Related: What to Wear to Holiday Parties 

Down vest with raccoon trim by Missoni, $495
Sarah Goodall, owner of the ultra-chic shoe boutique Saucy Shoes in Annapolis, says she’s preordered this super-soft vest by Missoni from next-door neighbor Laura Bevilacqua. “I live in vests in the winter,” Goodall says. “I think it’ll look very chic with a pair of dark skinny jeans and my knee-high Cynthia Vincent brown Lizard Riding boots—from Saucy, of course.”

Beth Havrilla, 27
Fine-art painter

Jennifer Lasher, 26
Solo musician

On Beth: Anthropologie coat, Urban Outfitters scarf, vintage lace gloves, Marc Jacobs bag, H&M tights, and shoes from Anthropologie.
On Jennifer: Coat from Burlington Coat Factory, Salvage shirt, Wal-Mart tights, leg warmers from Up Against the Wall, Nine West boots, and earrings from a boutique in Annapolis (“I don’t remember which one”).

How would you describe your style?
Beth: “Audrey Hepburn if she were six years old!” (Jennifer calls Beth a “modern Mary Poppins.”) “Classic and definitely girly. I’m a total magpie.”
Jennifer: “Boujie goth.”

Monday, December 1: Come out to the Lexus and Essence magazine Arriving in Style trunk show, a private showing of Kevan Hall’s 2009 spring collection, hosted by Holly Robinson Peete. Proceeds benefit HollyRod4Kids, a nonprofit organization dedicated to improving the quality of life for underserved children. The event, held at the Reagan Center, includes a cocktail reception at 7 and a fashion show at 8. RSVP to rsvp@luxuryawaits.com.

Thursday, December 4: From 5 to 8 PM, stop by the men’s clothing store Everard’s West End location for its Holiday Shopping Day Event, where you can shop, drink wine, and snack on hors d’oeuvres. RSVP to everards1@aol.com.

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If voting wasn’t enough, now you can show your love for Barack Obama with a bit of bling. Washington jewelry designer Ann Hand has created a Barack Obama collection to commemorate the historic inauguration.

For $95, you can score a glitzy silver necklace featuring Obama’s name written in 84 Swarovski crystals. Bling not your bag? Hand also has Obama watches, sunglasses, cuff links, dog tags, and pins. Her favorite item is a blue Obama 2008 travel mug with six rows of rhinestones for $25 (currently out of stock).

The Little Black Dress

Although the little black dress never goes out of style, it’s back on the top of trend lists this season. Balenciaga set this trend with a series of structured black dresses that pinch in at the waist and go out around the hips. This silhouette, which emphasizes the shape of a woman’s torso, was seen all over the runways this season in dresses, jackets, and tops. Find a little black dress with these lines and you have a fashionable yet classic outfit that can transition easily from a work function to a family affair to a night on the town. The Balenciaga dress is hard to come by in Washington, but here are a few charming alternatives.

Jennifer Cross, 28.
Personal assistant by day, printmaking artist by night.

What she’s wearing: Bettino Liano blazer from Australia (she lived there for two years), Silence + Noise top and leggings (“great designs that are beautifully made with a vintage feel to them”) from Urban Outfitters, Bakers shoes, L.A.M.B. bag, Jessica Kagan Cushman bracelets from Neiman Marcus, and hair by Remi at Salon one80 (“I don’t let anyone but Remi touch my hair”). The tattoos are from Susan at Jinx Proof in Georgetown.

So those leggings look like leather but they’re not. Are they comfortable?
“They’re surprisingly comfortable and warm. I have two pairs!”

How would you describe your look?
“I don’t really have a specific style; it really depends on my mood. If I’m going out for a specific event where I need to dress it up a bit, it usually ends up looking glamour-rock with a vintage clutch. But on an everyday basis, you’ll find me in a pair of super-skinny tapered jeans, a T-shirt, light jacket, ballerina flats—I live in flats—and a big purse. I’m Mary Poppins. I’m attracted to things you wouldn’t find on anyone. I never shop for an outfit; it’s usually me buying a piece here or a piece there, then I throw different pieces together and pray it works.”

Through Sunday, November 30: You can always use a new pair of jeans, right? National Jean Company’s two local shops (Reston and Bethesda) are giving shoppers 30 percent off the highest-priced item they buy and 20 percent off additional purchases. Don’t miss this opportunity to get discounted designer denim!

Friday, November 28: Bloomingdale’s in Tysons Corner Center is hosting an Abby Joy Jewelry trunk show from 11 to 5. Each piece in the collection is made with a hand-sculpted wax mold and then crafted into silver or gold. Also, each piece has a designated charity that receives 5 percent of the price on each sale; abbyjoy.com.

The Dupont Circle boutique Green and Blue is starting its monthlong holiday sale on Friday. There’ll be 20 to 50 percent off on winter pieces from designers including Rebecca Taylor and Yoanna Baraschi. Sale ends December 31.

The shops of Bethesda Row are hosting a Black Friday fashion sale. There’ll be carriage rides, hot chocolate, and discounts. Tickled Pink will be offering discounts all day, and Urban Chic and Ginger boutique will offer 50 percent off from 9 to 10 AM, 40 percent off from 10 AM to 1 PM, and 30 percent off during the rest of the day and through November 30.