To differentiate the rustic work boots such as the waterproof military boots from the more aligned and social boots, you have to be aware of the level of formality, and for that, we always hit some keys around here when I talk about shoes. Are they:
The more texture the leather in the upper, the more casual
Suede is more casual than smooth leather, which is more formal than textured leather.
The lacing the shoelaces
Laceless boots tend to be more casual. Among the lace-up boots, closed-laced boots are more elegant than open-laced boots. As with shoes, oxford boots (left) are more formal than derby boots (right). You can better understand this difference between oxford and derby.
The thicker the sole, the more casual the boot is.
Rubber soles or double leather soles are more rustic and, therefore, more casual.
The lighter the leather, the less formal the boot tends to be.
As a rule, a black boot is more elegant than a light brown one. Of course, you have to pay attention to other features, but all things being equal, the dark color is almost always chicer.
The more rounded, or higher, the toe of the boot, the more informal
Social boots usually have a low toe. Work boots have sturdier toes. Extreme boots are exceptions (something too pointy or too square). They are exceptions because styles that are very off the curve go in and out of fashion.
Wider boots, with more robust shapes, are more casual
The “timeline” above shows how the shape impacts the boot’s elegance
Double, triple, or quadruple seams are signs of a boot to kick can and work. They are, therefore, more casual.
All these observation points interact to form a more or less casual boot. All of the various styles of men’s boots, without exception, have these different levels of formality. Over time, your eyes begin to notice these things, and you can incorporate any boot style into your day-to-day by regulating this level with the clothes you wear.
Let’s say you like lace-up boots but always wear suits? You can look for a darker, more elongated boot with smooth leather. Or that you like Chelsea boots but only wear baggy workwear pants? You can opt for a boot with rustic leather, rubber sole, and rounded shape.
That way, you choose the style and buy something that you will wear as often as possible. No more buying something and realizing it doesn’t match anything you have—waste of money and raw material.