Good eye, Houndstooth! The chair is a Philadelphia Chippendale mahogany easy chair (mid- to late- 18th Century). My wife's grandmother had the superb good sense to start collecting Early American furniture back in the late 1950s when it was woefully undervalued. As luck would have it a few pieces made their way down to us. The red damask fabric is old but certainly not original.
As to the boots, I'm really pleased with these. They are vintage Testoni, originally made for a men's store called Erve in Nyon, Switzerland (a twon on Lake Geneva; I had to look). I found them in the thrift store, tucked away among the womens shoes; not my size, but I couldn't pass them up. They are by far the nicest Testonis I've seen. I would guess they were made in the 1970s. They don't show the usual Testoni cloth label; rather all of the information and the Testoni crest are embossed in gold on the liner. The quality of the leather is absolutely superb. The design highlights are the chiselled toe, the single-eyelet strap, the heavy brushed gold buckle, and the slightly stacked heel.
They would mesh well, I think, with things from this Japanese shop:www.sinner.jp