No doubt it's getting colder. But cold enough for sleeves on a jacket? Only you can answer that bold style choice. If you are going to layer a vest over a shirt, there are a few things to consider.
First, never wear a vest over a tee shirt unless you're staring in an 80's action film. Sorry I'm not sorry.
Once you aren't doing that, be careful of the shirt you're laying the vest over. I've never been a fan of layering a vest with plaid. You look like fucking Macgruber. To be clear, Will Forte dresses like this facetiously.
Honestly, wearing a vest over a single layer is a risky style maneuver. What I like about it (when it's done correctly, like above), is that it brings a rough, outdoorsy feel to an urban environment (instead of going full hipster urban lumberjack...just so we are clear, this isn't what you want).
- Wool socks are great.
- Don't be too stereotypical with how you wear your vest.
- Avoid looking like Macgruber.