Even the most fashion savvy haven't tried every outfit combo in the book, but those itching to try their hands at a few new style tricks will find that the holiday season sets up the perfect occasion. For starters, you probably have more than one event providing you an excuse to get dressed up, and over-the-top outfits are often expected. Why not take this time to test out experimental garment pairings you may not try on just your average Friday night?

If you look to a few street style mavens as inspiration, you'll find that the options are virtually endless, and plenty of looks can likely be created with items you already have in your closet. Whether you're headed to a grand gala, a large family gathering, or an intimate night in with friends, here are a few unexpected holiday outfit ideas [1] everyone else will wish they'd thought of.

Tip 1: Marry a Light, Feminine Dress With Dark, Edgy Shoes

Edging up an ultrafeminine look with a grungy flare remains an easy trick to add excitement to your outfit, yet it translates as expert-level. For a festive daytime event, throw on a light-hued maxi dress with soft, ruffled details, then juxtapose it against chunky boots for an unexpected turn.

Veiled Collection Alessia Ruffle Maxi Dress

Veiled Collection Alessia Ruffle Maxi Dress [2] ($139)

Steve Madden Cobra Leather Booties

Steve Madden Cobra Leather Booties [3] ($160)

Tip 2: Go Ahead, Wear Sweats . . . and Heels

Chilling out at home for the holidays, but want to feel done up? Or perhaps you just want to take a comfort-first approach to stepping out this season? You can totally throw on your favourite elevated sweat set. This time, pair it with metallic heels that will make everyone forget you're not wearing a blazer and trousers.

Nap Repose Set

Nap Repose Set [4] ($88, originally $135)

D'Accori Roux Sandals

D'Accori Roux Sandals [5] ($928)

Tip 3: Mix Leather and Sequins

Sequins and leather are an inherent match . . . said no one ever. But this season, they can be. Great for a chilly holiday dinner outdoors, team up a glitzy minidress with an oversize faux-leather jacket for an effortless and festive rocker-chic vibe. There's an outfit you don't see every day but will definitely want to wear again.

Zara Knotted Sequin Dress

Zara Knotted Sequin Dress [6] ($50)

Lioness Staten Island Jacket

Lioness Staten Island Jacket [7] ($84)

Tip 4: Pair an Ultrastructured Top With Fluid Bottoms

For a more subtle play on opposites, try pairing a sharp, bold-shouldered top with baggy bottoms. You don't have to go, say, full-on sweatpants or traditional cargos. Instead, you can keep the look elevated with a pair of cargo-inspired silk pants. The end result is an outfit you won't feel out of place wearing at a formal soirée but will still allow you to enjoy free movement on the bottom.

Annakiki Rised Sleeves Detailed Shirt

Annakiki Rised Sleeves Detailed Shirt [8] ($302)

Cult Gaia Wynn Pant

Cult Gaia Wynn Pant [9] ($458)