Hiking Gear, Hiking Guides

What to Wear on a Hiking Date: Hiking Outfits for Every Season


The great outdoors has a way of connecting people, which makes hiking a great date idea. Hiking dates offer a unique opportunity to explore nature and your partner. Traversing beautiful trails while enjoying each other’s company is great, but deciding on a hiking outfit can be challenging.

You want to look stylish while being practical and comfortable outdoors. Keep reading to learn how to determine what to wear on a hiking date to maximize comfort, looks, and practicality.

what to wear on a hiking date

What to Consider About Hike Dates

Unfortunately, there isn’t a one-outfit-fits-all when it comes to hiking outfits. Instead, refer to circumstances and seasons to narrow down your outfit options. Consider the following factors when picking your outfit before a hiking date.

💘 Your relationship

The stage of your relationship might play a role in determining your hiking attire. That’s not to say that one relationship stage requires only one specific type of hiking style. Rather, you should assess your goals for the relationship and the date. What to wear on a first date hiking might differ from what to wear on a 100th date.

If you’re getting to know someone on a first or second date, you might choose to dress up a bit more to impress your partner while still being mindful of the hiking activity. On the other hand, if you’re in a long-term relationship, you may want to opt for a more casual and comfortable outfit to ensure ease and flexibility. Everyone is different, but your relationship comfort level and how you want to portray your partner will help you choose an outfit. 

🏔️ Type of hike and difficulty

Consider the type of hike you’ll embark on and its difficulty level. If it’s a leisurely walk on a well-maintained trail, you have more flexibility with your outfit. However, if you’re planning a more challenging hike with rough terrain or steep inclines, you must prioritize practicality and wear appropriate gear.

Use apps like All Trails to check out how tough or easy you can expect the hike to be. You can complete a short, mellow hike in running shoes and athleisure attire. A long and strenuous hike often requires hiking boots, more layers of clothing, and more gear like trekking poles and a backpack.

🌧️ Season

Possibly the most influential factor – and the one we will focus most on in this article – is the time of year. Depending on where you live, the season can significantly influence your choice of hiking outfits.

You’ll need to dress differently depending on the weather conditions and temperature. Hiking in the rain brings a whole host of new challenges when compared to a bright sunny day.

Let’s explore suitable hiking outfits for each season.

Summer Hiking Outfits For a Date: Experiment With Colors

☀️ Summer hikes often mean sunny and hot weather. To stay comfortable and protected, keep the following in mind:

  1. Choose lightweight and breathable clothing.
  2. Opt for moisture-wicking fabrics that help keep you fresh and dry.
  3. Wear comfortable and supportive hiking shoes or boots, along with moisture-wicking socks.

A fun pair of hiking socks can be a fun way to show your personality on a hiking date.

Remember to apply sunscreen, wear a wide-brimmed hat, and carry a lightweight backpack with essentials like water, snacks, and a map. No one wants to have to bail on a date due to a sunburn or dehydration.

A loose-fitting t-shirt or tank top paired with hiking shorts or breathable pants would be a great choice. Complete your outfit with a lightweight windbreaker or rain jacket in case of sudden weather changes. Hiking in the rain is no fun when you’re not prepared for it.

There are so many directions you could go with this style-wise. Summer hiking lends itself nicely to matching sets and playful colors. Ultimately, go with something that will protect you from the sun and make you feel most confident and comfortable.

  • ECCO Women’s Mx Low Tie Gore-tex Sneaker
    • GORE-TEX Technology
    • Breathable
    • 100% Waterproof
    • Multiple Color Options
  • Dibest Women’s Sports Tank Top
    • Stretchy & Comfortable
    • Embedded Support Bra
    • Elastic Under-Bust Strap
    • Soft & Skin Friendly
  • Willit Women’s Quick Drying Hiking Shorts
    • 100% Nylon
    • Moisture Wicking Fabirc
    • 5 Convenient Pockets
    • Zip Fly With Button Closure
  • Vansolinne Women’s Hiking Socks
    • Soft & Breathable
    • Pack of 4
    • Fun & Colorful Patterns
    • Durable Stiched Heal

Fall Hiking Outfits For a Date: Layer Your Look 

🍂 As the weather starts to cool down, dressing in layers becomes essential. Begin with a moisture-wicking base layer, such as a long-sleeved shirt or a lightweight sweater. Add a fleece or a soft-shell jacket for insulation. Opt for comfortable pants or leggings that allow ease of movement. Remember to bring a light rain jacket in case of unexpected showers.

As for footwear and accessories, choose sturdy hiking boots to navigate through the fallen leaves and uneven terrain. Consider wearing a beanie or a headband to keep your ears warm. Bring along gloves if the temperatures are colder.

It’s worth noting again that layers are your best friend for fall hiking dates. The good news is this allows you to style your hiking look in many ways throughout your activity.

  • Hibelle Women’s Full-Zip Fleece Lined Sports Hoodie
    • Lightweight & Stretchy
    • Quality Thermal Performance
    • Fleece Lined Material
    • 2 Hand Pockets & 1 Inside Pocket
  • Eddie Bauer Women’s Trail Tight Leggings
    • Multiple Color Options
    • High Rise
    • Moisture-Wicking Matierial
    • UPF Sun Protection
  • JMinger Women’s Lightweight Raincoat
    • Waterproof & Windproof
    • Drawstring Hood
    • Includes Carrying Pouch
    • Casual Loose Fit
    • Lightweight
    • Sweater Ankle Trim
    • Cushioned Insole
    • For Style & Adventure

Winter Hiking Outfits For a Date: Be Prepared, Bundle Up 

❄️ Get ready to bundle up for your winter hiking date. Winter hikes require extra preparation to stay warm and safe. Layering is critical to insulate your body, and you may want to add layers as you climb in elevation.

