If you have a question for the Preppy Girl email it to me at preppygirl@thepreppylife.com.

Dear Preppy Girl

I seek your wisdom here. My wardrobe has been classic preppy for as long as I can remember. Polos, oxford shirts, critter print, cardigans, Lilly dresses, the whole deal. However, my 21st birthday is coming up soon, and I’ll likely be sampling the local night life. I know that my usual outfits probably won’t fit the sexier vibe of the chic lounges and martini bars I plan on checking out, but I want to avoid the usual trashy and flashy night life apparel. I’d much rather keep it classy. Any tips for selecting prep-worthy outfits for a night on the town?

Sincerely,
Preppy Girl Going Out

Dear Preppy Girl Going Out,

I think the key to looking fabulous is the silhouette. Keep your outfit simple for example sporting a “fancy” top with a pair of cropped pants. I love J. Crew’s Minnie pant coupled with ballet flats. Anthropologie also has some great looks for fall.

• If you are feeling more casual, try pairing a pretty tank or cami with a long cardi and a great pair of jeans and heels.
• Or try a more sophisticated monochromatic look using fun accessories to add pops of color to your outfit. For example dressing up in shades of silver and gray but wearing a boldly colored jewelry and an eye-catching handbag.
• If all else fails, a little black dress with a cute cardi works every time.
• Remember to wear comfy shoes in case you want to hit the dance floor.

I personally love to channel Audrey Hepburn, my style muse, when I get ready for a night on the town.

Have a happy birthday!
P.G.

If you happen to be in the Baltimore area, I suggest checking out Baltimore Ghost Tours. They offer haunted history walking tours of Fell’s Point and Mount Vernon, two of Baltimore’s oldest and spookiest parts of town. Learn the ghost stories behind these beloved Baltimore neighborhoods. Haunted pub walks are also available if you want to get “close and personal with the spirits.”

Named “Best Creepy History” by Baltimore Magazine, 2009, The Original Fell’s Point GhostWalk and Mount Vernon GhostWalk are great ways to experience the supernatural side of Baltimore. The tours fill up fast, be sure to reserve your space today! Visit Baltimore Ghost Tours web site to learn more: www.baltimoreghosttours.com.

Need a Halloween costume?
Click here for The Preppy Life’s fav preppy Halloween costumes.

The Met's Rooftop Garden

Must be nice!

For dinner we took a taxi to the West Village and had dinner at La Ripaille, a charming French restaurant with fabulous food and service. For dessert we walked to the famed Magnolia Bakery and stocked up on cupcakes: banana, chocolate, and butter cream. We headed back to midtown, ate a few cupcakes, and checked out the bar scene.

Our hotel in midtown Manhattan

On Saturday we did a little shopping and even stopped by the Mothership a.k.a. Tiffany’s flagship store. Sadly, I didn’t buy anything. We also cruised through Coach, H&M, Channel, Bloomingdale’s, and Burberry before hitting the road. It was a whirl-wind trip but I had a blast. Hoping to go back soon!

• Toga! Toga! – Beloved costumed straight from Animal House. Tommy Bahama sheets optional.
• Audry Hepburn ala Breakfast at Tiffany’s
• Sailor – Everyone loves sailors, the preppiest of costumes. Grab a striped shirt and your boat shoes and you are all set!
• Michele Obama – Super preppy role model
• Spy – Great excuse to stay warm and wear your Burberry raincoat
• Valley Girl – 1980s style
• Private School Student – Wear your old uniform, even better- wear your old gym uniform! This only works if you are past your high school days.
• Lacrosse Player – Everyone loves a lacrosse player!
• Your Parents – Hardcore Preps
• The Shopaholic – Carry a bunch of shopping bags from Bloomingdale’s, J. Crew, and Tiffany’s

Secondly, you can now put out the pumpkins without fear of being tacky, but please wait until the evening before Halloween to carve them.

Lastly, it is a great excuse to throw a wicked costume party, togas optional. Stayed tuned for more Halloween fun including my top ten preppy Halloween costumes.

Trendy twenty-something prepsters spend their weekends navigating the murky waters of summer shares. On the weekends, you can spot them in preppy beach towns, such as Dewey, trying to enjoy their 1/32nd of a beach house. The main attraction of a summer share is seasonal access to preppy watering holes such as the Bottle & Cork, a cute place for hobnobbing with DC’s future lawyers and politicians. Summer is not complete unless you hook-up with at least one aspiring lobbyist.