I find articles like these tricky. Every individual has their own sense of fashion, no matter how boring or creative which makes making bold claims about the best skirts (or anything else) for guys difficult to say the least.
That said, it’s still good to see advice out there, particularly for men who are just getting started on their beskirted journeys. There are so many different styles of skirts out there that it can be intimidating at first, so finding a good starting point is important.
The recommendations in this article look a bit too much like they just came off the runway for me, but others may find them inspiring.

THE BEST SKIRTS FOR GUYS
Skirts are for everyone, and here are 7 of the best skirts for men to wear in 2024.
https://www.ssense.com/en-us/editorial/market/best-skirts-for-men
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I found the best way to start was with a simple kilt. Sport kilt (a wrap kilt) is the easiest and more acceptable. Next try to match what you already wear. I found hiking skirts comfortable and don’t standout. Once you realize nobody cares or notice what you’re wearing then explore to styles you feel comfortable it.
That is a great way to start and is similar to how I started wearing skirts in public. Kilts are the perfect gateway drug so to speak since they are much more socially acceptable even if a little eccentric in some countries. It’s really just about learning to feel comfortable with wearing something that isn’t mainstream. Once you’ve done that, then the sky’s the limit!
“a bit too much”? Yeah, I’d say. Not one of these looks is real-world streetable, and I’d say never will be. Maybe in a few blocks in central London, UK – maybe. But daily wear: Nonsense.
Yeah, I agree with you there. Thinking about it now, I don’t know if such “advice” is more useful or harmful to men who are just beginning their journeys with wearing skirts. If they think they have to dress to extravagantly in order to wear a skirt as a man, then it might scare them away from it.
Because this post suggested the “styling skirts with Daniel Simmons” I watched that YouTube. They’re a bit annoying to watch but if you get to the meat of their YouTube, they mention something important.
If you didn’t grow up styling skirts, it’s such a new found reality it will take time to “get it right.” It will take experimentation to see what works for the male body wearing a skirt. Simply substituting a skirt for shorts doesn’t necessarily do it.
They made the point that they were adding a skirt to their already existing wardrobe and thought in the future they will be adding articles of clothing to their wards robe to go with the skirt in their wardrobe.
I thought that was pretty interesting.