This bit of backstory was written in May 2016.
I like to think of myself as a practical, earthy woman. Upon preparing to downsize from the Edwardian flat in which I lived for 13 years, which had a closet in every room, toward the sailboat which would become our eventual home, I was shocked to discover that I owned 45 pairs of shoes.
I’m off my foot right now due to an injury, and I found a bit of fun in reading these descriptions. I think I might go sit on the floor and consider my shoes now… many of them are jumbled together in a bag. Shoes that I got to serve me in a job I hated, shoes that served me before I turned 40 and could somehow effortlessly wear high heels without excruciating discomfort (who was that girl?), shoes that love me back. There is a red pair of Danskos that were in storage for months while we were traveling and moving, and which I obviously can’t wear at the moment. They are the first pair I will reach for once I can walk normally again! Yes, I’m going to go look at them now.
So, Kristie. Which pair(s) made the cut for life onboard?
Which pair do you think you will reach for first when you tap into storage items in the future?
Jennifer, my compassion to you on your injury. I’ve had a broken toe for the last few months myself, and I feel you! I broke it, healed it, gleefully ran two times… and then stubbed and rebroke it. I wish you speedy healing and into your red Danskos soon!
I love your questions! Let’s see. I have one locker for shoes, because I like to have happy feet, and I really like shoes. It contains:
#3, the Ugg boots, which were essential to my comfort and happiness while living on the water through the Bay Area winter! They were supplemented by a new pair of Ugg slipper-moccasins at Christmas, because I’d let go of all my other slippers and wool was the key to winter comfort.
#13 my hiking boots.
#21 my sailing Keens. And for my birthday boots this year (my birthday is in December and many years boots are what we buy me) I got a pair of Dubarry sailing boots. The #9 Helly Hansen boots were not warm enough and left during The Great Gifting 
#26 my wool Birkenstocks finally ripped to shreds on the year between writing this in SF and moving aboard. I replaced them with a new pair: white wool, white soles. The wool is imprinted with a snakey texture and the white wool is spattered with gold. They are absurd. I adore them. They are getting pretty filthy. I am embracing the concept of “Star Wars White”, which James introduced me to. It’s a white that says you’ve been kicking some ass!
#27 the Betsey Johnson stilettos went into storage and then came out, which answers your question about which pair I will reach for first when I tap into storage! We went back for those shoes, my best silk nightgown, and my favorite sheepskin-trimmed shawl one day when I realized this is our whole life now, and I do not wish to only be practical, and dressing up the girl sometimes makes us both happy.
#28 the running sneakers got replaced with a pair of Merell Vapor Glove barefoot running shoes. My feet are so much healthier in them and my gait is great! I’ve had them over a year and bought a second pair, too.
#33 the black leather flip-flops.
#38 nice leather sandals. These have since weathered a magnificent and astonishingly rainy afternoon in New Orleans; we’ll see if they recover to wearable status. They might be leaving soon.
#31, the brown Mary Jane Crocs. And another pair, Croc clogs, which weren’t on this list because they were already on our first boat. I realized that the clogs, which I’d bought for traveling in India in 2010, were 8 years old and the bottom was entirely slick, so I tossed them and replaced them with a white pair.
2 pairs of Chacos. One grey with doubled grey ribbons, one white with a single white ribbon. Yes, I currently own three pairs of white orthopedic shoes: Birks, Crocs, and Chacos. It’s a fashion phase I’m having. It cracks me up.
So that’s 15. And there is one more pair of dress shoes that I don’t see on the 45 pairs piece but are old and more walkable than a stiletto; they are my main dress-up shoe. Which makes 16 pairs of shoes I’ve got onboard. Oh wait I just bought a pair of gold Havianas for showering at the marina. 17!
A few of the 45 are in storage, but most of them left, as I am pretty sure I’m not going to be willing to have uncomfortable feet nearly so much in the second half of my life as I was in the first.