FileConstraints.java

import java.io.File;
import java.lang.annotation.Annotation;

public class FileConstraints {

    {
        final Mapper mapper = new Mapper();
        mapper.map(Executable.class, File.class, File::canExecute);
        mapper.map(Writable.class, File.class, File::canWrite);
        mapper.map(Readable.class, File.class, File::canRead);
        mapper.map(Directory.class, File.class, File::isDirectory);
        mapper.map(Exists.class, File.class, File::exists);

    }

    public static class Mapper {
        public <A extends Annotation, T> void map(Class<A> a, Class<T> type, Constraint<T> constraint) {

        }

        public <A extends Annotation, T> void map2(Class<A> a, Constraint<T> constraint) {

        }
    }

    public interface Constraint <T> {
        public boolean isValid(final T value);
    }
}