I did a list of recommended boots but here I enumerated pairs that are below $100. Yes, surprisingly there good affordable options for him (or you).
Eastland Men's Daily Double Chelsea Boot, Dark Brown described as flexible, slip resistant, insulating and durable.
Mens Black Leather Brogue Oxford Ankle Boots
A good partner as you navigate your life's journey. This pair, as time passes, changes to accommodate your feet. The leather is both strong and durable. #madetolastalongtime
Arkbird Mens Chelsea Leather Dress Boots
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Premium, comfortable, breathable - that's Arkbird's description of this wonderful pair.
Arkbird Mens Suede Leather Chukka Boots
Versatile and comfortable. This amazingly priced pair is available in different colors and sizes. You can level up your style (or his style) without breaking the bank!
Bruno Marc Men's Suede Leather Chelsea Ankle Boots
Service boots which serve your fashion style well. This pair is very versatile, use it for business or casual outfits.
SUREWAY Men's 6" Leather Ankle Lace-up
A unique and affordable style from ARKBird. Also versatile and comfortable. This pair has a simple accent which makes it unique and makes it more handsome. #itsthering
Arkbird Chelsea Ankle Boots Men Leather Oxford
You can be sure the quality is excellent because this pair comes from a family-run company with a reputation for making foot wear for generations!