diff --git a/vlib/cli/help.v b/vlib/cli/help.v
index 564f4a02ea..6255fdbc2a 100644
--- a/vlib/cli/help.v
+++ b/vlib/cli/help.v
@@ -4,9 +4,9 @@ import term
 import strings
 
 const (
-	c_base_indent = 2
-	c_abbrev_indent = 5
-	c_description_indent = 20
+	base_indent_len = 2
+	min_description_indent_len = 20
+	spacing = 2
 )
 
 fn help_flag() Flag {
@@ -39,15 +39,26 @@ fn help_func(help_cmd Command) {
 	if cmd.description != '' {
 		help += '${cmd.description}\n\n'
 	}
+
+	mut abbrev_len := 0
+	mut name_len := min_description_indent_len
+	for flag in cmd.flags {
+		abbrev_len = max(abbrev_len, flag.abbrev.len + spacing + 1) // + 1 for '-' in front
+		name_len = max(name_len, abbrev_len + flag.name.len + spacing + 2) // + 2 for '--' in front
+	}
+	for command in cmd.commands {
+		name_len = max(name_len, command.name.len + spacing)
+	}
+
 	if cmd.flags.len > 0 {
 		help += 'Flags:\n'
 		for flag in cmd.flags {
 			mut flag_name := ''
 			if flag.abbrev != '' {
-				abbrev_indent := ' '.repeat(max(c_abbrev_indent-(flag.abbrev.len+1), 1))
+				abbrev_indent := ' '.repeat(abbrev_len - flag.abbrev.len - 1) // - 1 for '-' in front
 				flag_name = '-${flag.abbrev}${abbrev_indent}--${flag.name}'
 			} else {
-				abbrev_indent := ' '.repeat(max(c_abbrev_indent-(flag.abbrev.len), 1))
+				abbrev_indent := ' '.repeat(abbrev_len)
 				flag_name = '${abbrev_indent}--${flag.name}'
 			}
 			mut required := ''
@@ -55,21 +66,21 @@ fn help_func(help_cmd Command) {
 				required = ' (required)'
 			}
 
-			base_indent := ' '.repeat(c_base_indent)
-			description_indent := ' '.repeat(max(c_description_indent-flag_name.len, 1))
+			base_indent := ' '.repeat(base_indent_len)
+			description_indent := ' '.repeat(name_len - flag_name.len)
 			help += '${base_indent}${flag_name}${description_indent}' +
-				pretty_description(flag.description + required) + '\n'
+				pretty_description(flag.description + required, base_indent_len + name_len) + '\n'
 		}
 		help += '\n'
 	}
 	if cmd.commands.len > 0 {
 		help += 'Commands:\n'
 		for command in cmd.commands {
-			base_indent := ' '.repeat(c_base_indent)
-			description_indent := ' '.repeat(max(c_description_indent-command.name.len, 1))
+			base_indent := ' '.repeat(base_indent_len)
+			description_indent := ' '.repeat(name_len - command.name.len)
 
 			help += '${base_indent}${command.name}${description_indent}' +
-				pretty_description(command.description) + '\n'
+				pretty_description(command.description, name_len) + '\n'
 		}
 		help += '\n'
 	}
@@ -79,14 +90,14 @@ fn help_func(help_cmd Command) {
 
 // pretty_description resizes description text depending on terminal width.
 // Essentially, smart wrap-around
-fn pretty_description(s string) string {
+fn pretty_description(s string, indent_len int) string {
 	width, _ := term.get_terminal_size()
 	// Don't prettify if the terminal is that small, it won't be pretty anyway.
-  if c_description_indent > width {
+  if indent_len > width {
 		return s
 	}
-	indent := ' '.repeat(c_description_indent + 2)
-	chars_per_line := width - c_description_indent
+	indent := ' '.repeat(indent_len)
+	chars_per_line := width - indent_len
 	// Give us enough room, better a little bigger than smaller
 	mut acc := strings.new_builder(((s.len / chars_per_line) + 1) * (width + 1))