I have Wino Slip Cup and I went TTS. They fit well in TTS but I can see them loosening up enough over time where maybe going 0.5 down would work.
I personally suggest folks go TTS and combine with either thicker socks and/or swapping the insole with something a little thicker to accommodate any stretching over time.
The Winoa with an insole swap both optimizes the comfort, but also the fit (if needed), and the support. I run STI insoles in my Gamma G6 and it's perfect, so Wino would also be solid!