Going off island requires a certain reconfiguration of mindset. The wearing of a pink tutu just won’t do.
There will be hoards of commuters and lines of cabs and lots of noise and smelly buses and anxious, irritable people with phones for ears and anxiety where smiles should be. There will be pavement and potholes and skyscrapers and sprawling suburban cookie cutters.

Not that we don’t have all those things in Key West. We do; well, except for skyscrapers and cookie cutter houses. Key West is pretty much Manhattan without the high rises. Here on the island, though, it’s hard to internalize angst while wearing a swimsuit cover-up for Saturday errands.

Few go “off island” willingly, not even to Stock Island, or, heaven forbid, Marathon. It requires too much reconfiguration. Not to mention a digging into the back of the closet for what are now slightly mildew-y and excessively out-of-date mainland clothes and hard shoes. (Although to be fair, a trip up the Keys, as long as one does not end up on the Florida mainland, usually allows for Key West casual.)

A few turns of the annual calendar are enough for the brain to assume Key West is the real world. That flip flops with a sparkly button constitute dress shoes. That a pair of linen pants and a sequined T-shirt are cocktail attire. That long pants, which aren’t jeans, are business appropriate.

Going off island begs a question about smarts, especially in the winter. It’s minus-freezing degrees anywhere off island and the coat, hat and gloves you once had are in a storage unit somewhere under the old Christmas decorations. The only boots you have are the red Wellies used to ford flooded curbs, and they are neither style- nor warmth-appropriate for the District of Columbia or wherever real people congregate these days.

Back in the olden days, which roughly translate into any time before 2012, a trip to DC was as unremarkable. Navigating of O’Hare? Piece of the proverbial cake. Packing for a week of corporate meetings? I had lots of matching power clothes and could make them fit in a carry on.

No more. Two weeks after I walked out of the News Tower in Rockford, IL, for the final time over two decades, I boxed up corporate suits, shoes, coats and accessories and donated them to the woman’s club. If I wouldn’t or couldn’t wear it in Key West, I paid it forward for someone else.

That was, of course, marvelous therapy for the next life. Today, six years later, anything that did make it to the island is hopelessly dated and a bit sniffy. Packing for a business meeting these days requires re-wearing of a red leather jacket and a black Hillary Clinton-esque pants suit that hang in the back of the closet awaiting their twice or thrice yearly trek to big cities.

As I searched for hard shoes and a pair of pantyhose for a recent off-island adventure, it occurred to me that perhaps I could splurge on a retail shopping experience. Replenish the off-island wardrobe and some cute shoes. Nah.

Linda Grist Cunningham is editor and proprietor of KeyWestWatch Media, a digital media management company that publishes Key West Island News. She will admit to having squirreled away a 40-year-old mink coat just in case.