In addition to their sale section, Lands' End Canvas sometimes has this weird "classifieds" section where you can get extra discounts on a small selection of items.
Right now they are offering some pants and sweaters and the prices keep dropping throughout the course of the week. The goal is to wait til Friday when things are 75% off, but then again what you want might be sold out by then.
Here are the pieces I have my eye on in case they are still around on the super cheap day:
Draping shawl collar sweater (originally $89.50, now $30.50)
The belt they have this with is all wrong, but you can use whatever belt you want (or none!) and a more fun shirt underneath.
Plaid and leather belt (originally $79.50, now $20.50)
E would love this. And wear it with mismatched plaid shirts and pants. But a sane person would use it as an accent to gray pants or to cinch an oversized white shirt.
Plaid winter shorts (originally $59.50, now $20.50)
Don't wear these wool shorts with the belt above, but they are fun over tights with a button down or slouchy sweater.