The Guide to Pant Length and Shoe Pairings
Fashion is about wearing what you love in the same way language is about conveying your message: the better you use existing vocabulary and grammar, the clearer you will be. Fashion rules at their best only help you communicate what you love and who you are.
I think we share too few clear fashion rules, actually, so it's a special joy to discuss pant hems and heels. Here, we borrow the definitive conventions from classic men's tailoring but adapt them to the wider, more diverse world of womenswear.
Let’s work backwards from the shoes to sort out the right hem length, and then you'll have a framework to choose shoes for your pants. It's so helpful to think about which pair of shoes you'd wear with a pair of pants when you're deciding whether to buy them or hem them.
High Heels
The cords on the left hover way above the toe box, while the jeans on the right go all the way down to the top of the toe box. We get one long line from the waist all the way down to the toes.
This image of the silhouettes will show the awkward hovering of the cords:
The hem length affects how the whole pant hangs, not just the very bottom.
Next, let's look at a hem that's too long.
Flats
On the left, the puddles of denim below the ankle are a sign that these jeans are too long for the loafers. This look is comically too long, though. What about a fold right below at the ankle?