I also travel with a carry-on that usually has the following:
1 pair of slacks
1 skirt
1 dress (may substitute with another pair of slacks)
1 pair of jeans
3 pairs of workout tights/pants (one worn on plane)
4 work tops
2 "casual" tops
2 sweaters
1 hoodie (worn on plane)
5 workout tops (1 worn on plane - I also use these to sleep in with panties)
3 sports bras
1 pair of pumps, usually in a punchy color (this week is burgundy, last week was dove grey) and I make the rest of my wardrobe a "capsule" to work with the heels, bag I bring and scarf
1 pair of comfortable walking shoes (usually moccasins or Sanuks - worn on plane)
1 computer bag & computer
1 scarf
1 pair gloves
1 pair of flip flops
1 coat
1 collapsible tote which scrunches up into a purse
Panties and bras needed for outfits
This changes based upon the city I'm going to - my bag for Philly looks very different vs. my current travel bag for NY. As it continues to cool down the workout clothes will pretty much disappear and I will start just walking the city for exercise - the flip flops will stay at home and some knee high riding boots will be worn on the plane.
PS I know it sounds like a lot to cram everything in one suitcase (my boarding tote is full of medications, books, papers, etc.) but space bags are a lifesaver.