What to Wear in Chesapeake, Virginia This Fall

Got a fall trip planned to Chesapeake, VA? Chesapeake can be fun to visit in the fall, but you'll want to make sure you're dressed right. The weather is warm and dry, with temperatures averaging around 71°F (that's 22°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 fall—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 fall?

Chesapeake in fall is generally warm, and there are a few key items you'll want to pack. Here's what I definitely wouldn't go without: denim jacket, sandals, stylish hat, loose-fitting clothing, and jeans. With these essentials, you’ll be all set to experience everything Chesapeake has to offer.

🔗 Denim jacket

A denim jacket is great to have in Chesapeake. 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 Chesapeake, 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 are some of my favorites:

🔗 Sandals

While many people think of sandals as nothing more than summertime shoes, they can actually be a versatile and practical option for year-round travel to warmer destinations. For one thing, they're comfortable and easy to wear, which is ideal for exploring Chesapeake. They also offer good ventilation, which is important in hot weather. Just bear in mind that sandals should provide good support for your feet and ankles, which you need to help to prevent injuries.

Any of these should work:

🔗 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.

Need some inspiration? Start here:

🔗 Loose-fitting clothing

When packing for Chesapeake in fall, it's important to choose clothing that will keep you cool and comfortable. Loose-fitting clothes are ideal, as they allow air to circulate around your body and help to regulate your temperature. Look for lightweight fabrics such as cotton or linen, which will help you to stay cool even in the hottest weather. When choosing colors, stick to light shades which will reflect rather than absorb heat. And don't forget to pack a few items that can be mixed and matched to create different looks. With a little planning, you can ensure that you'll be comfortable and stylish no matter what the weather is like on your trip.

Here's a few ideas to get you started:

🔗 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.

Here are some options I'd recommend:

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

For guys, here's the list of essentials I recommend you start with: lightweight pants, button-down shirts or polos, shorts, sneakers or loafers, and loose-fitting clothing. With these in your suitcase, I guarantee you will enjoy your trip to Chesapeake in comfort and style.

🔗 Lightweight pants

If you're planning a trip to Chesapeake that involves any sort of physical activity—hiking, climbing, biking, etc.—you'll want to pack a pair or two of lightweight pants. They're much more comfortable than jeans or khakis when you're sweating, and they'll dry much faster if you get caught in a rain shower. You can also roll them up and stuff them into your backpack or suitcase without taking up too much space.

Any of these should work:

🔗 Button-down shirts or polos

Button-down shirts or polos are always a good idea to pack. They don't wrinkle easily and can be dressed up or down depending on the occasion. They're also perfect for layering when the weather gets cooler at night. Pick ones that are comfortable and breathable, and ideally lightweight too. It's also a good idea to choose neutral colors like white, black, or blue as they can be easily teamed with other pieces in your wardrobe.

Need some inspiration? Start here:

🔗 Shorts

Shorts are one of the most versatile and essential items in any travel wardrobe. They can be dressed up or down, depending on the occasion, and they're perfect for dealing with hot weather. Plus, they're easy to pack and don't take up much space in your suitcase. Just make sure to pack a few different colors and styles so you'll have something to wear for different occasions.

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

🔗 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.

Here's a few ideas to get you started:

🔗 Loose-fitting clothing

When packing for Chesapeake in fall, it's important to choose clothing that will keep you cool and comfortable. Loose-fitting clothes are ideal, as they allow air to circulate around your body and help to regulate your temperature. Look for lightweight fabrics such as cotton or linen, which will help you to stay cool even in the hottest weather. When choosing colors, stick to light shades which will reflect rather than absorb heat. And don't forget to pack a few items that can be mixed and matched to create different looks. With a little planning, you can ensure that you'll be comfortable and stylish no matter what the weather is like on your trip.

Here are some of my favorites:

I hope these recommendations for what to wear in Chesapeake, Virginia 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 Chesapeake has to offer!