A trail marker begins a trail into the forest.

What to Wear on a Hiking Date | Guide for Men and Women

Last updated on April 14th, 2021 at 04:50 pm

Here you are, you’ve found yourself with weekend plans. You and your special someone are meeting at a specific trail marker and you don’t know what to wear on a hiking date. Maybe you’re planning a journey with someone you’ve only just met, or possibly you’ve made past poor wardrobe decisions.  Either way, it’s a date.  Now, you’re worried to overdress for the occasion, but you definitely don’t want to throw on pilled-up sweats and appear uninterested. 

Whether you’re getting ready for a long or a short hike, both men and women should take into consideration weather and even fabric choices for a hiking date. The right outfit should make you feel confident before heading to your adventure date.  Preparation will give you the self-assurance needed to conquer this dating experience and your hiking route. 

Hiking dates are a great way to get to know one another, and to continue so through future trails. Once you’ve read through a few of our suggestions below, you’ll be well on your way to bravely saying ‘yes’ to any route in any season with that special someone. We’ve compiled some recommendations below that are very useful in preparing for hiking dates. 

Different Seasons Require Different Hiking Gear for Dating

Opportunities in the great outdoors are limitless, but don’t be frightened by the possibilities.  Small and manageable considerations can be completely life-changing. We were born to traverse the Earth with other people, it’s as natural as anything else, even while pregnant. 

RELATED: How to Pick Hiking Boots | Choose The Right Pair

Whether you’re heading out in the dead of winter, or braving summer humidity, consider the elements when planning.  Layering or packing away a few essential wardrobe items in a back pack can be the perfect compromise.  

Spring Outfits and Considerations

Spring is a time for the birds and the bees.. and also the mud, rain and wet terrain.  Don’t let marshy trails and unexpected cold temperatures sneak up on you.

While hiking in cold spring weather, for both men and women, we suggest pants that are moisture-wicking and quick-drying. 

Pullovers or light jackets layered over an athletic shirt is a good go-to look for Spring. Jackets can be tied around the waist or stuffed into a back pack (next to your emergency lightweight rain jacket if you’ve got one).

Waterproof running shoes are perfect for wet spring elements. If you don’t have a pair of shoes that can handle the trail, check out our post on The Best Speed Hiking Shoes where we outline some SUPER comfortable (and stylish) trail shoes.

Regardless of what shoe you wear it is very important it is comfortable. The last thing you want is to have to turn back early because of a blister.

PRO TIP: I always bring an extra pair of socks [and a bag for the soggy ones] in case I’m defeated early on by puddles.

Women Wear for Spring Hikes

As a woman, I love high-waisted athletic pants that cover my behind. They give me the confidence I need while climbing stairs or traversing elevated terrain. Fortunately, many of the options out there for active use are also very attractive. Any of the pants I wrote about in this post would work perfectly on a hiking date. 

Dress in layers to keep yourself happy and relaxed on your journey.

Style can also be an interesting talking point. Spring is the time for color and flowers, don’t be afraid to show your personality in your dating wardrobe! 

Men's Wear for Spring Hikes

For men, a pair of nylon hiking pants that feature a bit of stretch will be perfect for your date. If you’re comfortable, you’ll be confident.

Dressing in layers is equally as important for men as it is for women. Remember to wear warm enough outerwear that you can handle colder temperatures than you expect. The last thing you want on your date is to be the cold/underprepared one. 

Remember, if you layer correctly, you can always shed the layer to get in your temperature zone. 

 

 
 
 
 
 
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Summer Hiking Outfit Suggestions and Prep

Trekking into the wild during Summer presents it’s own set of challenges. Whether you’re heading out for a sunrise hike or hitting the trails when the sun is highest in the sky, you’ll have to prepare for different summer issues.

Don't Let Summer Bugs Ruin Your Date

Summer and humidity bring loads of insects that you’re sure to encounter on the hike.  Apply all-natural bug repellent beforehand or wear long sleeves and pants of lightweight material (or both). You don’t want to be swatting away bugs while getting to know your date.

