For the past few years I have taken two trips to New York in the spring—one in April, to see my best friend Susie, who lives in Rye, and the other in June, when Bruce and I have been guests of our friends Dan and Cynthia at a fund raising gala hosted by their son Jacob Lief for his organization, The Ubuntu Education Fund.

The weekend in Rye usually involves a train trip into New York City to see a show, go to museum, or go shopping and have a meal. I love these trips because they are the times in which some of my best memories are made. To experience the cultural differences between a tiny Maine island with a winter population of 70 and the most populous city in the U.S. is a real shot in the arm after a long cold winter. 

However, getting ready to go involves packing. Trying to figure out what to take to wear in New York City is one of life’s more stressful activities for me. In fact, it ranks right up there with writing this column and moderating a town meeting. All three involve putting myself “out there” in a way that makes me extremely uncomfortable, even though I know I am capable, and afterwards I’m very glad I made the effort. 

I am my own worst enemy when it comes to judging my “city” wardrobe. For some dumb reason I don’t want to look like a tourist in New York and I know my clothes could give me away. Call it ego, vanity, comfort level, whatever; I’m just usually a little disappointed in what I’ve chosen to wear.

Maybe I am scarred by the first time Bruce and I went to New York to visit Susie when she and her then husband lived in Manhattan. It was 33 years ago, and while I don’t remember the travel details, I remember well showing up on a Friday afternoon at Susie’s office in New York where she worked for Cuisine magazine. I had on a mauve chamois cloth wraparound skirt, some knee high brown lace-up leather boots from college days, and a cream-colored turtleneck sweater. I felt comfortable in my skin and excited to be in the big city with my handsome husband.

I was confident that I was well dressed for New York. When we arrived, the receptionist at the front desk pressed her intercom and said, “Susie, there are some L.L. Bean types here to see you.”

Some of my packing paranoia at this time of year comes from the fact that New York is usually a good four weeks ahead of us in warm spring weather. On TV, the local weatherman is lamenting the fact that we haven’t seen 70 degrees since Oct. 11. On the island, I’m still comfortable in sweaters and socks while my city sisters have already pulled out their sandals, their lightweight summer clothing and chic little jackets.

I’m out of practice for putting together a breezy spring look. It could still be cool, so I will have to pack layers of clothing. Then there is the shoe issue. In the city, we do a lot of walking on hard sidewalks for miles and miles. I love it all; the sights, the sounds, the energy, but my 61-year-old feet and knees do not. I wear good arch support in my shoes to avoid plantar fasciitis, but I feel like a clod in my sneakers, especially if I want to wear a skirt because it’s suddenly 80 degrees. 

In June we will only be in New York for two days, and yet I will be packing chunky walking sandals in case it’s hot, sneakers in case I get over myself, loafers (with Birkenstock arch supports) to wear on the plane and a pair of fun dressy city heels for the gala. How will I fit everything in a carry on bag along with those layers of clothes? Somehow, I always seem to manage.

Recently, I had a delightful weekend visit from my brother and a good friend of his who had never been to New England. Lynn lives in Washington D.C. and does a lot of traveling for work to places like London, Rome, New York and Palm Beach. I’m not sure if she worried about packing for a weekend on a tiny Maine island, but I do know that before the trip, my brother sent her an e-mail with several links to articles of clothing on the L.L. Bean website, and the fashion/packing advice to “Think camping.”

I promised myself that when I turned 60 I would stop worrying about this kind of stuff. Apparently I’m still working on that, but I also know that for 360 days of the year, I’m actually quite comfortable being “an L.L. Bean type.” 

Barbara Fernald lives, writes and wears it well on Little Cranberry Island (Islesford).