I'm sure a ton of traditionalists will hate me for even proposing the option of shorts but I spend a lot of time in Texas and Madrid where I'm sure you already know, temperatures easily can be +40º if not hotter in the summer (plus I'm younger so perhaps I am entitled to a bit of slack). Nonetheless though, if I could wear chukkas with shorts it'd be fantastic because with mild winters an occasion could be found to wear them almost year-round. I have a pair of dress boots for colder times but I quite enjoy the styling of chukkas. They are pretty low cut which is the only reason I would ever consider wearing this "boot" with shorts.
I can't seem to make the call myself nor can I seem to find a lot of supporting evidence for my case via Google. Most pictures are some awful compilation of some awkward chukkas paired with those plagued cargo shorts. So, what would your opinions be on this subject? Is it acceptable or are chukkas more suited to be paired with the cuff of pants?¿ Inseam seems to always be an issue when pairing shoes with shorts so if anyone cares to know, most shorts I own have an 18cm inseam.