What are the most useful odd jackets for someone who doesn't have to wear classic menswear in the first place? Let's say a thirty-something who works in an office where he might dress up a bit but a suit looks eccentric and chalkstripe flannel looks like someone's been raiding the dress-up box. He gets bored of wearing designer cardigans and jeans with chukkas every day and dons an odd jacket and trousers every now and then. Which? Our man is of middling income and circumstances and goes to a wide variety of different events. He doesn't need to own black tie; few people do. Other than for weddings, he may not even need to own a suit. He's certainly going to find himself sitting in wet grass or having his toes stepped on by strangers from time to time. But he has enough spare cash to buy unfinished trousers and have them pressed.
1) Dark blue hopsack or even worsted flannel, half-lined. Neither old man navy nor any shade of estate agent; just blue enough to be perceptibly blue at a distance. SB, patch pockets. Horn or MOP for the buttons (brass and gold are far too "in the navy" for our man). Could even be part of a blazer suit and double up for summer and spring weddings.
To be worn with: probably khakis. Cream drill is going to look too dandy.
2) Blue herringbone. This is our man's dressier jacket for autumn/winter. Same styling as his spring/summer blazer (except no MOP).
To be worn with: I'd like to say light grey flannel but only men who poast about 2" cuffs actually wear those. Cords in any traditional colour bar green are about the best that can be hoped for here.
3) Dark chocolate cord. The only style of casual jacket that doesn't have English country house connotations allows our man to transition into a more SW&D mode as shires staples like check tweed and donegal are kryptonite to looking even vaguely 'street'.
To be worn with: raw denim.
4) Blue linen, buggy lined. Has to be the right shade of blue. This is his one truly seasonal jacket. Same styling as the first two.
To be worn with: white denim. Yep - white jeans, even ASW is down with them these days. Madras shorts or nantucket reds if he's a bit of an eccentric anyway.
Controversial 5) Black hopsack. 1 button PL. Having gained a reputation as something of a snappy dressier for wearing the above, his friends are going to expect our man to look good in the club (which he's still young enough to be going to). Hopsack for obvious reasons. Black because it's the only colour of jacket that doesn't look like a) he's confused about how to dress for a club (brown, green, tan etc.) b) he took his tie off as he was getting on the tube at Canary Wharf.
To be worn with: legs are invisible anyway under the strobe lights.
General conclusion: outside of #menswear, solid blue jackets may be the future. Autumnal colours are just too heavily country club connoted to work outside of a full classic menswear look.
Jackets our man doesn't wear:
Lt Cdr (ret.) blazers
Lovat in any fabric (looks too LL Bean catalogue for his mainly SW&D friends)
Tobacco linen (too #menswear)
Cream linen (absolutely not)
Brown donegal (sadly - for the same reason as lovat)
Gun check (this should exclusively be worn by men who own a great number of #soporific jackets to make fun of the fact they own a great number of such jackets; our man owns very few or none)
Charcoal in any fabric (too difficult given his limited selection of dress trousers)
Light grey in any fabric ('Northern Lights' reserved for seasoned poasters who can take the flak)
A more muted check/plaid (probably blue)
Edited by Marsay - 9/24/16 at 4:32pm