I own three blazers - standard black, gray with pinstripes, and tan with white trim. All three are pretty standard and season appropriate to take me throughout the year. Except for at least THREE years, I had trouble wearing the last two, and to be honest, wasn't even that good at wearing the black one, which should just be easy!
This year, since I have been working so hard to curate my closet, decided to work really hard at incorporating them into my wardrobe, before making the decision of whether or not to let them go.
Since it's summer, I started with the tan one and just really, haphazardly put it on, on the way out the door. It worked! Now, instead of a cardigan, I grab this blazer, and I've been able to wear it regularly since - without having to strain my brain on how to make it look good.
This gray pinstripe one was actually purchased before the tan one and it sat in my closet waiting to be worn. That day finally came a couple weeks ago when I, for whatever reason, I don't know, decided to throw it on. And it also worked!
I think in order for me to make blazers work, I have to actually give it NO THOUGHT whatsoever, and treat them as outerwear instead of something that is supposed to match. I mean, it should match what you're wearing but I think because the idea of a blazer having matching bottoms was so ingrained in my head, I tried TOO hard, to make it match what I was wearing on the bottom, even though I purposely didn't buy a matching bottom. That idea was just acting like a roadblock and once I kicked it to the curb, found many occasions to wear it.
I also don't think I'm one to wear a matching pant/skirt & jacket suit, with the exception of black (but only because of necessity).
That said, I don't recommend buying a black pant/skirt & jacket separately because the shades have to be just right. I didn't buy my black blazer with matching bottoms and now regret this. I have been searching for the perfect set.
Something that I thought was a good suggestion - I read somewhere that you should always take you blazer and bottoms to be dry-cleaned at the same time so the black can always fade at the same time.