Nobody really likes a sweater vest, except for all girls. And since boys really like girls, we may wear one every now and again.
The hope is that we can wear one without looking like these guys....
Here are some simple rules.
1) A pig in a sweater vest still looks like a pig.
I wish I had an image for this, but my demo version of photoshop just run out. The point is that if you wear a crappy shirt and a crappy pair of pants and then throw a sweater vest over the top your just going to look like a guy in crappy clothes and a sweater vest. Go for modern, well-fitted, pressed pants. As for your shirt, remember that you are pushing the envelop with the vest so make sure your shirt is as solidly cool of a shirt as possible.
In short start with a cool outfit and add the sweater vest. Don't try to make the vest carry the weight of the outfit.
2) Roll up the sleeves 2 turns.
When pulling off a slightly dorky item, add a little grit to the piece. You don't have to steam punk yourself and roll it up to your biceps with a hard pack of cigarettes imbedded. But try to give the look a little street cred.
3) Let something Pop. 1 out of 3 ain't bad.
I once tried to play a show wearing my favorite cool hat, my favorite cool coat, my favorite cool boots, my favorite cool pants and my favorite cool tie.. My then girlfriend, Dee from Sunny in Philadelphia, said, and I quote "you just made everything less cool" She was right!
With colors and with the patterns,let 2 of the 3 things be neutral and pop one of them. i.e. plain tie, plain shirt, patterned vest. Or plain, vest plain, shirt patterned tie.
4) Stay Earthy
Earth tones are understated and work really well together, especially in the fall. Browns, greens, bieges, even some grays. Tweeds, wools, herringbones... Wearing a vest and/or a bowtie is a small step towards the obnoxious side of the style spectrum, it is your responsibility to balance that move back to the cool end by wearing understated fabrics and color pallets. You come out on top when you take the risk but you execute it properly.
5) Bedhead those tails
Bedhead is an interesting hair product. Its purpose is to make your hair look stylish by making it look like you just woke up...but with really cool hair. Its bizarre that we all love that intentionally messy look, but we do! So untuck that shirt, let those tails hangout. Not in an ugly way, but in an intentional way that says you are casual and not that you are a slob. Its a fine line. Find it.