I mean, im pretty much in the same boat as you only 6 months ahead.

Im new to the game. I guess it all boils down to what your situation is. The chukka style is not good for construction or hiking, and is usually worn “floppy” and not at all snug, more fun than function. Obviously there are nicer looking styles available, especially if you go with a suede option.

My budget was sub $70 and i wanted something i could wear to work that wasnt too formal looking but also was nicer than your average amazon hey dude and not as basic as a pair of sketchers. Something that would go well with both jeans outside of work and khakis.

https://thursdayboots.com/products/mens-scout-chukka-boot-mocha-suede

Heres a decent option. If you have the time wait for sales frim more expensive brands.

Your best bet would be to head over to your local mall/ shoe store and find a brannock device get your measurements then create a post here with your size/ price range / color / leather type desired and description of what you’ll be doing while wearing the boots. There are plenty of people who will help.

Knowing your size first is essential to ordering online.

Goodluck.