If you think about it, they probably go well together. Flapper dress is often quite revealing, and the shoes are intended for flapper, not work-boot. And while some men may wear a pair of loafers to work as a “casual Friday” pair, if you’re going with a flapper dress you might want to avoid the sneakers. Not only are they too flirty to be worn without a dress, but they create a bit awkwardness in situations like an office party where people might not realize that you’re wearing sandals under your work boots.
Now that we’ve got that out of the way, what shoes go well with a work boot? Many men have worn sandals underneath their work boots on the job for many years, but I’m not going to suggest that you go completely overboard and start wearing sandals all over your work boots. Instead what I want to focus on is shoes and boots together. The combination of sandal design and a work boot makes for a wonderful mix, and it is one that I have found to be quite comfortable.
When you look at all the sandals out there you quickly realize that not all of them are created equally. The type that work well with a work boot can often look a bit more polished and even a bit more “articulated.” The type that feel more formal will often make a little more of a mess than others. And the type that have some sort of unique and original feature (something I’m going to call “something else” for the rest of the article) almost always work best with a work boot. I use to joke about a guy telling me that whenever he sees a pair of sandals at Macy’s he thinks about how they work really well together with a work boot. And while I don’t have any real solid evidence as to who said it, it’s true.
What I’ve found most desirable are work boots that have an “outsole”; meaning that if you place your shoe in the outsole, the work boot doesn’t have to go through a complicated fit. These types of work boots will have a leather lining, or it could be a rubber lining, and it will be quite comfortable. But more importantly, a work boot has two or three pieces that are designed for working together, and they all have to be kept out of the way. There are really no other benefits and no downside to wearing a pair of sandals inside of your boots. You just end up having the feeling
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