The Classic: Denim Jacket

Denim jackets will never go out of style, putting them at the top of our list. A good denim jacket compliments pretty much any outfit. Pair a denim jacket with your favorite dress or top to really complete your outfit.

You may be getting Britney Spears and Justin Timberlake circa 2001 vibes from this next suggestion, but if you’re in the mood to try something new, pair your denim jacket with denim jeans to complete the classic Canadian Tuxedo. Who knows, you may just find your new favorite outfit.

Rough & Tough: Leather Jacket

While maybe not the warmest, a leather jacket makes a great addition to nearly any outfit. A good leather jacket will bend and mold to fit you perfectly, making it the comfiest thing in your outerwear collection. If you’re not into leather jackets yet, start out with a moto jacket. Moto jackets are usually slightly shorter, more fitted, and feature zippers or stitching to add a little something to the design. Moto leather jackets are the perfect way to wear a more feminine leather jacket while still letting you tock that classic leather look. Pair with jeans and heels and you’re ready to rock the town.

Rough & Tough: Leather Jacket

While maybe not the warmest, a leather jacket makes a great addition to nearly any outfit. A good leather jacket will bend and mold to fit you perfectly, making it the comfiest thing in your outerwear collection. If you’re not into leather jackets yet, start out with a moto jacket. Moto jackets are usually slightly shorter, more fitted, and feature zippers or stitching to add a little something to the design. Moto leather jackets are the perfect way to wear a more feminine leather jacket while still letting you tock that classic leather look. Pair with jeans and heels and you’re ready to rock the town.

The Adventurer: Puffer Jacket

A puffer jacket is a surefire way to stay warm while still maintaining your style dignity. Puffer jackets are easily identifiable by their quilted type design that creates puffy sections between the stitching. Women’s jackets may be slightly tapered at the waist compared to men’s jackets. They are extremely lightweight, yet very warm as they are filled with down insulation or synthetic fibers. These jackets are the perfect blend of lightweight and warmth. Pair your puffer jacket with everything from heels and a flowy top, to come chic adventurer boots and jeans.

Handy Dandy: Cargo Jacket

Cargo jackets are the perfect staple piece for any outfit. One style of cargo jacket that you’ve probably seen everywhere: army green. These babies have taken the fashion world by storm. They are by no means new to the fashion scene, but these utilitarian type jackets are going through a major trend right now and we hope it never ends. These jackets are perfect for pairing with any outfit, from your grocery store, leggings and hoodie look, to your going out, weekend outfit.

Oh So Fly: Bomber Jacket

If cargo jackets gave you any hint, bombers sealed the deal. Utilitarian outerwear is so in right now. Bomber jackets are styled similar to the jackets pilots and flight crew wear.

The lining of these jackets ranges from relatively unlined to heavily lined with warm materials like sheepskin.

Pair your bomber jacket with jeans, a tee, and sneakers, or try a fun twist by swapping those jeans and tee out for a tee-shirt dress for a killer combo.

Boss Girl: Blazer

Blazers are so in right now. They can be used in a business or office setting, or just worn as an urban outfit.

Solid colors or design–like this plaid blazer–are perfect outfit choices.

My advice: get something you can wear with multiple outfits. You'll love the blazer look, and you'll love it even more when you make it a part of your normal rotation.

Slide up the sleeves to get that modern, casual look or keep the sleeves full length to keep it office-appropriate.

On Cloud 9: Sherpas

Sherpas might be the softest, comfiest jackets around. If you have ever felt one, you'd know it too.

They usually have a quarter zip which means what you're wearing under still shows! A turtleneck and a short necklace are a great styling combo to go with your new favorite sherpa.

I love my sherpa and every time it gets cold, there is a good chance you will see me rocking it.

Casual and Comfy: Zip-Up Hoodies

Hoodies are a staple of cold weather but they can feel so low-effort that people shy away from them sometimes.

Having a zipper on your hoodie makes it a jacket, which makes it less low-effort feeling. With a pull-over hoodie, that's all you get to style with, but a zip-up hoodie, you can use what you wear under it to make the style better.

Style your zip-up with a simple t-shirt and your favorite necklaces to look a little styled up on a lazy day.