How to Dress Stylishly while Staying Warm in the Fall Season

Living in Canada, where it gets cold eight months out of twelve months, you can’t help but make sure your wardrobe is in order whenever the fall and winter seasons come along. 

Depending on where you live in Canada, your choice of outfits during the last and first quarters of the year might vary. But chances are that choice is very limited, and you may find that it’s challenging to be stylish when you’re just trying to stay warm.

The typical Fall and Winter season essentials include sweaters, pants, joggers, hoodies, boots, and coats. Considering how much warmth and comfort are needed during these seasons, these clothing items are useful. But you might need some help styling these items in a way that allows you to express yourself and show your personality. 

The good news is this article explores five ways that you can style your fall and winter outfits, so you never have to wear the same thing twice during these seasons. It also includes tips that you should keep in mind when cloth shopping for the fall and winter seasons. 

Here are five ways to dress stylishly while staying warm during the Fall and Winter seasons: 

  1. Repurpose your summer outfits.

When preparing for the fall months, it’s tempting to only buy clothes that will last you through the end and beginning of the year. But I highly recommend that you shop for clothing items that you could potentially wear all year round. For example, there are sweaters that you could buy in the fall that might provide much-needed warmth for a summer evening by the lake.  

Similarly, you can repurpose clothing items worn in the summer but add extra layers to keep you warm. For example, you can wear a slip dress with an oversized sweater or a turtleneck top over the dress. You could also wear a midi slip skirt with an oversized sweater. The main idea here is to prepare for the fall season with the other seasons in mind.

2. Fitted Outfits

When shopping for items like pants, skirts, or dresses, it is best to choose fitted ones because they have limited space for you to feel the cold. This is a must if you live in a colder region. Although wide pants or culottes are trendy right now, you want to make sure you’re wearing clothing items that are comfortable for you and fit your personal style. Also, you want to stick to pencil and a-line skirts instead of flowing skirts and dresses. 

3. Invest in Accessories

Accessories elevate an outfit, and during the colder weather, I recommend every opportunity to make yourself feel and look good. Accessories like hats, scarves, gloves, and shoes are common winter pieces you can pair with, or use to complement, different outfits. Think about how you’re pairing them and if the combination of those pieces gives you the look you’re going for.  

You can throw on a hat to give an elevated chic look while keeping your head warm. Use scarves with bright colors or patterns, add more in-depth to neutral-colored outfits, and keep your neck warm. Or buy gloves that pair well with formal outfits and tights that fit your pencil skirts. Whatever you do, consider the type of accessories you’re buying and how they fit with everything else in your wardrobe. 

4. Purchase Wool Clothes

Most sweaters, that we wear in the fall and winter seasons, are made using wool—specifically merino and cashmere. Wool is great for thermo-insulation, which means that it can keep your body warm when the weather is cold and cool when the weather is hot. It’s perfect for regulating your body’s temperature. As you buy outfits for the fall season, make sure you know what your sweaters and thick clothes are made out of, and be sure that they can keep you warm when needed. 

5. Wear long, statement cools

Coats are the most important layering piece you could probably buy and wear in the fall and winter seasons. They pair well with just about any other clothing item and can keep feeling warm while looking stylish. You should have at least a couple of these long, statement coats that you can rotate over the cold season. 

My first fall and winter months here in Canada were challenging for several reasons. I made several poor choices when buying outfits for those cold months. I bought jackets and boots that were simply too heavy, not warm enough, and definitely not stylish. 

But over the years, I’ve learned what to do and what not to do when shopping for the fall and winter seasons. I’ve shared some of what I’ve learned in this article, so I hope that you’ll find these tips helpful.  

Stay warm, stay stylish. 

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How to Style and Wear Your Sweaters this Fall Season

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6 Types of Sweaters to Style in Fall 2022