Start with a thermal or Merino wool base layer to wick away sweat. Add a mid-layer like a fleece or down jacket for insulation. Check the weather for signs of snow or rain.

Regardless, it’s a good idea to bring a waterproof outer layer just in case.

Wear waterproof and insulated pants to protect yourself from snow and wet conditions, and invest in quality waterproof hiking boots with good traction. Depending on how advanced your hike is, consider bringing crampons or traction devices for icy sections. Feel it out with your partner and do your research.

Don’t forget warm accessories like gloves, a hat, and a scarf. It’s also a good idea to carry hand warmers and extra layers in case of extreme cold. When it comes to winter hiking dates, it’s better to be over-prepared than under-prepared. If you’re comfortable, warm, and dry, you’ll have a better time on your date.

  • Merino Wool Base Layer For Women
    • Moisture Wicking
    • Adapts to Anyone’s Figure
    • Oder-Resistant
    • Ideal for Outdoor Activities
  • RAB Women’s Microlight Alpine Down Jacket for Hiking
    • Packable Protection for Mountain Pursuits
    • Eco-Friendly Materials
    • Water & Wind Resistant
    • Increases Warmth Where It Matters
  • UGG Women’s Adirondack Boot
    • 100% Leather
    • -32 Degree Weather Rating
    • Stays Flexible in Freezing
    • Extra Warming Insulation
  • Winter Beanie Hat Scarf Gloves Set for Women
    • Superior Fleece Lining
    • Touchscreen Fingers
    • Fluffy Faux Fur Pom Pom
    • Soft to Touch

Spring Hiking Outfits For a Date: Think Flexible

🌤️ Once again, layers are the name of the game with spring hikes. Spring brings fluctuating weather conditions, so dressing in layers is crucial. Begin with a moisture-wicking base layer, which you may want to be short-sleeved in case it warms up.

Next, choose a lightweight and breathable mid-layer. Wear pants or shorts that allow flexibility and movement. Convertible pants are convenient for spring hiking. Either you think they look super dorky or super cool. Decide for yourself and choose your date outfit accordingly.

Carry a lightweight rain jacket in case of showers. Spring can bring mud and flooding. As such, go for waterproof trail shoes or hiking boots with good traction. A good hat will protect you from the elements, whether sun or rain. 

On a hiking date in the spring, you can bring your outfit to life with a great hat. It’s also a good idea to bring a lightweight, packable puffer jacket that you can easily carry in case of sudden temperature drops.

  • BALEAF Women’s Quick Dry Long Sleeve Shirt
    • Lightweight & Quick Drying
    • Soft & Stretch Fabric
    • Hidden Watch Window
    • Curved Hem
  • Women’s Softshell Jacket, Fleece Lined
    • Wind & Water Proof
    • Stain Repellent
    • Durable
    • Fleece Lined
  • Cycorld Women’s-Hiking-Pants-Convertible
    • Moisture Wicking
    • 5 Pockets for Storage
    • Elastic Waist
    • Drawstring Hem
  • ANJOUFEMME Hiking Boots for Women
    • Ideal for a Casual Hike
    • Powerful Protection
    • Strong Traction
    • Soft Cotton Plaid

Year-round Gear For Hiking Dates

Hiking can come with more accessories than your average date. Apart from clothing, there are a few essential gear items you should consider bringing on a hiking date. Use the following as a gear checklist for your hike date. Short hikes might not require a complete set of gear. However, it’s better to be safe than sorry on a date.

●     Hiking backpack to carry water, snacks, and other essentials

●     First aid kit

●     Trekking poles

●     Compass or GPS device

●     Trail map

●     Hiking headlamp or flashlight

●     Multitool

●     Fully charged mobile phone

🚨 Safety tip! Before embarking on your hike, it’s a good idea to inform a friend or family member of your plans

What’s The Best Outfit to Wear When Hiking On a Date?

The best outfit for a hiking date strikes a balance between style and practicality. With your relationship, the hike difficulty, and the weather in mind, follow these general tips to choose the best outfit for you.

  1. Comfort is key.
  2. Dress for the occasion.
  3. Layer up.
  4. Remember protection from the sun and rain.
  5. Be mindful of style.

What works for guys on a hike isn’t the same as what works for gals. Let’s explore what types of hiking attire can help men and women feel like their best selves on a date. 

Best Hiking Clothes For Women to Wear On a Date

Ladies, you can slay the hiking date with comfort and style. The best thing you can wear in any season is breathable clothing that makes you feel confident. 

Brands like Patagonia, Columbia, or Prana sell a variety of cute and practical hiking attire. Rock fashionable hiking boots from Merrell or Salomon, and stay prepared with a trendy jacket from The North Face or Outdoor Research.

Best Hiking Clothes For Men to Wear On a Date

Gentlemen, gear up for an epic hiking date where you can look good while showing your athletic side. Functional hiking clothes with neutral colors are the best go-to for a date. 

Wear practical and fashionable hiking outfits with moisture-wicking tops and bottoms from trusted brands like Arc’teryx, The North Face, or REI

Step into adventure with sturdy hiking boots from Salomon or Timberland, and keep covered with a versatile jacket from Patagonia, Columbia, or Black Diamond.

The Bottom Line

Choosing what to wear on a first date hiking involves finding the right balance between practicality, comfort, and style. Consider your relationship, the type of hike, and the season when selecting your attire. 

Remember to prioritize comfort and choose clothing that allows freedom of movement. With the right outfit and essential gear, you’ll be ready to enjoy a memorable hiking date in any season.

Mitch Taylor
With over 20 years experience with camping and hiking, I've taken it upon myself to share my insights. From common camping and hiking questions to gear recommendations, your adventure starts here.

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