In terms of shirts and suits I basically find it safe and easy to stay with staple and plain, conservative colors such as light blue and white in shirts, blue and grey in suits. For example during fall and winter, most of my “suit days” I’m wearing plain grey flannel or dark navy wool.
That being said, lately I’ve been having bigger and bigger interest in a bit more boldly patterned sport coats (actually three of my latest sport coat purchases have been just in this category) and there’s no end visible in terms of that interest.
Some say boldly patterned sport coats are actually the one of only areas where men can be safely daring. On the other hand a little bit of boldness can help you making a simple tailored jacket a lot more versatile, and as long the design is traditional and the you keep the color of the jacket fairly conservative, you should be able to wear your jacket without making yourself looking snobbish.
When it comes to the league of patterned jackets, Japanese Ring Jacket is definitely one of the best players on the field. Bold but flowing implementations of classic combinations.
Checked sport coat - How to play with patterns
First of all I guess there’s no “rules” of wearing sport coats with patterned fabrics but in general I’d say that the bigger, bold and vivid the pattern - the smaller is the potential for the jacket being used in formal or business oriented combinations. And if you’re heading to a bit more casual event, a sport coat with light windowpane or a PoW can make your outfit to be “dressed up” enough without making you look overdressed.
Second point to pay attention is the way you accessorize when using a jacket with bolder patterns. In case one is wearing multiple patterns, varying the scale is probably the easiest way to ensure that nothing clashes even though the scaling also depends on the fact how many different patterns you are wearing. I personally try to keep the amount of different patterns in one outfits always under four. If the jacket I’m wearing is featuring a heavy and strongly visible checks for example I prefer having the other parts as plain as possible.
Checks doesn’t have to (and shouldn’t) be all “screeming” and distinguish. Perfect example here by No Man Walks Alone as the plain shirt and tie underlines the subtle pattern and color of the Cantarelli gun club check jacket.
Very bold and fine looking, lightweight wool db-jacket made by Italian G.Abo - worn here by Adam of Spiga 3.
I might be biased (and I might drop that bag) but in all it’s simplicity this is a 5/5 fall casual-look.
Conclusion - 5x Checked sport coat
And finally 5 DLA-choices to get your game going.
Blue wool blazer with a subtle windowpane is a safe bet and easy choice when entering the world of patterned jackets.
Cotton-wool mixture and small checks from the “flying” line of Italian Tombolini.
The one on the list that takes maybe the most to pull off but the green color and perfectly matched PoW check makes this a perfect fall blazer.
With this wool-cashmere blend Havana fit jacket which is featuring a bold rustic check pattern Suitsupply offers a price worthy option also in this category.Lardini - Houndstooth
Not really checks, but this double-breasted houndstooth patterned wool jacket, even though featuring three patch pockets is suitable not just for casual Fridays but also in more dressed-up combinations.