What To Wear To Your Office Holiday Party, On a Brunch Date + When You Might Be Seeing Your Ex

Marie Claire's Fashion Editor-at-Large, Zanna Roberts Rassi knows a thing or two about how to majorly up your style game — with minimal effort. 

For her latest fashion challenge, we set her up with one of our viewers, Kai, who admits she pretty much always wears the same kind of outfit, no matter the occasion. (And while a sleek, monochromatic look might be a staple here in NYC, you can always dress up a black outfit!)

There are three basic things to consider when choosing an outfit, Zanna says. First, where are you going? Secondly, who are you going to be with? And finally, how do you want to feel?

To help demonstrate, Zanna and Kai are playing a game we're calling "Spin For Your Style," which involves a giant wheel with options for each of these questions. Kai "spun" the wheel three times, and Zanna ran with the random selections and styled three different outfits for each of the three very different occasions.

Check out the final looks below, and click to shop all the items at Banana Republic.

How To Dress Up For Your Office Holiday Party + Still Feel Comfortable

LOOK 1

Where are you going? Holiday party
Who are going to be with? Co-workers
How do you want to feel? Comfy

Not only is this velvet jumpsuit comfortable and dressy, but it's also elevated enough to impress both your boss and your co-workers.

Rachael Ray Show

SHOP THE LOOK
Velvet Cowl-Neck Jumpsuit, $149
Houndstooth Double-Breasted Car Coat, $279
Embellished High-Heel Mule Pump, $128
Classic Rebel Cup Chain Layer Necklace in Silver, $48

How To Dress For A Casual Brunch Date + Still Feel Sexy

LOOK 2

Where are you going? Brunch
Who are going to be with? Date
How do you want to feel? Sexy

The sneakers in this outfit keep it casual and comfortable for a weekend, but the bright yellow sweater and high slits up the sides of the maxi skirt make a memorable statement.

Rachael Ray Show

SHOP THE LOOK
Maxi Skirt with Side Slits, $98.50
Chunky High Crew-Neck Sweater In Neon Yellow-Green, $98.50
Leather Convertible Belt Bag in Black Leather, $98
Essential Leather Sneaker in White Leather, $138

How To Dress For A Birthday Party Where You Might See Your Ex + Feel Powerful

LOOK 3

Where are you going? Birthday party
Who are going to be with? Exes
How do you want to feel? Powerful

Rach says it all for this powerful outfit that would make any ex do a double take. "You look like the birthday party," she says. We agree!

Rachael Ray Show

SHOP THE LOOK
Red Leopard Print Puff-Sleeve Wrap Dress, $139
Embellished High-Heel Mule Pump, $128
Classic Rebel Cup Chain Layer Necklace in Silver, $48