Shoes: Madewell Leopard Skimmer ($135)

 From Left, Sunglasses: Kate Spade Oversized Retro Sunnies ($128) Earrings: Hive & Honey Hammered Studs ($14) Bracelet: Teardrop Cluster Bracelet ($13) Bag: J.Crew Biennial Satchel ($298) Belt: Vince Camuto Patent Turnlock Belt ($41) Wrap: Cashmere Wrap ($190) Shirt: Collection Draped Georgette Top ($198) Skirt: Theory Rita Pencil Skirt ($200)

From Right, Necklace: Lapis Scoop Necklace ($99) Necklace: Danielle Stevens Tortoise Chain ($85) Clutch: Kon Clutch (sold out in blue) Dress: Goat Lola Dress ($511)

Polyvore Set Here.

For a Business Convention.  This outfit was inspired by the glamorous of the 1940s and 1950s–the pencil skirt, the draped blouse, the cashmere wrap, the retro sunglasses.  But while the look may have an aura of old Hollywood, these pieces are classics that combine to create a chic and cozy work look.

I love the neckline on this blouse.  It’s flattering on a number of figures, and while it looks lovely on its own, it would look incredible under a one- or two-button blazer.  I would tuck it into the pencil skirt and wear the belt at the top of the skirt, just overlapping the blouse.  Need a cheaper pencil? Michael Kors makes a $70 version.

I added the cashmere wrap because convention halls are notoriously chilly.  You can roll it up in your purse, and pull it out when you get cold.  It’s an elegant alternative to stealing the hotel comforter and wearing it around (this is not a joke, I’ve seen this).

I’m still in love with my Biennial satchel, and the divided pockets make it an ideal travel bag.  If you need a less-expensive red bag, try this satchel from Express.  I chose the bracelet so that the outfit would have a bit of color even when you’re not carrying the bag.  And the sunglasses are an interesting retro shape.

For the hair, I would definitely wear it up.  My hair looks best twisted back into a bun, but you could also wear a French twist or a low-side bun.  For the makeup, keep it simple with neutral eye makeup, black liner and a flattering rose blush.  I’d also paint my nails red to match the bag, or pale pink if the convention attendees are very conservative.

For a Dinner Date.  This outfit is stylish and modern, but also relaxed.  The shift dress has a looser fit and the flats keep your feet happy all night long. It’s perfect for a dinner out with friends, a dinner date with your boyfriend/husband or a birthday dinner.

I love yellow and leopard together.  It’s a bold combination that looks effortlessly chic.  If you like this dress but can’t afford $500+ for a dress, Banana Republic has a dress that I like even better for $140.  If you use promo code BRFASHION save 30% until Midnight.

I wanted to liven up the outfit and I thought that a deep, almost navy blue was my best option.  So I paired a lapis pendant necklace with a long tortoise chain to add shimmer, color and texture.  Then, I added the blue clutch so pull it all together.  This clutch appears to be sold out, but the Crowston clutch from Aldo ($35) would also work.

For the hair, I’d wear my hair down and stick straight, or pull it back into a low sleek ponytail with a teased crown, covering the elastic with wrapped hair.  For the makeup, I’d wear cat-eye black liquid liner, a light wash of gold shadow (I like Stila Oasis) and red lips (MAC Ruby Woo).