As a photographer who documents adventurous engagement sessions and elopements on hiking trails, I regularly help my couples navigate the process of choosing which outfits to wear and bring along with them, and much of the same advice applies to hiking dates. Believe it or not, choosing what to wear on a hiking date doesn’t have to be complicated. Yes, your hiking date outfit might get a bit more complex the longer and more strenuous your hike is, but for the sake of this article, let’s assume you’re looking at a day hike and not a multi-day backpacking adventure.
Not all trails are created equal, and what you wear will ultimately depend on the trail difficulty, length, and the weather on the day of your hike. The longer and harder the hike, the more complex your hiking date outfit is going to be. I’ll discuss a few different scenarios in this article, but when in doubt, it’s better to be over-prepared than under-prepared for your date.
I’ll start with discussing what to wear for warmer weather hiking dates and then I’ll talk about cooler conditions. From there, I’ll address the outfit flexibility that comes with shorter, easier hikes.
One thing to note: there’s a lot of hiking gear out there, but I don’t want you to ever feel the pressure to have to own everything. The tips and links I’ve included in this article are here to help you and ensure you’re entering the wilderness prepared. We all start somewhere, though. Whether you have lots of hiking gear or none at all, remember there’s a lot you can do with what you already own.
Disclosure: With some links in this article, I may earn a commission if you purchase, at no additional cost to you. There’s nothing I hate more than companies that recommend products they don’t actually love. These links are all from stores that I recommend to my clients and shop at myself. The links help support small businesses like mine and allow me to keep creating this free content for you.
For hiking dates on warmer days, what you’re looking for is lightweight material that will wick sweat easily. Another thing to keep in mind is that darker colors absorb more heat, so opt for lighter color clothing to reflect some of that heat and cool you off on your date.
In many mountainous regions, warmer months are also a bit sunnier, so having a baseball cap to shield your face from excessive sun exposure is a good idea. A ponytail can look super cute with one of these caps and will help keep the hair out of your face during the date.
Bandanas are also a cute option to keep your neck from getting burned, and they can add a little extra personality to your look. If your hiking date is on an overcast day, roll your bandana up and use it to tie back your hair, braid it into your hair, or roll it up into a thin strip to use as a headband to pull the hair back and out of your face.
Sweat wicking pants are a must-have for a hiking date outfit in the warmer months. For a more form-fitting look, I love these 7/8 length sweat wicking leggings (I’m on the shorter side, which makes 7/8 length leggings my personal fav!). I recommend getting them in the sage gray shade, since that’ll help keep you cooler than a traditional black legging. Same with this pair that has pockets!
Shorts are also a solid option during this season, but you’ll want to make sure you’re not on a trail that will involve brushing up against poisonous plants when choosing to go with shorts. For men, these shorts are moisture wicking and offer UV protection. Same with these water repellant shorts. For ladies, these breathable, sweat wicking, UV protected shorts are a good option. I personally think these comfy sweat-wicking gray shorts are also really cute.
For shirts, I like the look of this option for ladies and this option for guys. Both come in light colors, which’ll help reflect some of the warmth when you’re needing a hiking date outfit that doesn’t absorb that summer heat. They also are both moisture wicking and offer sun protection.
Also, if you’re trekking out to a hot spring or swim-friendly alpine lake during your hiking date, don’t forget to bring a swimsuit as a part of your hiking date outfit!
Layers are crucial for winter hiking dates. When crafting your hiking date outfit in the winter months, you’ll want to wear a base layer to seal in the heat, have water-wicking pants to avoid your pants from getting soaked when trekking through melting snow, and have various other layers that allow you to make the proper adjustments to your hiking date outfit without overheating.
Another commonly overlooked element in your winter hiking date outfit is gloves. Please please please do not forget this part, especially if you’re hiking in the snow. A thin pair of mittens also won’t really do the trick in chilly mountain weather. Get yourself a glove liner (my husband and I both own these touch-screen compatible ones), an insulated glove, and if you need the extra heat, slide in some hand warmers.
