What should you wear on a hiking date, especially when it's the first time you're going to meet someone? Should you wear your regular ratty hiking clothes or spiff it up a little bit to make a good impression? Dressing up shows respect, and your date will notice you made an effort to impress them. Moreover, clean, well-fitting activewear or casual outdoorsy clothes show you’re prepared and thoughtful without being overly formal. You'll get style points for that. Whatever you choose, the key is to feel confident, comfortable, and put-together without sacrificing the practical gear you need for the trail.

How to Choose a Hike for a Date

On dating sites, everyone says they hike, but as you know, there are many different degrees of hiking prowess and experience. If you're thinking about suggesting a hike, gather some up-front information about your date's hiking experience before you suggest a route. If they're local and you're familiar with the trail system, ask them about their favorite hikes and when they last hiked, so you can gauge the distance and elevation gain they'd be comfortable with.

It's better to pick an easier hike with a great viewpoint so you can talk on the trail and get to know one another, rather than a more difficult hike where you're both huffing, puffing, and sweating uncontrollably. That won't be a good memory. Viewpoints are always a win, and if you can choose one they've never been to before, that's even better.

Here are some basic guidelines to help you spruce up a little:

Shirt: A moisture-wicking short-sleeve or long-sleeve shirt with a collar provides comfort for hiking and looks neat and intentional. Try: Outdoor Research Astroman Shirts, short-sleeve or long-sleeve. They're low-key but come in lots of different colors and patterns. They're also easy to wash, don't shrink in the dryer, provide some sun protection, and have snaps instead of buttons, so you never have to sew one back on.

Pants: Wear comfortable hiking pants or shorts in hot weather that suit trail conditions. On a first or second date, I'd avoid your Patagonia baggies and opt for something a bit less revealing. For shorts, I'd go with shorts with pockets, either cargo pockets or just side pockets. You have plenty of options. Tall, slimming pants are best if it's cool enough or if you want bug protection. For full-length pants, you can't go wrong with OR Ferrosi Pants or Rab Incline Light pants; both are sporty and have a subtle stretch that will show off your manly legs.

Hat: A clean, functional cap (avoid “crufty” or dirty hats) that protects you from the sun and looks good. A billed hat is better than a floppy wide-brimed hat, because you want your date to be able to see your face and profile. I'd recommend a hat with minimal branding or political beliefs emblazoned on the outside. If you have hair or aren't worried about sun protection, don't wear a hat.

Sunglasses: While sunglasses are a hiking essential, don't wear them or put them on intermittently during the hike. You want your date to see your eyes and feel your connection. Don't wear mirrored shades, period.

Shoes: Wear the closed shoes you normally wear for hiking. Just clean them off so they look used but not caked in mud.

Socks: Wear Darn Tough Socks. Your date will immediately know you're a classy guy.

Accessories: If a nose ring or ear stud is an essential part of your day-to-day getup, wear it. But avoid triggering a rejection by wearing too much male jewelry. Keep it simple and leave your heavy gold necklace or bear bells at home.

Layers: Bring a clean mid-layer you can give your date if they get chilled. Something warm and cozy, like a Squak Grid Fleece Hoodie or a Skygoat Pullover Zip Air 70, will go a long way toward making them feel comfortable and cared for. Don't forget to bring a rain layer for yourself and remind your date to bring one of their own, if the forecast calls for it.

Backpack: Bring a daypack that shows that you know what you're doing. In other words, don't bring your 65-liter Gregory Baltoro or a string backpack because you'll look like a geek. A 20-30L pack is ideal. Pack some snacks and extra water in case your date forgets theirs. Sun tan lotion, bug dope, a small first aid kit, and toilet paper may also be appreciated, and bring bear spray if it's recommended in the area you plan to hike in.

Smartphone:  Bring your phone so you can take a picture of the two of you together. Make sure your phone is in airplane mode because your date won't think kindly of you if you take a call during your date.

Happy Dating!

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