If you don’t have any natural bug spray, I really like a plant-based lemon and eucalyptus repellent. I find they work really well. You can read more about my favorite plant-based insect repellent on Amazon here: REPEL Lemon Eucalyptus Insect Repellent

Sun Protection is VERY Important

You will, however, want to protect yourself from the heat and from the sun during this season. Some active-wear is made with sun-protective properties as well.

Summer specific garments play double duty during the summer months as both protection for bugs and UVA/B rays. Shirts and pants with UPF ratings can provide comfort while keeping greasy sunscreen and repellents away from your dating scene.   

Cotton bandannas are perfect for emergency perspiration situations (and potential hay fever breakdowns).  Bandannas are very useful and versatile during summer hikes.  They can be tied around your neck or as a headband to absorb excess sweat.  Fearlessly wipe perspiration from your brow or upper lip and continue believing this isn’t the most difficult uphill climb ever. 

A baseball cap can help protect your face from exhausting summer sun as well. When trying to hold the attention of your date, squinting into the sun can be a little less than ideal. 

A Few Things NOT to Wear on a Summer Hike

Leave the screen-print cotton tees and denim at home during summer hikes.  Cotton absorbs and holds sweat that can pool into underarm and back patches.  To avoid feeling less than confident, opt for lycra, elastine, spandex and nylon materials for your entire outfit.  

 

 
 
 
 
 
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Fall Hiking Date Wardrobes

Breathtaking views and picturesque autumn colors await you during a fall hike. Depending on the weather it could be perfectly warm and crisp.  Or, which is more likely, falling leaves have poked holes in the tree coverage and made way for cold fall winds.

For Fall, you’ll find a lot of values in layers. Moisture-wicking materials like spandex-jersey knits under an active vest or wind-breaking jacket are the perfect combination of style and function.  You’ll stay warm and have ample options during the entire hike.

After experiencing a few mid-hike debacles, we always pack away an emergency, lightweight and waterproof jacket in case the skies open up.

Pillowed vests, ear protection and a light pair of gloves could provide useful while hiking throughout the day for both men and for women.

For footwear, we suggest a pair of hiking boots for tough or slippery terrain. You’ll benefit from boots with lugs that grip the ground.  Leaves can be slick and loose or trails become wet unexpectedly during this time of year. If you aren’t sure how to pick a good pair of boots, have no fear, we wrote an extremely detailed post about how to select the perfect pair of boots.

Whatever the outfit, dress comfortably to enjoy the beautiful changing fall colors without chilly distractions.

 

 
 
 
 
 
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Winter Hiking Outfit Ideas

Winter is a great time to head outdoors. The trails will be sparsely occupied and you’ll have plenty of privacy to laugh loudly, joke, and maybe create some snow angels.  

You’ll absolutely need a winter coat that protects you from the wind. On those weirdly warm days, however, a water-repellent down vest over a long sleeve shirt could be a perfect combination. 

Large hoods can hinder conversation and your ability to hear your partner. For both men and women, we suggest a headband, ear-warmers or a knit hat to keep the conversation flowing. 

Comfort and warmth should always be paramount to style. A warm pair of water-resistant gloves and a hat can always be removed to prevent overheating mid-journey. If you don’t bring them though… you will likely regret it.

Footwear is particularly important during this season. Water-proof hiking boots with high ankle coverage are a sound investment for winter hikes.  

If you know your date will occur on flat, stable terrain casual winter boots will work okay in a pinch. When in doubt, or if unsure where the day may lead, your best bet is water-proof footwear made to grip the trails. 

Consider also, the treachery of our bodies in these times of seclusion and intimacy. With cold weather and outdoor exercise comes the dreaded runny nose. For this, I always pack tons of tissues. This is especially important if hiking with someone for the first time. 

