I love me some leather boots, that is for sure. Am I an expert on them? No, not even close, I just know what I like and what looks good on me. The width of my feet are the standard 'D' size so I am able to fit in most Direct-to-Consumer brands. My feet are also are very shallow and creasing can become very noticeable on my boots. I have found that the cap toe style (as well as using shoe trees), compared to the plain toe boots help with that. Lastly, being in the Midwest means I should probably steer clear of 100% leather soles as the weather is unpredictable.
Below I listed what are the basics I look for in a boot for me. I have split them into two categories; "everyday wear boots" and "dress boots" as I have different criteria for each.
Everyday Wear, All Seasons Boots
From Left to Right: Natural Plaintoe Chomexcel Boots by John Doe Shoes, Arizona Adobe Rugged Captains by Thursday Boots, & PTC Collaboration Boot #2 by Santalum
Stylish, Fashion Boots
From Left to Right: The Troy Boots & The Rome Boots in Black by TAFT, Customized '48 Boots by Undandy, & the Dotter Boots by Velsaca
Top Left: Blake Stitched, Bottom Left: Blake Rapid Stitched, Top Right: Veldtschoen Welted, Bottom Right: Goodyear Welted
Left: Rubber/Leather Combination, Right: Studded Dainite Sole
If you are looking for great boot reviews and more about boots in general, I recommend the website Stridewise.