It's not hard if you follow some basic rules.
The first one is: NO denim! It is heavy, bulky, does not keep you warm, and takes forever to dry when washed. The only reason you should ever want to take denim when travelling is if you are planning to spend time on a farm doing outdoor work/riding. Bring lightweight trousers and a pair of very thin long underwear for any really cold nights (and yes, Orlando can get cold, particularly when it rains, which it often does that time of year.)
Rule 2 is: Pack no more than one pair of shoes, and preferably none. If you can make do with the ones you are wearing to travel in, that's best of all.
If you pack fleece for any reason, compress it in space bags. (Better to wear it to travel, IMO. Layers, instead of a heavy coat. I find that a fleece covered by a windbreaker -- plus gloves and long underwear -- is enough for the cold spells I've encountered in Orlando.)
If you really must have shorts, take convertible zip-off trousers. They do double-duty. (Bass Pro Shop has a value-priced selection for the entire family.)
Be ruthless when packing toiletries/makeup and take only what you absolutely must have, in tiny containers that fit in the 3-1-1 baggie. Use hotel shampoo/soap if at all possible; it is only for a few days.