5 Must-Haves to Transition Your Wardrobe from Fall to Winter

A photo of sweaters stacked neatly on a wooden table.
Photo by Sarah Shull on Unsplash

Not only does November bring us closer to the holiday season, it also gives us the chance to transition our closet from fall to cozy winter clothing. Updating your closet doesn’t necessarily mean you need to pour your money into stores like Aritzia or Urban Outfitters. In most cases, thrift stores and vintage shops will be the perfect place to find stylish, sustainable and wallet-friendly items. Whether you are staying inside this transitional season, working as an essential worker or trying to pull some new looks and have a fashion show at home, here are five pieces of clothing that will make the switch to winter quick and easy. Plus, they all go great with a mask.

1. Cable knit sweaters

I assume we all saw photos of Chris Evans wearing a cable knit sweater in Knives Out this last year and absolutely fell in love. Mainly with the sweater, but Chris was a bonus. If, like me, this fall season you resorted to the comfort of a light cardigan, a cable knit sweater might be just the thing you’re looking for. These sweaters are delectably cozy since their thick wool provides a nice coating to your arms, whether oversized or fitting.

Actor Chris Evans in Knives Out (2019) courtesy of Men’s Health Magazine

2. Turtlenecks

It’s no secret that turtlenecks have made a big comeback in the past few years. They are great on their own in the fall and once winter hits, they’re perfect for layering. You can wear one under crewnecks, crop tops, low-cut tops and more. There are so many possibilities! I suggest having at least one solid black turtleneck and one solid white one just as basics and then you can begin to experiment with different colours, sizes and patterns.


How do you guys style turtle necks?#fashion101 #turtlenecks #thrifted #myoutfit

♬ a lot of money in the grave by auxtin marc – outfits ✘ anime

3. Tights

A simple way to incorporate skirts, dresses and even shorts into your winter wardrobe is to wear a pair of tights underneath. There are many different thicknesses, patterns and colours you can try that will both spice up an outfit and keep your legs toasty, especially during this transitional weather. 

Black translucent tights with a white dress via Instagram @bestdressed

4. Socks and heels

I know what you’re thinking, “Socks and heels, are you insane?!” and I’m here to tell you that this stylish little detail is the perfect way to get a final use out of your summer sandals during this transition. Pairing a warm sock with a strappy sandal highlights the beauty of the shoe all while keeping your toes warm. This trend may not be for everyone, but just remember you can experiment with different heel heights, sock colours and styles and so much more in order to fit your personal style and comfort. Once the snow hits, switch out the heels for a delightful pair of boots!

Ivory socks paired with tan heels via Instagram @pameluft

5. Beanies and other warm hats

Traditional bucket hats, baseball caps and headbands are unfortunately no longer useful during this season. Just like our body, our head needs to be covered too, which is why a beanie or thick beret is going to be great for transitioning your wardrobe. Beanies are great for everyday use like hitting up the local grocery store or taking your dog out for a walk. If you’re looking for something a little different, fuzzy bucket hats, such as the one pictured below, are made of a thick plush material and will be a great swap! 

A winter outfit with tan beanie via Instagram @orionvanessa
Model Bella Hadid wearing a fuzzy bucket hat courtesy of Glamour Magazine