How to Wear Hiking Boots with Shorts?

Wearing hiking boots with shorts is one of the best ways to look cool, casual, stylish, and of course to stay cool on the trail during the summertime. Unless you are hiking in freezing temperatures, every guy will wear shorts at one point. Often I see people wearing shorts the wrong way and it just makes them look really bad. So I want to talk about the right way to wear shorts with a pair of hiking boots.

Shorts are inherently casual but that doesn’t mean they have to look sloppy or adolescent. Most guys aren’t wearing shorts correctly and that sucks because you know it makes them look bad and the whole point of clothing is to wear clothes that enhance your look, not clothes that detract from your look.

So these are a few things to consider when wearing shorts with hiking boots or vice versa.

Shave your Legs

Hormones work differently on each one’s body. So if your legs have less hair, you don’t need to shave your legs. In contrast, if your legs have more hair, trim them using a hair trimmer, scissors, or shave them completely if you don’t care about society.

Wear the right pair of Socks

Finding a good pair of socks for summer hikes can be challenging. Many outdoors experts think that wool (a natural fiber) socks can be beneficial especially when it is coming from merino sheep. Crew-length socks are generally worn when it comes to shorts. They also keep your boots from rubbing against your skin.

Know the Terrain

If you are planning to hike where you expect the trail to be mostly hard rocks, shorts may be perfectly fine. On the other hand, if you’re hiking in the bushes, you may consider switching to full-length pants or you can wear your crew socks with your shorts.

Length of your Shorts

Ideally, your shorts should be two inches above your kneecaps. I believe that your shorts should not go past your knees. They should stop right at the top of your kneecaps. It’s okay if you like shorts that are a little bit shorter or if you like mid to lower thigh, that’s perfectly fine. Personally, I don’t think any man looks good in shorts that go past his knees. Before you get your pitchfork out, remember this is just my opinion. If you like to wear long baggy cargo shorts, that is perfectly fine. But I have done a lot of research and I’ve thought a lot about this and I truly believe that men look better in shorts that are shorter and don’t go past their knees. They’re called shorts for a reason because they’re not capris.

Hiking shorts come in a lot of sizes and they are measured along the inseams like other pants. For example, 5, 7, 9 inches, etc. But for most folks, I think the sweet spot is between 7 and 9 inches. If you’re on the shorter side like me, a 7-inch short is going to look good. If you’re on the taller side or if you just have long legs, a 9-inch short is going to look good.

I would stay away from anything longer than 9 inches. If you are a shorter guy like very short or if you have very short legs or if you want to show a little more thigh, you can definitely go with like 5 or 6 inches.

Width of your Shorts

Besides length, you also have to pay attention to the width or the leg opening. The vast majority of guys that I see wearing shorts in the summertime are too wide, which creates a trapezoid shape. This is not a very flattering shape for a guy. It also makes your legs look really thin and wimpy. So the goal is instead to have a nice gentle taper from your waist down to your knees or from your hips down to your knees. It’s just like with pants. You don’t want them to be too skinny or tight but to kind of follow the shape of your legs.

Style and Details

Stick with solid colors or small-scale patterns. Solid colors are always a safe bet like khaki, tan brown, black, navy gray, olive, etc. These are all great colors for shorts. If you like patterns, floral prints, polka dots, or anything like that, that’s fine too. I recommend keeping them small like small dots or checks.

What Shoes to Wear with Shorts

Well, that depends on the trail you will be hiking on. Boots are generally rugged and provide protection against rocks, roots, and water. On the other hand, if you expect the trail to be easy, you may also consider lightweight shoes, trail runners, or even tennis shoes if you will be walking mostly on pavements.


Shorts are a great alternative to pants for hiking in summer. They keep you cool on the trail and offer much better breathability than full-length pants. Most hiking shoes and boots will go with shorts but you need to pick them carefully depending on the situation like weather conditions, terrain, and trail difficulty.