I tend to associate boots as something to be worn in Fall and Winter. However, they are just as good as a transition piece for spring. By wearing layers and colors, you can still acknowledge the colder weather by wearing your boots. They’re also better for the rainy days we experience in March and April than regular shoes. Here’s a good example.
Also, if you’re skinny like this guy, you can get away with slimmer jeans. His don’t look painted on, but they’re slimmer than most. They’re current but not bad enough he’ll be embarrassed in five years.