So you’re deeply invested in wowing your boss at the company holiday party. Simply wearing something you’d otherwise never be seen in at work won’t cut it. The trick to nailing this particular dressing scenario is to take your typical 9-to-5 to a better place: choosing a pantsuit in an OTT color, for example, or swapping out a buttoned-up blazer for an edgy leather moto while keeping the pencil skirt. It’s surprisingly easy to play around with your tried-and-true, polished and professional staples, all while staying within the dress guidelines. We found 30 street-style examples that are right on target for an office holiday party outfit that’s memorable in the best way.

A pretty lace skirt feels a lot less serious when you play it down with a distressed leather jacket and red ankle boots.

Pantsuits for work? Groundbreaking. But one bedecked in a killer print and layered over a classic Breton-stripe? Actually awesome.

A micro-pleated midi is always polished and professional. Choose one in a cool color and pair it with a crisp, colorblocked crewneck.

Break up an all-black office lewk with a fun furry jacket and an itty-bitty bag in your favorite shade.

Double up on button-downs, then link them up with a classic checked skirt. Go with solid accessories for a super-sleek finish.

It’s time to break out that oversize suit you’ve been waiting to wear with your go-to white T-shirt.