2015 Update: Check out our latest thoughts about how to wear black and navy together. 

Reader T writes in with this request…

Could we please have a discussion about wearing blue/ navy with black? Today I’m wearing a navy sheath dress with grayish/black tights, black shoes, black belt and a gray cardigan.  I feel like I’m getting some weird looks. I feel comfortable in this outfit; it’s not boring and I’m sick of wearing this dress with flesh colored pantyhose and navy shoes.  I thought that this would be interesting! I just feel like people are “getting” this combo. What are your thoughts?

Pictured above:  Jessica Schroeder from What I Wore, wearing black and navy together.

To us, this sounds like a great outfit, with one important caveat:  that it doesn’t look like you got dressed in the dark.

For starters:  From everything we’ve read, yes, it is entirely appropriate to wear black shoes with navy. We can’t remember which fashion book we got this from (InStyle?  Elsa Klensch?  Debrett’s?) but the rule we’ve always read is that “black dresses navy up, while brown dresses navy down.”  Think about men and their suits — the navy blue power suit is almost always worn with black shoes.  (Or, occasionally, a dark red cordovan shoe.)  More specifically, think of naval and marine officers’ dress uniforms.  (Oooh, or there’s a great Audrey Hepburn movie called “How To Steal A Million” where we think she wears a navy Givenchy suit with black patent leather bag and shoes also, but we can’t find a screenshot of her in the outfit.)  It’s an interesting question whether, when wearing a navy skirt suit with tights and black shoes, whether one should wear navy tights (to elongate the skirt) or black tights (to match the shoes) — to be honest, we usually punt and wear sheer pantyhose in that circumstance.

In terms of wearing black and navy clothing together:  Again, we’ve heard from a number of fashion “authorities” that you can wear them together, and we’ve seen it in runway pictures, but … well, it’s hard to pair them together when you grew up hearing “don’t wear black with navy” over and over again.  So here’s the rule of thumb we’ve come up with:  if the navy is very close to a black — so close that in a low light it actually looks black — then you probably shouldn’t wear it with black, because people will think you got dressed in the dark and didn’t realize that it was navy. If, however, the navy is more on the blue/purple side — or some of them even have a good amount of gray mixed in — then wear it without fear.  If possible, accessorize to accent the fact that you know you’re wearing black with navy, and in fact have done so by choice — such as by pairing it with gray, or putting a black belt directly over a navy sheath dress, or… well, exactly what it sounds like you’ve done.

Now, on to the “weird looks” — our opinion has always been that as long as you’re not violating an “office”-y dress code (are your toes, breasts, and underarms covered?), pushing a societal button (do you look like a dominatrix or a ’50s housewife?), or otherwise looking like you’re in costume (Annie Hall? clown?  Joan from Mad Men?) then your fashion choice is … well, your choice, and it’s a matter of taste.  At that point:  pull yourself up a little taller, and wear it with pride.

Readers, what are your thoughts?