Having a beanie to wear during winter hikes is also really important. The last thing you want is insanely red and painful ears on your hiking date. A merino wool beanie like this one is a great option.
When my husband and I go on hiking dates, we both make sure to wear our base layer underneath. For guys, you’ll want a base layer top and bottom. For ladies, you’ll need the same: you can find a base layer top here and a bottom here. You’ll then put on the pants you plan to hike in.
For tops, we both swear by all things Patagonia. I have two different Patagonia fleeces that I switch between: the Better Sweater and the Retro Pile Marsupial Fleece. These both lock in that extra warmth I need on chilly winter hikes. Ed also wears the Better Sweater.
On top of everything, you may also need to add another jacket, like a puff. Some great options are the Norseland insulated parka for ladies and the Magma 850 down hoodie for men. When looking at jackets, always make sure their insulation levels match your needs and check to see whether the jacket runs small or large. That’ll ensure you’re able to properly layer your hiking date oufit.
If you’re hiking on packed down snow during your date, having MICROspikes will also be important.
I work with couples who literally hike in their wedding attire, so I’m a believer that not every hike requires super intense hiking outfits. For short hikes in good weather on calm terrain with minimal elevation gain, you can certainly wear a cuter hiking date outfit. I’d just make sure that your hiking date outfit is something you can easily move around in, and that you’re wearing proper footwear. If you ask me, good footwear is half the battle, so I have a section dedicated solely to hiking boots and socks after this section.
But what if you want to look cute and the hike you’re going on is a little longer? What do you wear then? When I photograph engagement sessions this happens a lot! Let’s say you want to enjoy a picnic at the top of the mountain and you and your partner don’t want to have your sweaty hiking clothes on while you eat.
You can hike up in something more comfortable and fitting for the type of hike you’re doing, and pack your cuter hiking date outfit in your backpack. You can easily switch outfits at your destination.
Hey, sometimes you just want to enjoy wearing that epic, flowy dress in the mountains. And I believe you should totally be able to do that. So hike up in something different and change at the top instead. Easy peasy.
I just want to reiterate that the hiking date outfit ideas listed in this section are solely for very easy hikes with minimal to no obstacles (and in good weather conditions!). When in doubt, please wear formal hiking attire, pack your cute outfit with you and change at the top. Safety on a hike is the most important thing, and if you feel like you can’t do it in a more casual everyday date outfit, please don’t.
When I work with my couples for their adventure engagement sessions, one of my favorite places to recommend for flowy, easy to move in dresses is LuLu’s. A few of my favorites from them are this cream color maxi dress and this black open-back maxi.
For guys, flannel shirts are not only a great looking option, but they’re also a nice and warm choice too. Super practical for a hiking date outfit. I also really love the inclusion of a beanie to keep your head and ears warm on hikes at higher elevation in windy areas.
One thing to note when putting together your hiking date outfit: it’s generally not advised that you hike in jeans or cotton pants because they take a long time to dry and hold a lot of weight when wet, which is not what you want when hiking. The only time I ever wear cotton leggings or jeans when hiking is when I know the weather will be sunny and I’m sure I won’t be running into water crossings.
Good shoes are essential for your hiking date outfit. Specifically, you’ll want to look for boots that have good traction to handle hiking over non-paved surfaces like slick rocks and muddy terrain. While comfortable clothes are certainly an important aspect of your hiking date outfit, the wrong shoes can make or break the experience.
This doesn’t mean that you have to wear a traditional hiking boot on your hiking date, though. My favorite brand of boots that I think look super cute are Kodiak. They’re a Canadian company, so they know how to build boots that are durable for the colder seasons, too. I highly recommend looking into their waterproof, insulated boots, particularly if your hiking date takes place at a higher elevation, where your toes will get a bit chilly. I personally own these Kodiak boots and adore them.
Kodiak boots are a great option if your hiking date is going to be under 4 miles round trip. For anything longer or more strenuous, a traditional hiking boot is going to be the best option. Danner boots are great for this. For an insulated, waterproof Danner boot, there’s the weatherized Mountain 600 for women and the insulated Mountain 600 for men.
