Have you ever gone hiking? I’m not what you would call an avid outdoorsman, but I do love a good adventure.
I also like to dress well, no matter what I’m doing. I have a feeling you do too.
Most people don’t even think about looking good when they’re gearing up for a hiking trip. And there’s nothing wrong with that.
When you’re deciding what to wear for your hiking trip, your priorities should be:
…in that order. When it comes to outdoor activities, you should never sacrifice safety or comfort for style. Function over form, always.
In fact, most experienced hikers or avid outdoorsmen probably wouldn’t even include style on their list of priorities.
On that note, I want to be upfront about my lack of expertise around hiking and outdoor activities:
To say I’m an amateur hiker is an understatement. I’ve only been hiking a handful of times. I don’t have a closet full of gear, and I don’t know much about equipment or hiking safety.
If you need info about that stuff, you’ll have to find it somewhere else. The goal of this post is to answer one question:
Can you be comfortable AND look good while hiking?
The answer is yes, but it takes a little effort, especially if you’re a shorter gent.
The problem is, most hiking apparel is long and baggy. For example, a men’s small shirt from REI – one of the most popular outdoor gear companies in the world – fits me like a two man tent.
Not only does this look ridiculous, but it’s not comfortable at all. A more relaxed fit might be comfortable for scrambling over rocks and climbing hills, but too much extra fabric becomes a liability and a source of discomfort.
I went on a week long hiking trip in Utah with a huge group of friends. We hiked everyday. Our trails included everything from steep, rocky ascents to narrow river walks. We dealt with daily temperature swings from 47 to 97 degrees Fahrenheit.
We also spent a night in Las Vegas and a few days in LA, so I needed some non-hiking outfits as well.
I like to pack as lightly as possible. Here’s what I brought:
- 3 pairs of quick dry boxer briefs
- 3 pairs of wool hiking socks
- 2 quick dry t-shirts
- 2 normal t-shirts (1 wool, 1 cotton)
- 1 short sleeve button up shirt
- 2 pairs of quick dry shorts
- 1 pair of chino shorts
- 1 pair of chino pants
- 1 pair of leather sandals
- 1 pair of
- 1 pair of hiking shoes
- 1 light jacket
- 2 pairs of sunglasses
- 1 hydration day pack
Let’s go into more detail about some of these items:
Quick Dry Boxer Briefs
For any type of physical activity like hiking, wearing cotton boxers is a bad idea. I recommend synthetic, quick dry boxer briefs for three reasons:
- They sit closer to your body (no bunching)
- They wick away moisture (like water or sweat)
- They can be washed in the sink and dry in 10 minutes
For this trip, I tried out two different brands – REI and ExOfficio. Both are comfortable and durable. REI underwear is slightly more affordable, but I found ExOfficio to be a little more comfortable.
If I could only wear one pair of underwear for the rest of my life, it would be the ExOfficio boxer briefs.
Quick Dry T-Shirts
When you’re hiking in hot weather, you want to stay cool and dry. Any fabric that absorbs and retains moisture, like cotton, is a bad idea.
Quick dry, moisture wicking fabrics are ideal. But just like with normal t-shirts, quick dry t-shirts are usually too big for men of modest height.
After a lot of hunting, I found a couple of tees that fit perfectly. My favorite is the Nike Youth Academy Training Top (XL). Made in boys’ sizes, the XL fits me well (not too long) and dries quickly.
These are also good options:
- Black Diamond Deployment Pocket Tee (XS) – Made from a wool/nylon blend, comes in handy during cool morning hikes.
- Brooks Infiniti T-Shirt (XS) – Made for running, fits like a glove, protects against the sun and keeps you dry.
Just don’t limit your search to clothes strictly made for hiking. In my experience, climbing, running and biking gear tend to fit much better.
Quick Dry Shorts
Every pair men’s hiking shorts I tried on was way too big. Too long, too wide, too everything.
Naturally, I decided to check out the women’s and young men’s departments. This worked out well, especially at REI. Here’s what I ended up with:
The Joshua Tree shorts were a bit longer but slimmer fit. The Venturi shorts were roomier through the leg but stopped right above the knee.
Both were comfortable for hot and sometimes wet summer hiking.
Just remember: when you can’t find anything that fits in the Men’s section, don’t be afraid (or too proud) to check the Women’s and Boys’ departments.
I brought one pair of pants for this whole trip. They might be my new favorite pair of pants. Slim fit, comfy and durable, I’m talking about the Aviator Chinos from Ministry of Supply.
Don’t be fooled by the name. These aren’t your standard cotton chinos. They’re made from this stretchy fabric that breathes, dries quick and moves with you.
But, unlike actual hiking pants, the Aviator Chinos are slim and tapered (similar to the Banana Republic Fulton), and they don’t have any obnoxious details.
I wore these pants throughout my trip – while partying in Vegas, hanging out in LA and watching the sun rise in Bryce Canyon.
They aren’t cheap, and they only come with 34″ inseams. But MoS will pay for you to get them hemmed (just send them your receipt).
These three pairs of shoes were all I needed for a casual summer adventure:
- Vans for J. Crew (grey canvas)
- Birkenstock Milano (these have the back strap)
- Merrell Hydro Hikers (hiking shoes that can get wet)
I actually found an old version of these Merrell hiking shoes at an outlet store. They didn’t have any men’s models in my size, so I went with the women’s version in size 9. Worked out perfectly.
Lots of footwear is unisex, so don’t hesitate to check the women’s section for something that fits your feet.
Also, you need good socks. I recommend REI quarter length wool hiking socks.
Sunglasses & Backpack
I love my Warby Parker Becketts, but these aren’t good for any sort of strenuous physical activity. They’re heavy and could easily fall off.
For running and hiking, I wear these sports sunglasses.
Note: As someone pointed out in the comments section below, you might want to wear a hat to protect your head and ears from the sun.
Just like other accessories, small bags and packs work best for shorter men. You should carry the smallest possible bag that fits your needs.
For this hiking trip, I needed to be able to carry two liters of water, my phone, sunscreen and some snacks.
Any small hydration pack will do, but I like this one.
You should never sacrifice safety or comfort to look good, but it is possible to hike in style. You just have to make sure your clothes fit.
This might require shopping in the women’s or boys’ departments, and that’s perfectly fine. If it fits, wear it!
Do you hike? What do you think about my outfits? Leave a comment!