If I can pack for 5 nights in Chicago in a carry on every New Year's, I can certainly pack for a long weekend at WDW in Orlando in a carry on! Ha! I was so happy when the kids were old enough and we could skip baggage claim.
I am not the packing queen, but it can be done. Especially at WDW where you can do laundry at any resort if you *have* to. I always bring two pairs of shoes - one pair I wear on the plane, one pair in the carry on. Then I decide on every outfit to go with those 2 pairs of shoes. (You typically have 2 pairs of practical shoes you wear nearly all the time anyway - WDW isn't the time for your 'fun' shoes you only wear once a month that only go with that *one* oufit.)

Sometimes I have to cram in 2 pairs of shoes if I'm going to a fancy dinner or award ceremony, that makes things a little more difficult, but that's rarely a problem at WDW for me.
Next I decide on one outfit for each day - long weekend usually only means 3 or 4 tops and 3 or 4 pants (or if you're like me - a dress.) Toiletries are difficult. I put one 3 oz bottle of shampoo in both my husband's and my bag. Same for conditioner, although sometimes I need more conditioner, since I have more hair.

My hubby is always kind enough to not use the conditioner (shampoo only) until we are sure I'll have enough to last the whole trip. Doesn't make much of a difference to him, but makes a world of difference to me! The hardest toiletries for me are things like facial lotions, etc that are larger than 3 oz in their original packaging. I have to plan ahead and buy smaller bottles to transfer those items to for the trip. At this point, I have pretty much every bottle I need, but I do sometimes have to buy new ones when I switch products, etc. I bring 3 oz of liquid dish detergent to wash our refillable mugs and sometimes 3 oz of laundry detergent to do laundry (although you can buy laundry soap in the laundry rooms, so I rarely do this now unless I have to.....)
I will admit, if I don't do laundry, what I wear home from the trip can sometimes be pretty funny. I think on the way home last month I was wearing black leggings, a giant tshirt and a huge sweatshirt. I had worn all my nice dresses in the parks. Oh, well - at least I was comfortable!
Packing for my kids is even easier. I never pack for my husband, so I'm no help there.
That's all I've got. Good luck! You can do it!

