What to Wear for a Fall Trip to Windsor, Ontario

Got a fall trip planned to Windsor, Canada? Windsor can be fun to visit in the fall, but you'll want to make sure you're dressed right. The weather is mild and dry, with temperatures averaging around 61°F (that's 16°C). So what should you wear so you can stay comfy and fit in with the local vibe?

To make the most of your trip to Windsor, a good rule of thumb is to pack comfortable clothing that you can layer. Loose-fitting clothing in breathable fabrics will keep you cool in warmer weather, while a light jacket or cardigan will come in handy for cooler days or evenings. And if you plan on doing any sightseeing, be sure to wear comfortable shoes. Nothing like a nasty blister to ruin a good vacation, right?

In just a second, I'll share my specific recommendations for exactly what to wear in Windsor in fall—whether you're visiting the Windsor Castle, going on a boat tour of the Windsor-Detroit Riverfront, exploring the Art Gallery of Windsor, or visiting the Detroit Zoo.

🔗 What should women wear in Windsor, Ontario in fall?

Windsor in fall is generally mild, and there are a few key items you'll want to pack. Here's what I definitely wouldn't go without: stylish hat, comfortable flats or loafers, denim jacket, pashmina, and jeans. With these essentials, you’ll be all set to experience everything Windsor has to offer.

🔗 Stylish hat

A good hat can be the difference between a great Windsor trip and a terrible one. Not only do hats help you look your best in photos, but they also make you feel more confident and put-together as you explore, adding a touch of style to any outfit. To choose the right hat, consider both function and fashion. A wide-brimmed straw hat is perfect for protecting your face from the sun (a good idea in all weather!) while a trilby is ideal for nights out on the town. No matter what your plans are in Windsor, just know there's a hat for the occasion.

Here are some options I'd recommend:

🔗 Comfortable flats or loafers

Packing the right shoes for Windsor can make the difference between a comfortable trip and a difficult one. While there are many factors to consider when packing your shoes, comfort is always the most important. Flats or loafers are a great option for travel, as they can be easily slipped on and off at security checkpoints and are generally super comfortable to walk in.

If you're stuck for ideas, here are some of my favorites:

🔗 Denim jacket

A denim jacket is great to have in Windsor. They are stylish and can be dressed up or down, making them perfect for any occasion. Denim jackets are also very versatile. They can be worn over a dress for a night out or with jeans and a t-shirt for a casual day exploring. Best of all, denim jackets are lightweight and easy to pack, making them ideal for travel. When choosing a denim jacket for Windsor, look for one that is comfortable and flattering. A classic denim jacket will never go out of style and can be worn year after year. For a more unique look, try a distressed denim jacket or one with embellishments such as embroidery or beads.

These would be perfect:

🔗 Pashmina

A pashmina is a must-have accessory for a trip to Windsor. They can be used as a scarf, sarong, blanket, or even a headscarf. They are light and easy to pack, yet they provide warmth and color to any outfit. Pashminas come in a variety of colors and patterns, so it's easy to find one that compliments your personal style. When choosing a pashmina, look for one that is made from natural fibers such as wool or cashmere. These fibers are not only more durable, but they will also breathe better and keep you covered without making you sweat.

Here are some of my favorites:

🔗 Jeans

You just cannot go wrong with a good pair of jeans. They're comfortable, versatile, and easy to care for—not to mention they always look great. Whatever you're doing in Windsor, jeans will always come in handy. Of course, not all jeans are created equal. Be sure to choose a pair that's comfortable and flattering. If you'll be doing a lot of walking, look for a light-weight denim that won't weigh you down. And if you're hoping to dress up for a nice dinner out, a dark wash denim will always do the trick.

Here's a few ideas to get you started:

🔗 What should men wear in Windsor, Ontario in fall?

For guys, here's the list of essentials I recommend you start with: jeans, sneakers or loafers, sweaters, collared shirts, and light jacket. With these in your suitcase, I guarantee you will enjoy your trip to Windsor in comfort and style.

🔗 Jeans

You just cannot go wrong with a good pair of jeans. They're comfortable, versatile, and easy to care for—not to mention they always look great. Whatever you're doing in Windsor, jeans will always come in handy. Of course, not all jeans are created equal. Be sure to choose a pair that's comfortable and flattering. If you'll be doing a lot of walking, look for a light-weight denim that won't weigh you down. And if you're hoping to dress up for a nice dinner out, a dark wash denim will always do the trick.

Don't have anything suitable? Grab one of these:

🔗 Sneakers or loafers

Sneakers or loafers are essential for visiting Windsor. They're comfortable, versatile, and easy to pack. And, when you're on your feet all day, they can help prevent aches and pains. But how do you know which sneakers or loafers to pack? If you'll be doing a lot of walking, opt for a sneaker with good arch support and cushioning. And don't forget style! Sneakers and loafers come in countless colors and designs, so pick something that goes with the rest of your outfits.

These are some of my favorites:

🔗 Sweaters

Sweaters are super versatile and can be dressed up or down, making them ideal for both day and evening wear in Windsor. They also take up less space than other types of warm clothing, so you can pack more sweaters into your suitcase without sacrificing style. When choosing sweaters for travel, look for ones that are made of wrinkle-resistant fabric, such as Merino wool or cashmere. These materials will help to keep you warm without adding bulk.

Here are a few of my top picks:

🔗 Collared shirts

A lot of people think that collared shirts are only for work, but they can actually be really handy when traveling too. For one thing, they can help you dress up if you need to go someplace nice for dinner or a show. But how can you tell which collared shirts are worth packing? You can never go wrong with ones that are made from light, breathable fabrics like cotton or linen.

Here's a few ideas to get you started:

🔗 Light jacket

A light jacket is always a good idea to pack for Windsor, even if the weather is forecast to be warm. You never know when the weather will change or you'll end up in an air-conditioned place. They're also useful for protection from the sun and wind. And of course, it can get chilly in the evenings. But not all light jackets are created equal. For example, denim jackets are great for everyday wear but they're not always packable because they can be bulky. A better option is something like a nylon windbreaker which can be rolled up into a small bundle.

These would be perfect:

I hope these recommendations for what to wear in Windsor, Ontario will help make your fall visit unforgettable. Now that you have a better idea of what clothing to take, it's time to pack your suitcase—and then go ahead and enjoy everything Windsor has to offer!