However, you can also wear a light scarf to hide your face from the elements while listening to your partner.  Keeping your face hidden incrementally will help your airways maintain proper humidity to avoid the overproduction of mucus. This is my secret weapon against my runny nose!

Keep in mind your partner will also be struggling, it’s best to just make light of it, things will be ok. 

 

 
 
 
 
 
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Some Fabrics May Be Best on a Hiking Date

From your head to your underwear, avoid cotton at all cost for maximum comfort and breathability during activity. Cotton absorbs and holds moisture, making anywhere it touches either humid or bone-chillingly cold. 

Denim (made from cotton), regardless of the amount of spandex, will also retain heat and excess moisture.  It’s always best to hike in materials made for the trip.  By not following this advice, I have made this mistake many times.  I’ve hiked in supreme comfort for about a mile, only to desperately peel off sweat-laden skinny jeans while my partner plays lookout.

Performance materials like nylon-spandex blends are made to be used during athletic activity for a reason. Choose hiking gear that notes its breathability, or is made from these synthetic blends to avoid becoming a sweaty mess on the trails.  

For men, loose fitting hiking pants or running shorts made from similar materials are perfectly amazing for hikes. Just be sure to leave the cotton jockeys at home and instead opt for poly-spandex and elastine, breathable undergarments.

What You Wear on the Date Should Make You Feel Confident

Our best and most valuable piece of advice is to be yourself. Dress comfortably and be open to anything. It’s so attractive to be humble and not in denial about how cold or wet you really are. 

Confidence is sexy, this goes for men and women both. So, embrace all of your decisions and be prepared to rock anything that makes you comfortable enough to say ‘yes‘ to that extra 3 mile loop.

Preparing a Small Pack of Extras

A great way to prepare for your hike and also impress your date is by packing a small backpack with emergency essentials or food to share. 

I can’t tell you how many times I’ve really needed eye drops during dog-wood season and my partner pulled through. It’s the best feeling to have something that your hiking date may need. 

If you are wanting to bring something that can hold some essentials you should check out our post on the best lightweight fanny packs for hiking

What I Deem as Emergency Items To Impress

  • drinking water
  • aspirin
  • eye drops
  • sunglasses
  • tissues
  • small travel bottle of ibuprofen
  • tissues (yes, twice)
  • extra hair ties
  • natural bug spray
  • hand-sanitizer
  • $20 emergency cash
  • 2-4 bandaids
  • cotton bandana
  • emergency trail bar, bring two to share!

Bring Something Fun

During your hike, bringing a treat or talking point could be a great way to share a unique experience with your date.  Whether it’s a homemade trail-mix, a set of binoculars, or a planned picnic, special add-ons will always go a long way.  

This is the beauty of hiking dates, you can pull all kinds of weird stuff from your bag and it is almost always well received. Just make sure you know beforehand if your date is vegan before unpacking a huge bag of super-niche flavored beef jerky bits.

Get Gear, Share Your Pics, And Get Dating

Publicly your dating profile should tell to the world who you really are. The right gear and confidence in your photos shouts to all potential suitors that you’re looking for a match who’s ready for activity. That what you want in a potential mate is adventure and you’ve already got your bags packed. 

If you’ve met your date through this type of outlet, finding what to wear on your hiking date could be as easy as mirroring their choices.  You can tell a lot about what to expect on your date by gauging their knowledge and skill level through profile pictures.

Whether you’re the one doing the asking or the recipient of an invitation, hiking dates are fun.  They’re a unique and intimate way to learn about one another while doing something active. 

Finding new and interesting experiences for date destinations can be stressful, but the trails are always there for you. While dinner and drinks afford comfort and familiarity, a possible connection can get lost on a sea of noise. 

So, donning the right gear for the season, ditch those loud overcrowded venues. Instead, head out into nature for good conversation and an incredible shared experience.  

Image Credit: Coconino National Forest | (https://www.flickr.com/photos/148456610@N03/) | CC0 1.0 Universal (CC0 1.0) Public Domain Dedication –reduced file size and image

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