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What to Wear on a Hiking Date – Beautiful!

What to Wear on a Hiking Date – Beautiful!

I’ve gone on quite a few hiking dates. They are really fun, except when you get to the age-old dreaded question of “what should I wear on my hiking date?”

I still remember while I was out on a trial and I came across a couple on their date. They just reeked off being newbies, and I just had to giggle.

The man wore hiking boots, which were probably brand new, and after a few miles, he really struggled to walk. He was also overdressed, and sweat was pouring off him.

The lady … She wore a tight mini skirt and tiny top in a bid to look sexy. Thank goodness she wore sneakers; otherwise, I’d have laughed out loud.

This isn’t to say you can’t and shouldn’t wear a skirt on a hiking date, but what is the best outfit?

What Should You Wear on a Hiking Date?

No one on a hiking date should ever look frumpy. Choose clothes that’s made of moisture absorbing or moisture wicking fabric (dates don’t want to see sweat stains) and appropriate for the difficulty level of the hike, the weather, and season. Guys can choose between hiking shorts or pants and a T-shirt or tank top, a jacket or sweater if it gets or is cold, and outdoor sandals, sneakers, or hiking boots. Ladies could choose between a hiking shirt, shorts, three-quarter or long pants, a tank top, T-shirt, or hiking shirt, a jacket, and outdoor sandals, sneakers, or hiking boots. A hiking date outfit doesn’t need to look too athletic; there are many cute, attractive, and fashionable options on the market these days to look your best.

How to Choose the Right Hiking Date Outfit

Choosing the right hiking outfit for a date isn’t simply about putting on clothes in which you look cute. Instead, there are two factors you should consider and then build your outfit around these:

The Trail and Difficulty Level

The terrain difficulty level is a big factor for what you should and shouldn’t wear on a hiking date. If it is an easy hike, whether you are a newbie or pro, then ladies can easily wear a hiking skirt.

If the hike is moderate to strenuous, then wear leggings or hiking pants. For guys, this is easy as they can simply put on shorts or opt for hiking shorts or pants.

Your shoes also play an important role. For easy terrain, where you are mostly walking on level ground or a slight up and downhill, wear outdoor sandals or walked-in sneakers or light hiking trainers.

If the terrain is rough and rocky, for example, then something that supports you more and keeps your feet safe like walked-in hiking boots would be better.

The Weather and Season

This is probably a “duh” section but I would like to emphasize how important it is to dress according to both the weather and the season.

For summer or warm weather, I usually dress coolly but also layer my clothes because I’m usually a little cold before the hike really starts. I also have a rain jacket in my backpack.

For mild winters, I dress similarly to how I do in summer, except for wearing long sleeve tops and long pants.

If the hiking date is taking place during winter and it’s snowy, then I layer with a hat, gloves, insulated hiking boots, thick, thermal socks, and thermal undies.

I ensure there are microspikes on my boots (I really don’t want to slip, whether it is a first date or the fifth!).

Layering also helps because the weather changes during the day and also depending on where I go hiking, so I can add clothes when it gets colder and windy, and take off when I feel too hot.

What to Wear on a Hiking Date

So taking into consideration the trail, weather, season, as well as never wearing not-worn in trailers, sneakers, or hiking boots, just what can you wear to look attractive?

The big no’s of hiking clothes are wearing jeans, 100% cotton, and anything that feels stuffy or restricts your movement. And if you are worried about sweating too much, check out these tips.

The yesses for hiking clothes on a date are:

…For Ladies

  • A hiking skirt that’s comfortable and allows you to climb and walk with ease.
  • Hiking pants – long, short, or three-quarters – that’s comfortable and lightweight.
  • Hiking leggings for hot weather; they are stretchy and comfortable and give you tummy control if you need it.
  • A hiking shirt, T-shirt, or tank top that’s designed for exercising (absorbing sweat) and fashionable.
  • A hiking jacket, sweater, or raincoat.
  • Shoes, so outdoor sandals for easy terrain or opt for worn-in sneakers or hiking boots.
  • Comfortable socks that’s made from polyester, nylon, or wool.

…For Men

  • Hiking shorts if the weather is hot (and if you have nice legs).
  • Long hiking pants for cooler weather or winter.
  • A hiking shirt, T-shirt, or tank top that’s moisture absorbing with minimal patterns and in a color that complements your skin tone.
  • A hiking jacket, sweater, or raincoat.
  • Shoes, so outdoor sandals for easy terrain or opt for worn-in sneakers or hiking boots.
  • Comfortable socks that’s made from polyester, nylon, or wool.

Frequently Asked Questions About What to Wear on a Hiking Date

What should a girl wear on a hiking date?

No matter what you wear on your hiking date, ensure you are comfortable. And being comfortable can be cute too. If it is warm, go for shorts or three-quarter leggings and a tank-top or cute exercise top. If it is cold, layer so you can take clothing items like a jacket off when you are warmed up. For example, you can wear a light jacket or sweater over a long-sleeve T-shirt.

Is going on a hike a good first date?

If you are not the outdoorsy type, then hiking might be a bit challenging, but this also depends on the terrain. Not all hikes are intense, and a date hike doesn’t need to cover back-breakingly difficult hiking terrain. In general, hikes make great first dates as first dates can be awkward and there’s plenty of visual prompts to be found in nature to help you make conversation. You can also find a nice spot to have a picnic at and just chat.

What do you talk about while hiking on a first date?

There are quite a number of ice breaker conversation activities and topics you could try out while hiking on a first date:

  • Where would you go?
  • Two truths and a lie
  • Favorite meal after a long, strenuous hike
  • Survival strategies during a zombie apocalypse
  • National parks
  • Memorable camping experiences
  • Would you rather – the hiking and backpacking edition


The Final Date

Hiking dates are awesome, whether you are the outdoorsy type or not.

Part of the fun is choosing a cute outfit that shows off your best attributes while being appropriate for the season, weather, and trail. Moreover, choose fabrics that don’t easily (or at all!) show any stains.

For ladies, I recommend wearing leggings, a tank-top, and worn-in hiking boots, and a jacket or cute sweater in your backpack. For the men, either go with shorts or long pants, a T, and also take a jacket in case.

Happy hiking!

About Me

Hi, this is Kent Walker. I am an outdoor enthusiast. I love fishing, hiking as well as kayaking. I write about my adventures in the wide open and what I learned about it.