Stylish and Trail-Ready: 5 Outfit Ideas for a Hiking Date

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Heading into the great outdoors doesn’t mean you have to leave your fashion behind. We have ten chic and practical looks that are full of outdoorsy style.

Heading out for some fun and adventure? Welcome to the hiking date! Whether it’s a lowkey walk in a local or state park, or a few hours of romantic aerobics with breathtaking views as the reward, it’s essential to choose clothing that not only looks stylish but also provides comfort, functionality, and protection for your outdoor activity.

We tasked our outdoor-loving Editors to share some of their all-time favorite stylish and practical wardrobes for wearing on a hiking date:

Hike Fit #1: Easy Does It

Our first fit is perfect for an easy, open trail hike that’s less about elevation and more about conversation. Because the activity level will be moderate, a light-support athletic bra is fine for support. Adidas’ Purebare is a great choice. Over this we layer Topo Designs’ River Tank in a fun, abstract camo. Not only does this tank moisture-wick to keep you cool, it’s made with an anti-odor treatment and has an SPF of 30+. And who could say no to these cute cargo shorts from Paige? They have plenty of pockets, a nice, easy fit, and we’re loving the vintage green color. For shades, we pull in a great polarized pair from Blenders called Forest Flight (part of their Motion collection). Rugged frames, scratch-resistant lens and rubberized nose tips make sliding these on a no-brainer. Another nice thing about easy trails? You don’t need a hiking boot, though you’ll definitely want to wear a good walking shoe. On Cloud’s OC 5 Coast certainly falls under that category. And with this being a shorter hike, a small slingback backpack, like this one from Hydro Flask, is plenty big for carrying your water bottle (this 24 oz from Contigo works) and any snacks for along the way.

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Hike Fit #2: Baby, It’s Hot Outside

If your hike is happening when the temps are hot, you definitely want to dress appropriately. One big no-no for hiking while hot is wearing cotton. Why? Because it retains moisture. So all that sweat you’re pouring out is going to sit in that fabric, and that can make things feel pretty uncomfortable. Instead, you want to opt for technical fabrics designed for outdoor activities.

This light and colorful sports tank from Summersalt not only breathes beautifully, it comes with its own built-in sport bra (nice!). We paired it with another tech fabric choice – Alo Yoga’s Ivy League shorts, which are made of ultralight, quick drying material. And of course, the short, dolphin cut is so on trend right now. ASICS Fuji Lite 4 trail shoes are made for trail runners, so they’re grippy, but ventilated to keep your feet happy. Tifosi Optics’ awesomely sporty shield shades are also made to ventilate and keep your sunnies from fogging up. Having CamelBak’s waist pack is a great option for hands free hydration. Along with various pockets for snacks and essentials, it has a built in 1.5 liter water reservoir that you can sip as needed. Something you should definitely include in that pack is a cooling towel. If you’ve never used one, you simply soak it, wring it out, give it a solid snap and presto! you have a fast way of lowering your body temperature. This one we found at Target comes in a pack of four, so feel free to share with your hiking buddy. Finally, just for some fun, slide on Baublebar’s colorful jelly bracelet. It’s lightweight, waterproof and can be customized with your name.

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Hike Fit #3: Variable Temps = Multi-Tasking

Good things can come in small packages, and there are plenty of short hikes out there that can offer high reward for (mostly) minimal effort. Something that, say, starts through dense pines and ends in stunning, open vistas, or begins in open brush and ends with you nestled in old growth forest. In cases like these, you’re dealing with micro climates, and the best way to handle that is with materials that multi-task.

