Autumn is the best season for the classical dresser. The onset of cooler temperatures permit heavier fabrics, structured jackets and tailored overcoats. Most pairs of penny loafers will now be given a rest after a season of use through the summer, while dependable brown suede tassel loafers like Crockett & Jones’s iconic Cavendish model can be worn almost all year round – unless is rains or snows heavily. I have seen English friends wearing them with knitted wool socks on chilly November days.
Regardless, some shoes are better suited to autumnal dressing than others, and rugged designs with Country or Scotch Grain upper leathers, sturdy welted constructions and rubber City Soles are well placed to adapt to the different kinds of weathers that come with fall.
My favourite autumnal outfits tend to revolve around the classic English combination of a sports jacket made in heavy tweed, paired with soft corduroy trousers. The most versatile shirt to match almost any kind of tweed and colour cord is made from light blue cotton Oxford cloth, although checked shirts in various colours are wonderful in fall too.
In town, I find that classic brown calf’s leather Oxford shoes like the Connaught II are perfect with a tweed jacket and corduroy trousers, and on the weekends or in the country Jodhpur boots like C&J’s Cottesmore are a dependable choice. If you replace the corduroy trousers with a pair of grey flannels, your outfit will look a little more formal, resulting in a very smart pairing with mid-brown Oxfords. For a more casual look, dark jeans and a tweed sports coat look great with the Jodhpur boots.
When it comes to formalwear, a grey glencheck double-breasted suit is my favourite piece to wear during the cooler months. No wardrobe is complete without it. I wear this type of suit with dark brown shoes nine times out of ten, although it also works well with polished black shoes. Try a checked suit with a pair of traditional brown brogues like Westgate II, or with contemporary black tassel loafers like Cavendish.
Now it’s cooling down, you should spend some time thinking about outerwear. I recommend either a dark green Loden coat (Loden coats are traditional Austrian walking coats, cut in dense showerproof woollen cloth) or a reversible raincoat (one side tweed, the other side cotton gabardine). These two coats looks great both with tweed jackets or glencheck suits alike, as well as your mid-brown Oxfords and Jodhpur boots.
Let me end with one final piece of advice. When I choose suits or odd trousers, I always think of the shoes that I’d like to wear with them. In autumn, ankle boots should be worn with narrower and shorter trousers because they show a touch more of each boot. Longer and wider trousers might even get caught in the boots’ speed hooks – never a good look. If I want a suit that’s versatile enough to wear with both Boots, Oxfords or Loafers, I choose trousers that are slightly narrower at the hems for this reason.
As always, in menswear it’s important to pay attention to the details. Nevertheless, the classic pieces mentioned here are a good place to start; a tweed jacket, corduroy trousers, a glencheck suit and understated grey flannels will see you through the autumn season and beyond, and complement your Crockett & Jones shoes too.