The clothing question depends entirely on the specific facility. Every institution has its own rules about personal clothing. Some places issue uniforms from the start and your clothes get bagged and stored until release. Others allow inmates to keep certain personal clothing items like plain underwear or basic jeans that family can send in later. There is no universal answer until you know where you are going to do your time. Once your facility is confirmed, you can call directly or look up their specific intake rules.
On the money, yes, bring a money order made out to yourself when you report. Give it to the processing officer during intake and they will issue you a receipt and apply it to your commissary account. Arriving with money on your books right away means you can start buying necessities at your first commissary visit rather than waiting for your family to figure out the deposit system.
One year is going to feel different on day one than it will looking back on it from the other side. Getting oriented quickly, finding a routine, and staying focused on what comes after make the time manageable. If you have any specific questions about what to expect at the facility you are assigned to, InmateAid can help once you know the location.