Several seasons ago I created a cheat sheet for the flop proof holiday party ensemble. The essential guidelines remain unchanged and the components of the formula are as follows:

Dressy dress + cover-up + heels + small handbag (hose is optional)

Creating a party outfit that’s fab for today AND several seasons into the future requires extra attention to details. If you choose the items carefully you’ll be able to wear the same timeless outfit year after year, perhaps changing the look slightly with a different arsenal of accessories each time. This approach to formal dressing saves you time, money and last minute holiday outfit stress. Obviously, if you’d prefer to change up your holiday look each year with a completely new outfit then that’s loads of fun too.

Audrey Hepburn DressAudrey Hepburn Dress

I thoroughly enjoy sporting the latest fashion trends in my every day style, but when it comes to formal wear, I like to look classic, retro and vintage because I adore the aesthetic and it won’t date. The dresses, shoes and accessories that you see in these pictures are many, many years old and still going strong. Some of the items were pricey, while others were moderately priced or dirt cheap, like the black floral feathered brooch on the strappy sequined dress which cost $4 at an H&M sale.

If you’d like to have a current and fun, yet timeless dimension in your party wardrobe capsule, these tips will help you on your way:

  • Pick an era: Dressy frocks with design features from decades like the 20’s, 30’s, 40’s, 50’s and 60’s are always in style because they look retro. Shopping vintage stores to get authentically old pieces from these decades can also be a fun experience.
  • Add the modern element: It’s important to add the “hip factor” to a classic, retro and vintage ensemble to keep things fresh and updated. At the end of the day you still want to look cool when you’re classic! This is easily achievable through accessories and in my case, my short mod pixie haircut instantly acts as one of these accessories. For the first full bottomed frock look, layering several strands of oversized pearls is very “now”. So is the clutch made of ruffled biker zippers that I matched with the red dress, while the bold geometric bag contrasts nicely against the vintage sequined frock.
  • Texture, texture, texture: Making sure your ensemble is texture-rich from top to toe is the most important part and I cannot stress this enough. This is what makes your outfit interesting and totally yours. Look for dresses and accessories that are made of interesting fabrications and mismatch these fabrications in one outfit. For example, choose a cover-up made of an iridescent texture especially when it’s in the same colour as the dress. Mix shiny with matte, hard with soft, and bright with neutral.

Finish off the look with a bit of party make-up and a trench or relatively dressy Winter coat (no puffers please). For me that means fiery red Chanel lipstick, darker brows and a black sateen trench coat with a huge silver buckle. I like to leave off my specs and chunky watch with this formula. My cell phone keeps the time and Greg becomes my eyes for the evening (no specs!).

Red DressVintage Hong Kong Dress