Dear 100 Hour Board,
I have a pair of Dr. Martens Vernons. They are quite possibly the most comfortable pair of shoes I have ever owned. I usually wear them to work with jeans. I'm taking a new job that won't allow me to wear jeans in the office. I am hopeless when it comes to matching. I know "normal" khakis (you know, the light brown Dockers type pants) match. Can you please give me some ideas of what colors/styles of pants/slacks would match these shoes beyond the typical khakis? For example, would gray or navy slacks work? Any pointers you can give would be greatly appreciated.
Did I just hear a call for arbitrary fashion advice from people with a publicly unknown sense of fashion? Because I will happily oblige!
You are definitely right that light khakis would go well with the dark brown of the shoes. Just make sure to stay away from dark brown khaki/any color closely resembling the shade of the shoes. Excluding black, I generally like to wear articles of clothing that contrast with one another when the two articles will be adjacent when worn.
Really, the not-same-color stipulation is my only restriction to offer. The nice thing about dark brown shoes is that they go with just about everything. Perhaps if you wish to be super fashion conscious also avoid wearing the shoes with black/really dark gray pants. Personally, I especially wouldn't wear ever them with suits either (in the hypothetical situation where I wore men's fashion at all). So, for any dressy-casual outfit, I think those shoes are golden.