Something I quite liked to do this fall was to wear my loafers with soft-textured socks. This particular September look is an example of that, pairing super-soft olive wool socks with tan calf loafers. In other areas is pretty much regular weekend sport coat stuff - soft tailored lines and quality fabrics.
The jacket is from L.B.M. 1911, grey gingham check shirt from Barba Napoli, untagged olive cashmere knit tie, Drake's pocket square, braided Valchetta leather belt from Berg & Berg, bespoke trousers from Harrisons of Edinburgh fabric, olive bridseye wool fabric socks from Pantherella and tan calf tassel loafers from Septieme Largeur.
A moleskin jacket in a fairly neutral color is a great choice for any casual fall or winter outfit. Dark green like mine is also a very versatile jacket that can be paired up with a variety of accessories.
Pretty much the perfect fit for this look in my opinion, this Drake's pocket square combines rust, olive, mustard, white, aqua and blue colors.