Help me settle something

Some wear khaki pants with black shoes, but I personally find the combination unattractive, and would, therefore, say that you are correct in your assertion that brown shoes are preferable with khaki. By cordovan shoes I assume that you aren't referring to shell cordovan leather, but to the dark burgundy color often associated with it; shell cordovan leather can be dyed many colors.  "Cordovan" colored shoes go pretty much with everything. Black shoes with navy are perfectly proper and are considered most formal, especially after 6 PM; this combination is certainly no faux pas; however, I personally prefer brown shoes with my navy suits, even after 6 PM, in all but the most formal situations. The balance of your list is consistent with what in my opinion is proper, but I would add browns to those shoes that can be attractively paired with white.

I have also seen brown and, more rarely, tan paired with gray and it has worked nicely, depending on the shade of gray.

He's definitely way off, and you are pretty much right. The only thing I'd modify on your list is the grey pants/brown shoes combo. This is (IMHO) one of the classiest combos out there. In fact, right now I am wearing a pair of brown perforated cap toe Alden balmorals with grey pants, a cream colored shirt, brown lizard belt, and a brown Loro Piana cashmere jacket with blue windowpanes. And yes, my socks match my pants--grey. Montecristo

I agree with most everything. I do think that navy pants with black shoes is acceptable, but I think the shoes would have to be very sleek to pull it off correctly. Shiny clunky oxfords makes me think of a USMC uniform... I completely agree about khaki w/ black shoes. I would never wear that combination... it looks really bad.

Khaki-coloured pants and black shoes are not the end of the world. It really depends on the shoes. More importantly, navy pants (or, certainly, a navy suit) and black shoes are standard in North America. Brown shoes with a navy suit, while acceptable in most circles, are far from conservative. Also: the closer the suit or pants to midnight blue rather than a true navy, the better off you are with black shoes.

brown shoes can work with grey and navy blue (i see this a lot in both london and milan) of course depending on the shade; black is a traditional pairing to grey and navy, especially in north america believe it or not, i've seen some very very high-end polished and very attractive deep brown-toned shoes that work extremely well with white pants, in addition to the traditional black in the reverse, black shoes can work with shades of brown pants as well, and can look rather fashion forward, as such, depending on the shade of brown (ie, biege and sands work well better than darker browns), don't immediately dismiss black shoes with brown pants

The only rule I follow are no brown shoes with black trousers (although I've heard of Italians breaking this rule to good effect.) I don't much like the khaki's/black shoes combo. My favorite combinations are dark tan or brown shoes with grey or blue, and black shoes with brown trousers. And with cream trousers, I always wear dark tan shoes.

I always go by the saying (which isn't really a 'saying,' I just made it up now) that: if you know The Rules* and respect them then you can break them if you want to--and I mean want, not out of some phony foppish rebelliousness. *I.e. what you can find in Esquire or any men's style book worth its salt.

This may belong in a different thread, but how do folks feel about the red green and purple shades of Shoes by Berluti? Every time I see them, the superlatives come to mind--stunning, breathtaking, masterpieces. Unfortunately, because I spend 5/7ths of my week in a business suit, I just can't see spending money on red shoes. For example, would these be suitable for navy or grey? http://www.berluti.co.jp/collection/espri/index.html In any situation other than Saturday and Sunday afternoons? I have several olive suits. Would shoes in the color of ankle boots on the bottom right page be suitable? http://www.berluti.co.jp/collection/index.html Bic

I hope no one mids that this comes a little late, but I wanted to add what I follow... If the khaki is light enough, I think it can look OK with black shoes. The more yellowish khakis look better with brown. And -- of course -- tan-colored khakis should be paired with brown shoes. I have no problems about wearing black shoes with navy pants. All of my grey pants are charcoal, so I wear them solely with black shoes. You listed white pants as going with white or black shoes, but I have some casual white pants that I wear with brown or black. The brown shoes I wear with them have a very orange tint to them -- and I found a belt that matches perfectly to the shoes -- so they might not be considered a true brown. The thing I will never do is wear brown with black.