What to Wear on a Hiking Date: 16 Cute & Chic Outfit Ideas

Co-authored by Hannah Young and Aly Rusciano

Last Updated: October 9, 2022 References

The sound of rustling leaves, the sun on your cheeks, and your beautiful date beside you—is there anything better than a hiking date? You’ve been waiting for this day, and you couldn’t be more excited, but now you have to find something to wear. Before you hit the trails, take a look at these cute and practical clothing options for you to wear on your hiking date, no matter the weather. With this guide, you’ll be able to dress to impress even in the great outdoors.

Method 1

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Hiking Outfits for Warm Weather

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Stay cool and dry with a sweat-wicking tee. You’ll look sporty all while avoiding sweat stains! Pair this tee with your favorite leggings, jacket, and hat, and you’re sure to impress your date with your ability to think ahead.
- Sweat-wicking tees come in all shapes, sizes, and colors. Pick the style that works best for you and your body because, remember, your confidence will shine through.
- If you’re unsure what kind to go for, try a v-neck. These are super flattering on almost all body types.^{[1]
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- Stay clear of 100% cotton while hiking. This fabric isn’t sweat-resistant, so it’ll show off all the sweat stains, which is not ideal for your date.
2
Give your outfit a pop of color with bike shorts or a sports bra. Stylish and comfortable, these are great options for your date outfit. Not only will you be able to move freely during your hike, but you’ll also look great! Go for a matching bike short and sports bra set for a polished athletic look, or mix and match colors for a playful look.
- Make sure the material of your bike shorts and sports bra are moisture-wicking, meaning that they won’t pick up any other water besides your sweat.^{[2]
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- Try a pair of black bike shorts with a neon sports bra and gray muscle tee for a chill yet sporty look.
- Wear a matching animal print set and a neutral top to show that you’re put together and stylish.
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Wear hiking shorts for a cool, comfy vibe. Shorts are a great option for warmer months because they keep you from overheating. Less fabric gives your skin a chance to breathe and makes it easier for you to show off your hiking skills.^{[3]
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- Stay away from jean shorts when hiking as they can cause chaffing, and you don’t want to be uncomfortable while you’re trying to impress your date.^{[4]
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- Opt for athletic shorts that have a dry-fit material. This will help keep you cool and comfortable for the entire hike.
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Spice up your outfit with a cute tennis skirt. These skirts have shorts underneath, making them perfect for physical activity. You can move easily in them and look fabulous! Go for a bright color to stand out against the foliage, or try a neutral tone paired with an active tank top.
- Dry-fit and active material will be your best friend on your hike.
- Opt for a skirt with tight shorts underneath and a water-resistant material.
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Slip on moisture-wicking leggings for more coverage. Thin, easy-to-move-in material will be your best friend. You don’t want your clothing to hold you back, but you also want to impress your date. So, wear a pair of leggings that show off your curves and support you. Go for a matching set in a vibrant color to show off your playful side, or stick with classic black to pair with any top.^{[5]
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- Do the squat test before you leave the house. The last thing you want is for your date to find out your leggings are see-through! Stand with your back to a mirror, look over your shoulder, and then squat. If you can see your underwear, these aren’t the leggings for your hike.
- Pick a pair of leggings you know will stay up whether you walk, jog, hop, or skip.
- Try quarter or ankle-length leggings in the hotter months.
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Be prepared with a waterproof jacket. Layers will be your best friend on a hiking date. Even if the forecast doesn’t call for rain, it’s better to be safe than sorry! Start the hike wearing a lightweight jacket, and take it off if you get too hot during the hike. Not only is this practical, but it also gives a little reveal for your date.^{[6]
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- Tie the jacket around your waist for a trendy yet convenient look.
- Wear something extra cute or revealing under your jacket to give your date a show. Try a colorful sports bra or muscle tee that shows off your arms.
- No rain jacket, no problem! Lightweight flannels, hoodies, or athletic pullovers are great additions to your hiking wardrobe.
- It's always good to have a waterproof layer on when you're out hiking.^{[7]
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Protect yourself from bugs and underbrush with ankle-high shoes. No one likes getting bug bites or scratches from unsuspecting twigs and branches. Pairing your hiking sneakers with ankle-high socks not only gives you a retro look, but it also gives you peace of mind.^{[8]
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- Wool socks will help prevent blisters.
- Match your socks to your sneakers, so your date thinks you're one cool cat! For example, wear white socks with white sneakers.
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Add a hat for a cute outdoorsy look. Baseball caps, bucket hats, and visors will keep the sun away. Sunburn is the last thing you need on a hiking date. Hats are a great, effortless, and trendy way to keep your skin protected and ready for what’s to come after your date. Pick a hat that matches your outfit, and style your hair around it to look cute and ready for anything.^{[9]
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- You can always ditch the hat if you get too hot during the hike. Simply toss it in your backpack or loop it around your belt for later.
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Tie your hair up with a chic bandana. This is a super cute addition to your outfit in windy or hot weather. A bandana can keep your hair out of your face and help you wipe away any sweat. It’s practically the perfect hiking accessory! Tie it around your head like a headband, wear it on your neck, or twist it around your wrist.
- There are thousands of bandana patterns to choose from! Go for a classic look with gingham, or add some boho flair to your look with a floral design.
- Bandanas can also be a first aid tool if you or your date were to take a tumble on your hike. They work as makeshift bandages, rags, and even a tourniquet.

