Chesapeake, Virginia in Winter: What to Wear

Got a winter trip planned to Chesapeake, VA? Chesapeake can be fun to visit in the winter, but you'll want to make sure you're dressed right. The weather is cool and dry, with temperatures averaging around 52°F (that's 11°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 Chesapeake, 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 Chesapeake in winter—whether you're crabbing in the Chesapeake Bay, visiting the Norfolk Botanical Garden, exploring the Dismal Swamp National Wildlife Refuge, or visiting the Virginia Zoo.

🔗 What should women wear in Chesapeake, Virginia in winter?

Chesapeake in winter is generally cool, and there are a few key items you'll want to pack. Here's what I definitely wouldn't go without: sweaters, warm coat, comfortable flats or loafers, stylish hat, and pashmina. With these essentials, you’ll be all set to experience everything Chesapeake has to offer.

🔗 Sweaters

Sweaters are super versatile and can be dressed up or down, making them ideal for both day and evening wear in Chesapeake. 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 some options I'd recommend:

🔗 Warm coat

A good coat will keep you warm in inclement weather and can also be a stylish addition to your travel wardrobe. When choosing a coat, look for one that is made from insulating materials such as wool or down (or synthetic equivalents). A hood is also a helpful feature, as it will protect your head and face from the elements. If you plan on doing any outdoor activities, such as hiking or skiing, make sure to choose a coat that is waterproof and windproof.

Here are a few of my top picks:

🔗 Comfortable flats or loafers

Packing the right shoes for Chesapeake 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.

Here are a few of my top picks:

🔗 Stylish hat

A good hat can be the difference between a great Chesapeake 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 Chesapeake, just know there's a hat for the occasion.

I found these which would all work great:

🔗 Pashmina

A pashmina is a must-have accessory for a trip to Chesapeake. 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.

These are some of my favorites:

🔗 What should men wear in Chesapeake, Virginia in winter?

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

🔗 Stylish hat

A good hat can be the difference between a great Chesapeake 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 Chesapeake, just know there's a hat for the occasion.

Any of these should work:

🔗 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.

These 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 Chesapeake, 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.

I found these which would all work great:

🔗 Light jacket

A light jacket is always a good idea to pack for Chesapeake, 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 options are both stylish and comfy:

🔗 Sneakers or loafers

Sneakers or loafers are essential for visiting Chesapeake. 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.

I found these which would all work great:

I hope these recommendations for what to wear in Chesapeake, Virginia will help make your winter 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 Chesapeake has to offer!