DOUBLE DUTY: Clothing for both Winter AND Vacation! I hate spending my hard-earned money on clothing that I’m only going to wear once on vacation. With that in mind, we are going to focus on items that you can wear in BOTH winter / spring AND on your upcoming vacation. travel / vacation / island / Key West / Mexico / island / Cancun / Cozumel/ Cabo San Lucas / Puerto Vallarta / Miami / Florida / Bahamas / beach / vacation / cruise ship / paradise / petite / over 40 / over 50 / over 60