A Hiking Date Can Be Adventurous, Fun, & Romantic

Since a hiking date can mean so many awesome things, it also means being prepared for anything. So what to wear on a hiking date becomes an important decision for many different reasons.  

After all, you aren’t just going to your favorite restaurant. You are going to be showing off your outdoor skills while getting to know someone at the same time. A hiking date also provides the opportunity for conversation, physical activity, and enjoying nature. So being ready with just the right wardrobe makes a good first date even better.

Reasons to Go on a Hiking Date

  • New date night idea
  • Romantic time alone
  • Get to know someone better
  • Break from the restaurant scene
  • Group date to meet new people
  • Celebrate a special occasion
  • Show a new side of yourself
  • Marriage proposal opportunity

Different Kinds of Hiking Dates

Just as there are many different levels of hikers, there are many different kinds of hiking dates. For example, there are fascinating walking tours of larger cities, which make for a perfect first date. There are also guided nature tours for hikers of local parks. 

This is where beginning hikers can learn about the natural features of the area in a group setting. These are easy walks for new hikers, and casual wear like a t-shirt and leggings are welcome. There are no hiking boots required for this kind of hiking date.   

Pro Hiking Date Tip

Reach out to the local Parks & Recreation Department for local guided tours of the area for novice hikers. You may be surprised at what they have to offer. 

A Hiking Date as a First Date

Asking someone to hike with you alone on a first date might not be a good idea. Especially if you are going out to a remote location by yourselves. Nevertheless, you can ask someone to be part of a group of hikers who are going to that same place. Once this hiking date goes well, ask them to go on another. This time, just the two of you.

Places to Go on a Hiking Date

  • City, State, or National Park
  • Historical Walking Tour 
  • Nature Hiking Tour
  • Beginning Rock Climbing
  • Ski Resort (summertime)
  • Local Lake Trails
  • City/County Walking Trails

Picking an Actual Location 

The location of the trail you pick will decide what you should wear. The trail should be easy to get to and less than an hour away. If the date doesn’t go well, you don’t want a long, silent car ride back. 

Keep in mind that as with any date the, the first hiking date rule applies. Anything that can go wrong will. So as with any outdoor activity, have a back-up plan. Make sure there are indoor activities to do in the area, just in case it rains. Also, call ahead that day to make sure the trail is open. Mother Nature is unpredictable and trails shut down for different reasons on a moment’s notice. 

Pro Hiking Date Tip

Always hike the trail yourself first so that you can be knowledgeable on your hiking date. You don’t want to get your date lost out in the wilderness. You also want to make sure that you can complete the trail yourself without being exhausted. It doesn’t look good when you suggest a trail for a hiking date that you can’t finish. 

Keep in mind, this isn’t a physical endurance test. This is a date to enjoy another person’s company. A person you want to see again, hopefully. So make your hiking date fun, interesting, and above all, enjoyable!

What to Wear on a Hiking Date Broken Down

Now that you’ve picked the location for your hiking date, you will know better what to wear. This is especially true if you have walked the trail yourself. Keep in mind, your date may have never hiked before. They are relying on you to tell them what to wear. 

This is the time to score some big points with your date before you even set foot on the trail. Ask about what they already have in their closet. If they don’t have hiking boots or leggings, they may be a hiking novice. 

Most people will overstate things like their hiking experience because that’s what they do on a first date. A first date is like a job interview. You don’t exactly lie, but you do enhance your abilities and interests. So if someone doesn’t know what a moisture-wicking t-shirt is, chances are, they have no hiking experience. 

Make sure you pick a location where your date can excel. You may not get a second chance if you pick a trail they weren’t ready for. Or dressed right to handle. Conversely, you can score big points on a first date if someone knows they can trust you.

So, as you can see, a hiking date will present many different wardrobe challenges. This is because you are making many different impressions at once:

  • How you dress for a specific activity
  • Your sense of direction
  • How you plan ahead for a date
  • How you consider someone’s feelings
  • How you handle an unpredictable situation
  • How athletic you are
  • What you talk about one-on-one

So let’s look at how to look your best while being comfortable and practical on a hiking date.

Do You Have to Wear Hiking Boots?

If you don’t own any hiking boots, don’t go out and buy them just for a hiking date. Unless you have time to break them in, you will be sorry at the end of the day. You will have many blisters to smile through as you pretend to be a seasoned hiker. 

The main reason people buy hiking boots is because of ankle support. This is because it’s easy to twist your ankles on rough terrain. The ankle support of hiking boots helps prevent this. As well, hiking boots are sturdy, close-toed footwear that protects your feet from lots of injury on the trail. But if you don’t have hiking boots, don’t worry. 

Trail runners, hiking shoes, or running shoes will work just as well. Just make sure they will protect your feet from rocks and debris you may encounter on the trail. They should also keep your feet dry and have a good grip like hiking boots would. Wearing shoes with rubber soles and deep treads are acceptable substitutes for hiking boots. Just use common sense and don’t wear your Chaco’s unless you are a seasoned hiker.  

