Great advice from notenoughhangers. I also put a pocket square in the chest pocket of my vest, if it has one. It’s a nice touch.
I remember how self-conscious I was to the idea the first time I considered wearing a vest. I really didn’t really know how to wear it or what to put with it. It seemed similar to a cardigan…but without sleeves. Or maybe a sport coat…but without sleeves. Once I pushed my insecurities aside, put the credit card through, and started to play around with the items I already had in my wardrobe, I noticed that the traits of the vest that I was most scared of—the overall ambiguity of the garment—suddenly became its best features.
I guess I didn’t go about buying my first vest, in blackwatch plaid, very wisely. Although I absolutely love my vest, and I get a lot of use out of it, I would recommend buying for your first one something in a more neutral color—maybe in grey, like the one Justin Timberlake is wearing in an issue of GQ a while back. Navy blue or khaki could also work, but I feel like grey lends itself to the greatest versatility. One thing that I don’t regret about my first vest is the way that it fits—really snugly. I can feel the sides of the vest against my torso. An ill-fitting vest will be exposed around the arm holes, where extra fabric will pull away from the body, creating a sloppy overall look.
So, once you’ve gotten your well-fitting, neutral colored, vest, what do you pair with it? Much like a cardigan, its range of versatility is almost endless. I have done everything from wearing it with a tshirt and jeans to under a sport coat with a tie. I especially love the way it’s styled on Justin Timberlake—with a black leather jacket—creating a very rugged/polished look. Also, as a side note, don’t button all the buttons on a vest. Leave at least the topmost and bottommost ones unbuttoned.
One thing that I like to do when trying to dress up the look is put a pocket square in the top left pocket of the vest. It adds a little extra color and pattern, while adding an element of the unexpected. It’s a traditional finishing touch of a more formal look placed in a more untraditional spot.
I feel like the vest is generally seen as a part of a larger look, namely a three piece suit, and through that association we link the vest with formality, and we feel a little uneasy at the thought of wearing it alone. If you just think of it like a cardigan—really, I cannot think of an instance in which one could not switch out a cardigan for a vest—you’ll be able to see that the vest is an incredible stand alone piece which, if it is the only purchase you make this season, can easily rejuvenate anybody’s wardrobe.