I've scoured Pinterest for HOURS (days, maybe even weeks) looking for inspirational Engagement Session outfits. I've blog-stalked and had numerous discussions about locations, looks, and styles with my sister, the photographer, and of course Jay (who thinks I'm completely insane).
I look at other peoples engagment sessions that I love and I pin it. When I find a cute outfit I like, I try to figure out how to make Jay coordinate with me but not "matchy matchy"
The best advice I got was: DON'T Match.
Do not both wear variations of the exact same outfit or you run the risk of ending up on this amazing site. (you're welcome for this gem)
The 2nd best advice was: Don't wear something that you won't ever wear again. Look like yourselves. Avoid trends that you wouldn't normally wear or you'll just look silly and like you're trying too hard.
(like these people)
The 3rd thing: have your pictures taken at a spot that you've actually been or will go again. Seeing your beer-only friend trying to pull off pics at a winery is almost as good as seeing your tom-boy sister making out with her future-hubby in a sequin dress with weird back-lighting.
You want your friends and family to say how cute the pictures are, not be asking themselves "what the hell were they thinking?"