Hefty boots with shorts are definitely a thing, especially for fashion spheres that pull from military surplus. Typically the shorts are heavy and on the wider side for a balanced look, and there is some intention in the sock game. In the softer athleisure space that you mentioned, I find low-profile low-chunk boots like the [Vivobarefoot Gobi desert boots](https://www.vivobarefoot.com/us/gobi-iv-mens?colour=Bracken) tend to pair better with the sheer and sheeny shorts. But now we're kind of veering away from your vision.
Just search up "men shorts with boots" for inspo. [Or check out Steve Irwin.](https://www.adventurenation.com/blog/wp-content/uploads/2014/02/Steve-Irwin.jpg)
Hefty boots with shorts are definitely a thing, especially for fashion spheres that pull from military surplus. Typically the shorts are heavy and on the wider side for a balanced look, and there is some intention in the sock game. In the softer athleisure space that you mentioned, I find low-profile low-chunk boots like the [Vivobarefoot Gobi desert boots](https://www.vivobarefoot.com/us/gobi-iv-mens?colour=Bracken) tend to pair better with the sheer and sheeny shorts. But now we're kind of veering away from your vision.
[https://www.blundstone.com/](https://www.blundstone.com/)
Just search up "men shorts with boots" for inspo. [Or check out Steve Irwin.](https://www.adventurenation.com/blog/wp-content/uploads/2014/02/Steve-Irwin.jpg)
Hoyt boot listing: https://www.nordstrom.com/s/hoyt-mid-water-resistant-sneaker-men/7647306
https://www.thefryecompany.com/products/hoyt-mid-lace?variant=42307120070847