Red striped tee, Boston hat, white boat shoes

This denim jacket outfit (bottom pic) did not look nearly as cute in reality as it did in my head. That could be my denim-jacket anxiety talking though. Ever since I owned one in many years ago I've had a serious aversion to them. I thought a little exposure therapy might work, like if I brought one home perhaps I could coax myself into loving them? They look so cute on other people! I'm not convinced I feel comfy wearing one, so in the meantime I put together an outfit (top pic) with this same red stripe top that I like much better! (Note: this top is a tunic length, I've got the end folded under in both photos.)

Jacket: J.Crew Factory
Top: J.Crew Factory
White jeans: Gap, $30 (similar)
Blue jeans:H&M, $32 (similar, similar)
Shoes: Minnetonka c/o DNA Footwear, $53 (similar)
Purse: Calvin Klein/Macy's, $130 (similar, similar)
Hat: Boston street vendor (similar)
Approx. dates: Hat is 8 years ago. White jeans are 5 years ago. Blue jeans and purse are 2 years ago. Shoes are last summer. Top is new.