Originally Posted by Luc-Emmanuel
Anything but monkstraps! The buckle will show and keep the pants from laying right.
You also need to hem your pants quite high. You're looking for a "no break" with narrow opening pants, especially if your shoes are already riding high on the ankle.
When I asked my tailor today to show me what it would look like to have no break, he showed me that because the opening is narrow it would have to be cut really high for their to be no break - so that basically in the back the pants are coming up to almost the top of my shoe (it's hard to explain, but a wider bottom pant can be cut lower and still have less of a break because the front of your foot is lower to the ground than your instep is). So, I had him cut the pants so that they are about .5 inch up from where the sole of my shoe starts as a kind of compromise between having it not break too much in the front and having it not be too high in the back. We'll see how it turns out.
Originally Posted by whoopee
Chelsea boots also work well, as they continue the line from trouser bottoms to high vamp.
Now this seems like a very interesting suggestion. I'm definitely going to have to give this a try.