My favorite odd jacket for this or any fall/winter season is a gray tweed herringbone jacket. I have had one for about 2 or 3 years now and love when the weather turns cold enough to wear it. It is the perfect jacket for jeans, chinos or accessory for your normal work slacks (black, navy or heather gray work best from a color stand point).
The jacket is sophisticated casual. It has a very English countryman heritage so it has the old elegant sophistication that comes with such a heritage. Historically this jacket would have leather elbow patches for hunters. Hence the jackets heritage is casual, due to this it is typically made only as an odd jacket. (But I would highly encourage making a slim fit tweed herringbone suit with bit 2 inch cuffs on the pants, but that is my personal style and not something everyone can pull off.)
This season stick with a beautifully tailored slim fit gray herringbone tweed.
Rugby (by Ralph Lauren) has my favorite version of the jacket this season (top picture). Rugby makes a very casual, cool and aggressive version of the jacket with details like: stitched patches instead of the English style leather elbow patches, colored lining under the lapels and a hidden stitched skull and crossbones under the left lapel. Fashion is often in the subtle details and Rugby nailed it with this version of the jacket ($350 or so).
Theory &
JCrew both have more traditional but modern versions of the jacket, so you will not have to worry about looking like your Grandpa, but you can still look hip on your date (JCrew & Theory pictured above: JCrew has the tie).
Uniqlo also has a version of the jacket that will be coming out in the next month or so, this might be the best financial option as long as you live in New York or have a friend in New York who can ship it to you (Uniqlo only has one store in the US, in New York, and they don't take online orders).
Rock the tweed herringbone as one of your go-to-jackets, this fall. Leave the leather jacket at home and instead rock the herringbone, it will keep you just as warm and you will have classic and sophisticated alternative to leather. The ladies & the fashionably aware men will appreciate your sartorial decision.
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