Starting Kotlin 1.3.70 and 1.4, this should be possible setting a specific compiler option: https://kotlinlang.org/docs/reference/whatsnew14.html#type-annotations-in-the-jvm-bytecode .
On any previous version or any situation where this support is not sufficient, you have to write a custom validator.
Example one for validating that a collection only contains hex strings:
@Target(
    AnnotationTarget.FUNCTION,
    AnnotationTarget.PROPERTY_GETTER,
    AnnotationTarget.PROPERTY_SETTER,
    AnnotationTarget.FIELD,
    AnnotationTarget.ANNOTATION_CLASS,
    AnnotationTarget.CONSTRUCTOR,
    AnnotationTarget.VALUE_PARAMETER
)
@Retention(AnnotationRetention.RUNTIME)
@MustBeDocumented
@Constraint(validatedBy = [HexStringElementsValidator::class])
annotation class HexStringElements(
    val message: String = "must only contain hex values",
    val groups: Array<KClass<*>> = [],
    val payload: Array<KClass<out Any>> = []
)
class HexStringElementsValidator : ConstraintValidator<HexStringElements, Collection<Any>> {
    companion object {
        val pattern = "^[a-fA-F0-9]+\$".toRegex()
    }
    override fun isValid(value: Collection<Any>?, context: ConstraintValidatorContext?) =
        value == null || value.all { it is String && pattern.matches(it) }
}