‘Tis the season of never ending holiday parties! That’s right, the next few weeks are guaranteed to be filled with lots of eating, drinking, and of course holiday cheer so it’s time to pull out your festive best. But all these events can make finding holiday outfit inspiration that isn’t repetitive (or cheesy) a bit of a challenge. Not to mention the weather outside is frightful this time of year, so having to factor in the cold and snow doesn’t help.

Unless all the parties you’re attending have an “Ugly Sweater” theme, you’re going to want to put on a little more than a sweater and jeans. If you’re like me you probably don’t want to be a holiday outfit repeat offender so finding all these looks can become a lot to put together and get expensive. I try and put together a little strategy for holiday outfit planning to help make this part of the holidays the fun one.

Holiday Outfit Planning Tips

1. Pre-Plan Your Outfits

Just like with any event or special occasion, I always like to pre-plan my outfits. When putting together a holiday outfit I first like to take a look into my close to see what basics or statement pieces I can use as a base. By doing this I tend to find myself saving a lot of money by using pieces I already own versus going out and purchasing an entire new holiday outfit.

2. Buy Separates You Can Repeat

If I do have to purchase a holiday outfit for an event, I try and purchase separates that I’ll wear after the event itself so I get use out of it. I also try and stick with items that are classics and not trends, so they can be re-worn for years. After all, there’s nothing worse then spending money on a piece you’ve worn once, only to find it in your closet years later and it’s no longer in style.

3. Consider Outfit Rentals

Got a holiday party that needs something a little extra special, but you don’t have the budget (or space in your closet) for it? Consider renting your next holiday outfit instead of going out and buying one. There are so many great rental companies online and in Toronto that carry designer label dresses at affordable rates. This is also a great way to be a bit more sustainable with your holiday outfit, by renting and not buying something you may not ever wear again.

Putting together a holiday outfit for someone like me who doesn’t tend to wear colour can bring up a new set of obstacle, with everything out usually there being merry and bright. But don’t stress out, there are a tone of fun ways to dress for holidays in a monochromatic look. From festive sparkle to cozy knits, a monochromatic holiday outfit doesn’t have to feel like a humbug. So I put together some all black holiday outfit inspiration to help you dress for any occasion this season.

Holiday Outfit Inspiration

For Work

My number one rule for any holiday outfit for a work party, is don’t wear anything you wouldn’t wear to the office. Go with something business casual yet festive like a sparkling knit sweater and velvet trousers. Got an office party that’s a little more glam? This look can easily be dressed up with a blazer or switch out the pants for a midi or maxi skirt!

• Zara Knit Sweater With Beading, $100
• H&M Wide-leg Velvet Pants, $60
• Jeffrey Campbell Siren Bootie, available at Nordstrom, $175
• Zara Velvet Belt With Detailed Metal Buckle, $36
• Seven Saints The Ultimate Gold Hoop Earrings, $55

For Friends

Getting together with friends for the holidays? Put together a holiday outfit that’s chic yet comfortable so you can focus on having fun, not fussing with your look. I always love a blazer thrown over a pair of jeans and a camisole for a night out on the town because of how effortless yet put together the pairing is. Throw on a Blair Waldorf approved sparkle headband for a little extra festive touch.

• H&M Double Breasted Jacket, $60
• Zara Lace Camisole, $40
• Zara Hi-Rise Straight Leg Jeans, $46
• Jeffrey Campbell Siren Bootie, available at Nordstrom, $175
• Zara Sparkly Headband, $30

For Family

What’s the holidays without spending time with family am I right? I always say go the cozy route with your holiday outfit for spending time with family, like a great pair of jeans and a knit sweater. If you’re family’s not the type to stay in, and you’re plans involve going out you can easily dress up this holiday outfit with a fur vest, riding boots and a wide brim hat.

• Love Token Velma Faux Fur Vest, $150
• Topshop Roll Neck Sweater, available at Nordstrom, $85/a>
• Zara ZW Premium Skinny Jeans, $50
• Zara Hat With Band, $46
• Sam Edelman Penny Leather Riding Boot, $210

Head to the style section for more outfit inspiration!