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Congratulations! You’ve got yourself a hiking date! They can be some of the most enjoyable and memorable dates ever! But do you know what to wear on a hiking date? Sure you want to look great on your date, but weather, terrain, and safety factor into the equation too.

Are you new to hiking? Maybe you’ve been hiking a long time and have a bunch of hiking clothes to pick from. Whichever the case, we’ll cover what you need on your hiking date.

Let’s look at some of the necessary clothing and gear you’ll need for having a safe and enjoyable hiking date while still looking cute. After all, we want this to lead to something more than just hiking buddies.

What To Wear On A Hiking Date Varies with Weather and Seasons

A couple enjoying a mountain trail on a hiking date.

Dress for the Season: I’m not telling you anything new. Dress for the season. If it’s Winter, you’re going to need a coat, hat, gloves, hiking boots, and possibly more like thermal underwear or microspikes for your boots.

Check the Weather: Check the weather on the days before your hike and at the trailhead to make sure you’re dressed accordingly.

Dress in Layers: The temperature will change throughout the day and with significant elevation change. You’ll also want the option to remove or add layers depending on these temperatures and your body’s temperature changes due to physical exertion.

Remember Bug Spray: At different times of the year, you’ll need to wear bug spray to cut down on bug bites and the nasty diseases that some of these can cause like Lyme disease or the Zika virus. I know you might be focused on your outfit but bug spray is no less important. You don’t want to end your hiking date looking like you have Chickenpox or be in need of a tick check by your date.

Wear Sun Protection: Sun protection is often thought of as lotion but certain clothes have UV protection as well. Consider the combination of sunscreen and clothing with built-in UV protection to protect your skin from sun damage.

What To Wear On A Hiking Date Varies with the Chosen Trail

A couple on a hiking along a mountain ridge trail.

Firstly, if you or your date are new to hiking, pick an easier trail that doesn’t have a lot of hills. Gasping for breath on a hiking trail does not allow for conversation and you want to learn more about your date. There are plenty of easy trails that lead to gorgeous views… Waterfall hikes can be a great choice.

Talk over the hike with your date. Knowing what to wear and carry on a hiking date will greatly depend on the difficulty level of the hike, terrain, elevation, and condition of the trail… Has it rained recently making the trail muddy? Will you want trekking poles for stability and to protect your knees on uneven terrain?

Hiking Footwear

Don’t ever hike in flip-flops or sandals. Certain sneakers may be acceptable on easier hikes but you’ll want hiking boots for ankle support, stability, and traction on most trails. If you buy new hiking boots for your hike, make sure to get a waterproof pair and break in your boots beforehand or you’ll end up with some nasty blisters.

Looking for a great hiking boot? My boot of choice is Vasque. I’ve exclusively hiked in Vasque hiking boots since 2006.

Dress in Layers

As mentioned in the weather section, you want to dress in layers. Being able to easily add or remove layers is important when you’re on a long hike or a trail that changes in elevation or difficulty due to terrain.


Many women wonder if you can hike in leggings. You can! The trend for wearing compression leggings for hiking is on the rise but they aren’t right for every trail. They aren’t the best for long-distance hikes, hikes with higher technical difficulty, or trails that aren’t well-manicured. Brush and briars can grab hold and pull many fabrics.

If you hike in leggings…

  • Avoid long multi-day hikes. They can get funky and cause an infection.
  • Make sure to get a pair suitable for hiking.
  • You want a pair that has seam placement that won’t chafe.
  • You want a fabric that wicks moisture and dries quickly.

Don’t Wear 100% Cotton

Your outfit should be suitable for the hike length and difficulty. A cotton t-shirt may be fine on a comfortable Spring or Fall day on an easy trail where you aren’t likely to sweat much, but polyester dries faster and won’t absorb as many body odors. If you don’t want to smell like a high school gym locker after your date, look for moisture-wicking clothing.

Wool socks are great in every season for keeping your feet dry and comfortable.

No Jeans

Wearing jeans is one of the beginner hiking mistakes you want to avoid. I love my jeans but jeans are terrible for hiking.

  • Most jeans are cotton.
  • They can cause serious chafing.
  • They don’t dry quickly when they get wet.
  • Water-soaked jeans can cause you to lose heat in cold weather and can even ice up in freezing temperatures.

Hiking Gear for Hiking Dates

A couple walking along a trail on their hiking date.

Hiking dates will often require more than just hiking clothes. There are hiking essentials you’ll need for safety and comfort.

  • Hydration backpack with plenty of water. These packs have room for your gear and keep you from having to carry a water bottle. You want your hands free especially if you’re using trekking poles.
  • You or your hiking date need to carry a first-aid kit.
  • Food and snacks for the trail and possibly a romantic picnic.
  • Clothing layers can easily be stored away in your hydration pack.
  • Sun protection.
  • Bug protection.
  • Your phone in case of an emergency.
  • You need a map of the trail. You don’t want to get lost.
  • A compass in case you do get lost. Make sure you learn how to use it before your hike.
  • Download a GPS app on your phone or invest in some other GPS tool like a Garmin.
  • Portable power banks are handy for those times when your phone runs out of juice.
  • A headlamp in case it gets dark before you’re off the trail.
  • Trekking poles are great for balance and stability. Especially if you’re on uneven terrain.
  • Multi-tools are great gadgets in emergency situations or for general repair needs.
  • A garbage bag to store your trash.
  • Disposable poncho in handy in case of unexpected rain.

Your Hiking Date Outfit

A romantic couple sitting on a rock enjoying the a lake view with mountains in the distance.

So exactly what should you wear? Hiking boots, long pants, shorts, convertible pants, leggings, a polyester t-shirt, flannel…?

What you wear will vary greatly according to your personal taste. Some people like looking rugged, some are gearheads, and some just want to look the part or look cute.

Communication helps greatly. Especially if you’re new to hiking. Ever shown up for a date and been over or underdressed?

Can you think of a hiking outfit that might catch the eye of your date?

I went on hiking dates with my wife before we got married. Our dates were around Nashville, TN in the Spring, Summer, and Fall. Our typical hiking outfits were hiking pants or shorts, t-shirts, baseball caps, hiking boots, and waterproof jackets that were often stored away in our hydration backpacks with the other hiking gear I mentioned. What we wore on our hiking dates while single and after marriage remains roughly the same. Pretty simple.

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A couple on a hiking date enjoying an impressive view at the edge of a canyon. Text says... What to Wear on a Hiking Date.
Steve Hood

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One Comment

  1. Great post! I completely agree, it’s so important to dress comfortably and practically when going on a hiking date. I always make sure to wear breathable fabrics, sturdy hiking boots, and layers for added warmth. It’s also a good idea to bring a lightweight waterproof jacket or poncho in case of unexpected rain showers. Thanks for sharing these valuable tips!