Check that a jacket really fits over your layers
Try a jacket over what you will wear outside, including the thickest likely midlayer. A jacket can fit over a tee and become uncomfortable over a knit. The place to check is the shoulder, upper arm and fastening, especially if you will also carry a bag.
Put the full combination on
Use a grey knit and dark jacket like the photographed pairing, or choose the equivalents you own. Close the jacket, then cross your arms and reach forward. If it pulls across the back or binds at the elbows, change the midlayer or choose a roomier jacket. Check whether the cuffs of the inner layer bunch under the sleeve. A thinner knit may be enough in mild weather; use more protection if the forecast calls for it.
Check the bag and the seat
Put your bag on and try the movement you will use most, such as reaching for a rail or carrying a laptop. Then sit and see whether the jacket pushes up at the neck or rides tightly across your lap. A long layer can be comfortable standing but awkward in a tight seat. Remove it indoors if you have somewhere to put it.
Name the combination in your wardrobe
Save the jacket and the knit that actually work together, and record which layer you remove indoors. If the jacket only works with the thin version, keep that as its own outfit. You will know exactly what to reach for on a similar day.