Olathe T-Shirt

Firstly, it is hard to locate three t-shirts, looks as an underline. Maybe make a white, then navy and red? Secondly, trophy itself a bit large and needs to be in different shape. Thirdly, " T " in " t-shirt " can be done as a t-shirt(s) and you might not need a symbol above, only text. I like font and colors at the moment.

NOPE. too many elements going on there. looks tidy enough but there's too many shapes and too complex. You can try what felix suggested , would be a nice play if you do it proprer. The font in the current context leaves me an impression of early 90 and not in a good way. If you want to keep anything from the old logo (style and elements) you got to do it in a coherent way.
I would make Olathe all caps with a serif , demi bold, stylish and pretty oranted , add in subtext t-shirts and trophee, and put only one t-shirt on top (minimal as possible).

To add to what others said, I must say this: just because a design is familiar doesn't mean it should be rehashed in its future versions. Yes, you want recognition, but it's not that hard for people to adjust to something new. You're not going to lose a customer base because it's too foreign. Don't be afraid to venture into something different. It's your job as a designer to make decisions for the client, not the other way around. Decide what is good about the old version, and transfer them over.

A lot of modern logos that were redesigned keep the same properties of old logos, but not always.

http://fineprintnyc.com/images/blog/history-of-apple-logo/apple-logo-1.jpg

I just wanted to drive this particular point home because a lot of the time, designers are trapped by a certain constraint placed by the client, and usually it inhibits potential.