35 Perfect Street-Style Outfits for Any and All Party-Dressing Scenarios

This time of year can be stressful. (The shopping! The travel! The sun setting so early!) Thanks to street style, finding the right outfit for a holiday get-together really doesn’t have to be. Yes, there are a lot of parties to attend—from your office’s annual fete (where you really want to impress your boss) to that long-awaited high school reunion (it’s been how long?!)—each with its own dress expectation. But no matter what type of event you’re going to, there’s an outfit that’s already been road-tested by fashion’s most stylish set that fits the bill. Ahead, check out some fresh outfit ideas to inspire any (or all) of your party dressing.

Holiday Outfit Inspiration From Street Style: For the Office Party

A soft gray sweater and wide-leg, high-waist trousers are that perfect combination of easy and cozy. Wrap a second knit around your shoulders for good measure.

Holiday Outfit Inspiration From Street Style: For the Office Party

Think of this year’s office holiday party as your opportunity to kick your workwear up a few notches. Try a solid sweater and silk midi in an interesting color in lieu of your go-to gray. Mint is fresh but not too bright, making it a perfectly appropriate hue for an after-hours office soirée.

Holiday Outfit Inspiration From Street Style: For the Office Party

Yes, you can wear your skinny leather pants to a work event—pair them with a black knit top, black pumps, and a sick statement coat.

Holiday Outfit Inspiration From Street Style: For the Office Party

A structured red blazer is equal parts festive and powerful. Wear one with a pair of creamy trousers and solid pumps, et voil´`à—the perfect polished party look.

Holiday Outfit Inspiration From Street Style: For the Office Party

A pantsuit that’s got a little something extra—i.e., a leather look, elongated sleeves, an oversize belt—is a fine choice for your 9-to-5’s holiday gathering. Just add pumps.

Holiday Outfit Inspiration From Street Style: For the Office Party

When in doubt, stick to the classics: You can never go wrong with a tweed jacket, clean white tee, and some dark trousers.

Holiday Outfit Inspiration From Street Style: For the Office Party

Layer that silky floral midi that you’d otherwise save for after-hours over a mock-neck and what do you get? A perfectly appropriate office-party outfit that’s still out of the box and totally cool.

Holiday Outfit Inspiration From Street Style: For the School Reunion

It’s your [year redacted] high-school reunion—obviously you want to look damn good. Our advice? Keep it simple, with a few throwback-y staples: a leather mini skirt, creamy turtleneck, and buttoned-up blazer.

Holiday Outfit Inspiration From Street Style: For the School Reunion

Avoid looking like you actually tried and go the je ne sais quoi route: Think pale, slinky midi dress with an oversize contrasting jacket and ankle boots.

Holiday Outfit Inspiration From Street Style: For the School Reunion

A wrapdress is consistent and timeless, making it a fail-safe choice for a class reunion. Give it a modern spin with bright ankle boots.

Holiday Outfit Inspiration From Street Style: For the School Reunion

What’s more on trend than a slouchy pantsuit right now? Wear it with white Chuck Taylors and maybe even a beret, and you’re a shoo-in for best dressed.

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