One of our hiking Editors favs for a variable hike are convertible pants. These stylish ones from Backcountry look like a cool pair of cargos (perfect for guarding against underbrush scrapes or rashes) but with just a quick zip they’re cute, sporty shorts. In a similar vein, Brooks’ convertible jacket will keep you covered until you’re ready to remove the sleeves and fold it into a lightweight vest. Underneath, Alo Yoga’s Real Bra Tank combines, you guessed it, a full support bra and seamless tank overlay that hits mid-stomach for the perfect crop top. For your feet, Palladium Boots’ Pampa Lite boot weighs in like a sneaker and Smartwool’s cushioned hiking sock will keep the spring in your step. Polarized shades are always a safe bet to keep your eyes clear and focused when moving between sun and shade. These sky blue with desert-hued stripes sunnies from Knockaround just emanate casual cool. Last but definitely not least, when you’re heading into brush or forest, don’t forget the bug spray! Pop this travel-sized spray pump from STEM in your bag and apply liberally (it’s Entomologist tested, made with botanicals and contains no dyes or fragrances).

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Hike Fit #4: Don’t Rain on My Fun

With summer comes summer rains, and if you’ve been checking your weather app and your hiking date looks a little damp, there’s no reason to cancel. A bit of preparation on your part will have you staying comfortable and stylish.

This fit starts with Smartwool’s Ultralight Hoodie Jacket, that’s heavy on the waterproof, but ultra lightweight in material. And when the sun comes out, it packs into the right hand pocket for easy storage. Underneath we add a tanklette (combination tank and bralette) from The North Face, that’s made from quick drying EcoActive fabric. To this we pair some quick-drying, moisture-wicking, fast-drying leggings from Smartwool. To help us keep our sure footing, we add the adidas TERREX Swift R3 hiking shoe, where the GORE-TEX membrane seals out wet conditions and the Continental™ Rubber outsole grips any surface, wet or dry. And because lighting in inclement weather is constantly changing, we grab a pair of Zenni Optical’s fresh and fab aviator transition lens sunglasses. Finally, for a little splash of color, Zoe Lev’s beaded turquoise necklace finishes this fit sweetly.

 

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Outdoor Fit #5: It Ends on the Beach

After a hot dusty hike, nothing beats a fun dip in the lake, ocean or waterfall. If this is your hiking date game plan (and this is one of our favorites too BTW) then it’s really important to choose your outfit, and your accessories, thoughtfully.

We start our fit with a pair of Backcountry’s river shorts. These 3.5″ inseam shorts are loose and comfortable for your hike, water friendly while you’re splashing around and super quick drying once you’re out. Up top, we pair a colorful collab sports bra from adidas and Farm RIO. It’s medium support and quick drying, so perfect for a dip. Next, check out these Techamphibian hiking/water shoes from Salomon. Perfect for keeping your feet stylishly protected on land and sea. Speaking of water, adding a pair of Blender’s Float2O Pro sunglasses is a smart idea. They are made to float for easy water retrieval. They’re also polarized, anti-salt coated, and have plenty of anti-slip grips to keep them on while hiking. Keeping your supplies together is the perfect job for Osprey Packs’ Daylite sling bag (made for day hiking) and in the event that you do have some wet items you want to keep separate, Thirsties wet/dry bags are about the size of a plastic gallon bag, but so much better for the environment. Lastly, Baublebar’s summer beaded necklace is a water-friendly way to add a big burst of color to bring the whole fit together.

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Outdoor Fits #1-5: Stashing Your Bag

Regardless of which outfit you decide, there are some universal items that should always be in your bag when you take a hike. Starting with that all-important sunscreen. You’ll want something that lasts a long time, sweat resistant and preferably water resistant as well. Neutrogena’s oil-free 70+ face sunscreen is a great choice, as is Bare Republic’s 100+ SPF adventure protection spray (it’s an ocean-friendly favorite with surfers). A moisturizing lip balm, like Burt’s Bees, is easy to pack and will keep those dry lips at bay. Something new that’s come on our radar is Brita’s stainless steel reusable water bottle. It comes with a built-in, replaceable water filter that really does its job taking the funky taste out of those random water stations. No matter how long the hike, it’s good to pack some quick energy, like a Kind bar. An easy-breathing, collapsible hat is also a necessary must, even if most of your hike is in the shade (a quick spray of bug spray on it before putting on will help keep those nasties away). Last, but not least, while injuries are never planned, it’s always good to have a mini first aid kit stashed in your pack. This one by Champion Sports has lots of items from band-aids to tweezers, all in a container the size of your phone’s power bank.

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