The trophy can be earned during The Madonna of Sasau after Johanka's speech on the rock outside of Sasau where you fight off the villagers.
The requirements are as follows:
Kill Runt
Complete the Baptism of Fire main quest.
Kill Other People
I failed this requirement with 17 kills (15 enemies). I killed 11 innocents in Samopesh in order to trigger the conversation options with Johanka.
Sleep with Lady Stephanie
Put on the shirt at the end of At Your Service, My Lady side quest.
Sleep with Bath Wenches
Visit any of the bathhouses and pay for a wench.
Steal and Get Caught
Steal food from one of the food vendors and surrender.
Go to Jail
Can be combined with stealing or killing. I did both just to be safe.
Get Drunk
Drink alcohol until drunk. To be safe, make sure the second stage debuff activates, not just the first stage buff.
I also had the following debuffs and buff active when I spoke with Johanka. The conversation options for sleeping with the wenches would not trigger without them.
1. Alcoholism debuff
2. Drunkenness debuff
3. Released prisoner debuff
4. Alpha male buff
The trophy should pop during the early part of the conversation with Johanka.