Lake Oswego catches attention when you drive through it on Interstate 5 because it usually means that you're almost to Portland, and this drive is nearly over. That's the outsider's view.
From the inside, Lake Oswego is more confusing than the human genome. It seems like there's a cul-de-sac every time you turn, and when you turn back, the street you came in on has magically become a cul-de-sac. Good luck getting out of here. Every house looks exactly the same; but to their credit, the insides are quite luxurious. You could imagine that someone like David Spade keeps a house here.
The downtown center, if you somehow stumble upon it, is cute. It has a bunch of small local shops, and it makes it appear that perhaps this place has a soul. Don't believe that's the case, but the area is nice.
Bridgeport Village, the gigantic outdoor mall off of I-5, is the same homogeneous nationwide crap you'll get a few miles north in Beaverton at Washington Square. It's notable mostly for its IMAX screen - the only one in Oregon that shows Hollywood movies on a consistent basis. This is a vast counterpoint to the constant nature documentaries at OMSI.
This place isn't worth a long side trip, but it's not bad if you want to check out where the rich people live in the Portland Metro Area.