Pro Hiking Date Tip

Many newbie hikers show up on the trail with brand-new hiking boots to look like they belong. Then they quickly realize all the real hikers are wearing running shoes. Don’t be this person trying to fit in. Be yourself instead and you will have a much better time on your hiking date.  

So besides hiking boots, let’s look at what you may already have in your closet:

  • Sturdy, worn-in, supportive athletic shoes
  • Nylon/Lycra blend, breathable socks
  • Pants with some stretch
  • A t-shirt with a little personality
  • A trendy seater
  • A light water-repellent jacket
  • A hat with a brim for shade

As long as your outfit is sensible for hiking – and stylish for a date, you’ll be fine.

What Kind of a T-Shirt Should Hikers Wear?

Hikers on any kind of hiking date should wear a t-shirt (and other clothing) made of moisture-wicking material. So a t-shirt should definitely function to wick sweat in case you get hot while hiking. It should also stretch with your movements and repel dust and moisture at the same time.

This sounds like a tall order, but many clothing companies make this kind of t-shirt. (A moisture-wicking t-shirt may also be called a quick-drying t-shirt.) Chances are, if you have a t-shirt you work out in, it is a t-shirt to go hiking in.

You can get a moisture-wicking t-shirt like this in any department store. They are smart-looking, fashionable, and will keep you sweat-free for your hiking date.

Pro Hiking Date Tip

Never wear anything cotton on a hiking date. Cotton absorbs and then retains moisture, taking forever to dry. As well, a light-colored cotton t-shirt will highlight your armpit sweat. Having pit stains is the worst impression you can make on a first date.  

What Kind of Pants or Shorts Should Hikers Wear?

Lightweight, flexible, cargo pants that go with a t-shirt are the best thing to wear on the trail. Make sure that your cargo pants are not 100% cotton, though. You will still want cargo pants/shorts made of moisture-wicking material. 

Lightweight, moisture-wicking pants keep you cool. As well, if you sit down on the trail – you may accidentally sit in water. (It’s that first date law of anything that can go wrong, will.) And you don’t want the seat of your pants wet for the rest of your hiking date.

You may also happen to splash through a stream on purpose. Or, if there hasn’t been rain for a while, you may encounter a lot of dust. So you want to wear pants that will dry quickly and that you can easily brush the dirt off of. If you are hiking in the winter through the snow, you definitely want moisture-wicking pants. 

Say Yes to Leggings, Yoga Pants, and Running Tights

Women hikers can take advantage of the fact that leggings and yoga pants are perfect for hiking dates. They stretch, wick moisture, and are made for moving. They are also perfect for a first date outfit. The best thing about really cute leggings and yoga pants is that they are probably already in your closet. 

If not, it’s the perfect time to go shopping for new leggings to go with a new t-shirt. This is a purchase that will help get you excited about your hiking date! Plus, leggings can be worn again for something else. 

Pro Hiking Date Tip

Never wear jeans on a hiking date. Jeans are the worst article of clothing for hikers to wear, period. Even in the winter, jeans are heavy – but they do not keep you warm. Although, jeans will make you feel even hotter on a warm day. Jeans also have no stretch, and if you get jeans wet they will never dry. It’s better to stick with cargo pants, shorts, or leggings for better comfort and style.  

Other First Date Considerations for Hikers

You should always dress in layers. A short-sleeve t-shirt or tank-top under a long sleeve t-shirt is the best. This way, you have a warm shirt for colder morning or evenings. Then you can just take it off and tie it around your waist if it gets too hot. If it is especially chilly, you can also wear leggings under hiking pants.

If you are hiking in the winter, you will need a coat, hat, and gloves. Even in the summer months, it is still wise to take a light, water repellent jacket in case it rains. 

A Backpack for Each of the Hikers Is Especially Helpful

Here are some of the things you can put in it:

  • Sunglasses
  • Sunscreen
  • Insect Repellant
  • Cushy sleeping pad or blanket
  • Snacks
  • Thermos for hot or cold drinks 
  • Rain Poncho
  • Baseball caps or sunhats
  • Flashlights or headlamps

Pro Hiking Date Tip

Always prepare for the weather. This is why you should wear more than one t-shirt, along with hiking boots or running shoes with rubber soles. You certainly want to be prepared to get out of the rain if it comes unexpectedly. You also want to be warm the entire time you are on your hiking date. 

If you go out in bad weather, you aren’t going to make a good impression on a first date. Again, it’s just common sense to check the weather report first and make other plans. 

A Final Hiking Date Pro Tip: You Can Always Talk About the Weather

The great thing about a hiking date is that you can talk about the weather, trees, the trail, the beauty of nature, etc. And since there are so many nature-things to notice, comfortable silences are good as well. Don’t ever feel like you need endless chatter to fill the gaps in a conversation. Let the sounds of nature do it for you. That’s the real beauty of a hiking date. 

Sam Brooks

Sam Brooks

Hi, my name is Sam Brooks and I'm a huge hiking, fishing and camping enthusiast. I bring my dog Max as often as I can because he also loves the great outdoors. Although I consider myself a private person, I really want to share my passion and knowledge with the readers here at outdoorcommand.com