If you’re doing a shorter, non-technical hike that involves wading through creeks, or if you’re just having a lakeside date with a casual hike, wearing Teva sandals is also a good choice. I love hiking in my Tevas for short hikes, or any hikes that involve sand (like sand dune hikes or beach hikes). Wear these sparingly on more mountainous trails, though, as close-toed boots are going to be safer for those types of hikes.
Pro Tip: Always make sure you give yourself time to break in your boots before wearing them on your hiking date. Some boots don’t require this, but many do, and the last thing you want is to be dealing with blisters on your date.
Believe it or not, good socks can truly change your hiking experience (and add a colorful touch to your hiking date outfit). Take it from a girl who used to wear her standard ankle-length socks with her boots and deeply regrets that she ever did that. I’m not going to lie to you and tell you that good socks are cheap. A nice pair of socks that’s suited for hiking, durable, and feels comfortable can sometimes cost $20 or $30. But trust me when I say they’re worth every penny. Cheap socks can easily lead to blisters and discomfort on your hike.
Plus, a cute pair of socks can definitely add some personality to your hiking date outfit. My favorite brand of hiking socks is Darn Tough. I literally have a pair that works for every season, and for good reason: they are incredible. If you’re looking for a warmer sock to pair with a winter hiking date outfit, the mountaineering over-the-calf pair is amazing. I wear mine with my snow boots and they’re awesome. You can find the women’s pair here and the men’s pair here. If you’re looking for a lightweight sock that can be worn during warmer seasons, this women’s sock is a good option. For guys, this pair is also an awesome choice.
Yes, your hiking date outfit is important, but so are the additional accessories that’ll keep you comfortable and safe on your date. For starters, I always recommend bringing headlamps (these are the ones I use, and they provide so much light), especially if you plan on enjoying the sunrise or sunset together. These will allow you to hike in the dark.
Packing bug spray (I use this DEET-free version and it’s great) and sunscreen are also crucial. Lakes and rivers are notorious mosquito magnets, even at higher elevations. And high elevation hikes above the tree line are the easiest places to get sunburn (even for those, like myself, who don’t normally burn).
Snacks and water are also essential for your hiking date, but the amount will vary based on the hike length. Hiking packs will typically have a compartment where you can slide in a hydration bladder for longer hikes. For a shorter hike, bringing along a reusable bottle is a great choice.
While not so glamorous, having a compact first aid kit is also essential for a hiking date. Even if the trail you’re having your date on might not be strenuous, cuts and scrapes can still happen, and it’s nice to have a band-aid or some ointment on hand.
For longer hikes, a day pack is definitely worth investing in. They help take the weight off your shoulders and place it on your waist, which makes longer hiking dates way more comfortable. If you’re planning on bringing along food and drinks for your hiking date, a pack will certainly help. I personally use the Osprey Kyte 36 pack and love it. It fits everything I need for day hikes, including food, water, and extra layers!
Another thing I highly recommend bringing along for your hiking date if you’re wandering deeper into the wilderness or doing a longer trek is some sort of satellite communication device, like the Garmin inReach. I bring mine on all of the adventure elopements and engagement sessions I photograph, when they take place in an area where there’s no cell service.
And one last tip before you take off on your date! Please make sure to download offline maps (you can do this through Google Maps) to ensure you get to your trailhead without needing data. Also, the app AllTrails has a pro version where you can download an offline map of the trail you’re hiking and see where exactly you are. Not all hikes are straightforward, and this app has helped me avoid getting lost on multiple occasions (plus, it’s nice to see your progress on the trail, too!).
Now that you’ve figured out what to wear on a hiking date, you can hit the trails on focus on the adventure you two get to go on together. Because let’s be honest, nothing quite beats the great outdoors.
P.S. As an adventure elopement photographer based in Colorado, I specialize in documenting adventures in the mountains, whether in a national park or your favorite hiking trail. I pride myself on not just documenting your elopement or hiking adventure session, but also helping you navigate the details as well — like sorting out the perfect hiking date outfit ideas for your adventure session. If you’re looking to have your hiking date documented as the epic adventure it is, I’d love to chat.
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