts and ales. Of course, classics like bangers and mash, fish and chips or Yorkshire pudding appear, but the off-the-beaten-path selections like cauliflower soup with a parmigiano reggiano and chive garnish or pan-seared sea bass with braised endives keep the fare from treading into blood pudding territory. No pinky-up wine sipping tonight—the beer selection is formidable—but keep things refined with British-inspired tailoring, like a smart jacket, a cozy cardi or pleated pants for the evening.

Owen and Engine also is known for their meaty and rib-sticking brunch fair, so put on a pair of chunky, but not super high heels for Saturday strolling and enjoying the curious culture clash of a gastropub on Western Avenue.

Owen and Engine, 2700 North Western Avenue (At West Schubert Avenue). (773) 235-2930.

Clockwise, from top left: J.W. Hulme Excursion Chaperon Bag, $690, available at La Garçonne; Dior Addict Lipstick in Fashion 754, $28, available at Dior; French Connection Summer Thistle Dress, $128, available at French Connection; Rebecca Taylor Stretch-Wool Double-Breasted Blazer, $395, available at Net-A-Porter; Rachel Comey Wane Clog, $345, available at Solestruck.