Since this blog does not cater to lumberjacks and foremen or construction workers we will omit the work boots category and stick to the remaining three. Sorry guys, maybe you can do a Google search for "beard and boots, what works?".
Sporty boots can fall under the category of casual boots as well. Ergo, in an effort to maintain this blog rather short and not too long, we will condense them into one. Please, keep your Lugz Boots to yourselves. High School ended years ago, grown men should avoid these at all costs. They're too heavy, too thick, not subtle at all much like this bowtie:
Casual boots are great, let's focus on one of the most popular styles, Chukka boots. Not to be confused with the Jewish Holiday of Hanukkah, which given its 8 days of gift exchanges, I would not mind a new pair of nice boots 8 days in a row...
A great quality Chukka will run you a decent amount of money, as most good quality footwear will. Amsterdam Designer Mark McNairy carries beautifully done pairs of these. You can find very nice Chukkas here at Bonobos.com along with several other nice collections of sporty/casual boots to fulfill all your materialistic Winter needs. This blogger may be a bit biased because Bonobos does offer great customer service and I am very happy with my Chukkas:
A second recommendation would be Sebago boots or even Sperrys. The below Sebago Fairhaven Dark Brown boot is a gorgeous thing to wear and quite sporty for a casual night. Sperry also offers great pairs of Chukkas and regular boots. Make sure to visit both sites for your footwear needs.
Since Sporty and Casual have been tackled at once, let's now focus on dressy boots. Allen Edmonds (thanks to Dappered.com for the introduction) makes an out of this world pair of boots that go by the name of "Dalton". Such a powerful rubric could only be assigned to a pair of footwear worthy of its caliber. This comes in two colors, Walnut Burnished Calf and Dark Chocolate Calf:
For a cheaper alternative, one can go to Hugo Boss, Ralph Lauren and Zara. All three have outstanding pairs of boots that may not cause such a huge dent in your wallet. One particular pair that stood out in the options presented by Zara was their Dressy Ankle Boot. Reminiscent of a wehrmacht style marching boot, this gem looks good with both a casual or a more dressed up outfit.
Just make sure to bend your knees when using these while walking, lest you want to end up looking like these guys:
In closing, when wearing these boots with pants, feel free to tuck your pants into boots that are worthy of being shown. However, do not allow the pants to bunch up like a pile of toilet paper in the corner of a public bathroom stall, disgusting image right? Exactly the point. Keep them neat and orderly. Another option is to fold the pants up a bit to display more of the boots (my preferred style). This results in a cleaner look and it also displays enough of your footwear for those observant enough to compliment you on your amazing pair of boots. One thing to avoid would be folding Dress pants with boots, not a good look at all and if the pants are of good quality, chances are the folds will have a hard time staying in place. It's quite sloppy. Avoid it.
Good luck with your BOOTy calls for Winter. Au revoir.