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My photographer told us to have two outfits: one that was something we'd wear everyday (like jeans and a t-shirt or something) and something that was a little more flowy, like a dress or skirt for me or a loose button-down shirt for him.
Your engagement photos are a reflection of you as a couple, so I would definitely wear something that is you and not just something you think will look good in photos.
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oh fun! i am also doing my engagement pics this weekend! I am wearing an informal white cotten dress for day pics (my FH is wearing a button down long light blue shirt & brown pants) for night, i have a dressy white shirt with nice jeans, and fh is wearing a nice button down with jeans. we're going for a style that is a more refined polished version of us.
imo you would want to wear what style is comfortable for you so that you would look natural in the photos. they are your pics, so you should wear what you want!
have fun! 
I think what you described sounds great! The skirt would have fun movement for pictures, and not look out of place agains the backdrops you describe. I saw a couple getting their engagement pics taken in a historic neighborhood near me last weekend, and the girl was wearing a cocktail dress while the guy had on jeans and a blazer. They were a super-attractive couple, but the poor girl was FREEZING as it was a very breezy day. So my advice would be to make sure you are comfortable and weather-appropriate, as well as photogenic :D
Definitely wear whatever you're comfortable in. :-) If it helps though, keep in mind that patterns can distract the viewer from the subject (your beautiful faces). Since solids are more neutral, the picture tends to focus on you two more. Just a suggestion :-)
And do keep in mind the weather. I wore a bright red wool coat for ours and it was much easier to be comfortable outside in January than if I'd been in a skirt or tshirt. Have fun!
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I agree with MissV, wear what you are comfortable in. I would stay away from clothing that may seem "too busy" (lots of detail etc.). Because it really does take away from the picture. I do a bit of amateur photography and always suggest my clients to wear solid colors with nothing too busy.
At the suggestion of my photographer, I am going to glam it up a bit. Here is my dress and I will be wearing a birdcage veil. I am not going to post the veil because I haven't bought it yet and things posted on this site tend to sell out quickly! I haven't decided if I will bring a change of more casual clothes.
I wore a black dress with a cinched belt at the waist and tall heels and it worked out well because we were able to get some very nice black and white photos from it. My FI wore a shirt, tie and slacks. . .
You definately don't have to match, but you should pick outfits that go together. Maybe both in similar color pants (or his pants and your skirt similar in color) and tops in complementary colors. The reason for your photographer's recommendation is that you really want to be able to focus on the two of you. If you wear a busy print, or really bright colors, then that is what stands out in the portrait - your clothes, not you.
I would never wear the same style of shirt (both black polos, as you said). For one, we are not the kind of couple who dresses alike - a little too cutesy for us. For another, I think those kinds of photos end up looking as if people were required to wear a "uniform." Better to have everybody in a different style of shirt but colors on a theme. For ours, FI wore charcoal slacks and a navy sweater. I wore black corduroys and a cranberry colored sweater.
I would hesitate to have you both in mostly black, just because it seems a little somber for an engagement portrait.
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Our engagement session is this Saturday, and I don't know what to wear:)
Our photographer said many couples wear matching outfits, like white button downs with jeans, or black polos with jeans. That is not our style at all...we're a little retro...and I don't want to wear jeans. Or matching outfits.
My honey wants to wear a black guayabera with jeans and black dress shoes. I have a long, swingy gypsy skirt that might look good, but I usually wear it with a t-shirt and a black corset belt...which might be a little too funky for pictures?
We will be shooting in our inner city neighborhood at some of our favorite spots, like the park, the paleteria (an ice cream shop) and a grafitti wall...
Any suggestions (or pictures of any non traditional outfits you wore for your engagement pics) would be VERY helpful! Also, how many outfits are you supposed to take???