Continuing with the experiment, I also swapped for a different belt a la Emma Watson for Burberry S/S 2010. As luck would have it, the width of the belt fits perfectly through the trench's belt loops and gives the outfit just a touch of military vibe.
For next time, I think I'll match the number of buttons down the front of the trench. It's not as noticeable at an angle, but from a frontal view, 4 on the left vs. 1 on the right does look a bit odd.
Trench wearers, do you have any other tips or suggestions for me to try?
dress: Express (similar)
belt: Madewell New England stripe (similar)
ring: Forever 21 textured horse shoe (similar)
wedges: Nine West Smooch (sold here)