Method 2

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Hiking Outfits for Cold Weather

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Wear multiple layers for extra warmth on your hiking date. Fleece and tight-fitting undergarments are a must in winter. Hiking is all about layering in all types of weather, but especially in the colder months. It’s better to wear too much and take off a layer than to wear too little! Put an undershirt on under a sweater or hoodie, or opt for two pairs of leggings instead of one.^{[10]
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- Make sure your date layers up too! Text them before you meet up to make sure they’re warm and toasty before you hit the trails.
- You should have three layers for a winter hike: a base layer, a mid-layer, and a top layer.
- Start with a breathable base layer that provides some level of warmth and continue with an insulated down layer in the middle. Always have a waterproof layer with you at all times, too.^{[11]
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Get stylish with a cozy sweater. Merino wool will be your best buddy in the winter. The last thing you want is to be an uncontrollably sweaty mess for your date. Merino wool is breathable and moisture-wicking, making it ideal for cold hikes. Plus, there are hundreds of cute styles and colors of sweaters out there to choose from! Pick what makes you feel the most confident.^{[12]
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Throw on a hoodie for a classic, comfy look. Sometimes it’s just cold enough to feel a brisk chill. In this case, a simple hoodie is perfect for your date. Embrace the baggy look and rock a hoodie with your favorite artist on it, or tuck the front fabric up into the band of your sports bra or pants for more shape.
- Make sure to wear something underneath your hoodie—layering is key!
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Opt for fleece-lined leggings for extra warmth. You can stay cute, comfortable, and cozy on your winter hiking date without sacrificing warmth or mobility. Here are some things to look out for when buying fleece-lined leggings for your date:^{[13]
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- Make sure leggings are not 100% cotton.
- Pick leggings with few stitches to avoid bruises.
- Check that leggings are waterproof, especially if you’ll be in the snow.
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Stay comfortable with an insulated jacket. If you and your date are hiking through the snowy mountains, you may want to opt out of showing off those curves (for now anyway!). Function rules over fashion in this case, but that doesn’t mean you can’t look fabulous. Find a jacket that keeps you warm and makes those eyes pop.^{[14]
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- Puffer jackets, fleece jackets, and vests come in various colors, styles, and weights.
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Try insulated hiking boots to keep the cold out. Traditional hiking boots are typically ankle-high and have heavy treads for traction. These durable boots also have variations with fleece inside, which are a great option if you don’t like layering up your socks. Check out your local shoe store to see if they have any insulated hiking boots in your style.^{[15]
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- If you don’t want to buy new boots, no problem! You can layer up merino wool fabric socks to keep your toes toasty.
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Keep your hands warm with gloves. A pair of moisture-wicking and insulating gloves can help you stay toasty warm on your hiking date. Before you step on the trails, put on a pair of gloves and toss some hand warmers in your pockets. This will make sure your hands aren’t cracked when the trail’s over and you’re snuggled up with your date.
- Put on some lotion before sliding on your gloves to keep your hands happy and moisturized.
- Waterproof gloves are are perfect if you don’t want your hands getting wet if you fall in the snow.^{[16]
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- Gloves are an easy accessory to take on and off, and they weigh almost nothing in your backpack or pocket, making them a great addition to a frosty hiking date.
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Rock a beanie to stay toasty. Comfy and stylish, this is a great addition to your winter look. Opt for the classic pompom look, or go for a modern black beanie for a bit more edge. Use this winter hat as a way to express your style and show off a bit of your personality.
- Try a beanie with a fun character or animal on it to make your date chuckle.
- Pair your hat with a matching scarf and pair of gloves to make a bold fashion statement.