Worth it or not (no. 4)

Both of these pairs of shoes cost right around $70.00. Both are from Macy's. However, one is suitable for wear by a beach bum who sleeps under the rundown boardwalk on a nondescript New Jersey beach, while the other is suitable for wear by a cute master's student on a second date. Which is which? More importantly, which kind of person would you rather be?
If you thought the top one, by Timberland, was more appropriate for people with an actual abode, complete with doors and a mailbox, good job, you've passed the test. If, however, you thought the bottom pair, by Ben Sherman, was suitable footwear for someone with more than one pair of pants, you need to reread your "Style for Dummies" handbook.