I go through it every single year, hence the “annual” shoe dilemma. Every. Single. Year. Allan once observed that I am the type of girl who needs concrete under her high heels. Tthat pretty much sums it up in a nutshell. I am fairly small in stature – about 5’ 2” (5’ 3” if is stand up very straight and lift my chin), but I prefer to appear taller. Therefore, ever since the age of about 13, I’ve worn high heels. In fact, there was a time during my life when I did not OWN anything other than very, very high heels. At one count a few years ago, over 130 pairs! Have you ever tried walking on the beach in 4 inch stilettos?? I have.Trust me, it can be done. As I’ve gotten older, I’ve discovered flip flops and some shorter heels, but I still feel most comfortable, and most attractive, in very high heels. This is usually not a problem. I work in a law office and most of the time, heels are fine with my skirts, my jeans, or whatever. When the dilemma presents itself is on our annual trips to the United Kingdom -a place filled with cobblestoned streets and where we tend to walk about 10 miles a day. High heels just don’t cut it on our trips. EVERY year, I start looking about six months prior to our trip for something to put on my feet that is: (1) comfortable; (2) attractive; and (3) keeps my jeans from dragging on the ground and getting mucked up. You’d think that with 11 trips to the UK under my belt, I’d have solved this problem by now. Think again. I have spent the past six months on an unsuccessful quest to buy a pair of shoes that is both comfortable and attractive. Every year I think I’m going to get it right and every year I fail. Here are a few of my “misses” over the years, and a couple of “almosts”. I have absolutely NEVER felt entirely comfortable in a pair of shoes I’ve worn on one of our trips. I usually end up reverting at some point to an old pair of sneakers that I use at the gym, having tossed them into my suitcase for just such an emergency, and then feeling incredibly awkward. Wearing that type of shoe for an entire day is so alien to me that I almost feel like I’m not in my own body.

The Annual Shoe Dilemma

This is my typical shoe. It makes me feel good and it makes me feel a bit taller. But for obvious reasons, it just would not work on one of our trips.

Back in the late ‘80’s I had some flat-soled boots that were not too bad. Worn on trips in 1989 and 1990 when leggings with long sweaters were very much in style. I don’t think I even packed a pair of jeans on those two trips, so didn’t have the dragging hems problem while wearing totally flat soles. But no arch support whatsoever. Alas, those boots are long gone so I can’t show them to you here.

This is a pair shoes I tried one year with a small heel. I think I wore them just one day and my feet hurt so badly I tossed them back into the suitcase to be replaced with the old and ugly pair of gym sneakers. I don't think I've ever worn them since. Don't really know why I still have them.
These lace-up half boots were purchased for a trip in October of 1998 when I thought we’d have a lot of rain. They were not too bad, except I’d not broken them in properly before the trip and they chafed terribly against my ankles. Tossed back into the suitcase and replaced by the horrid sneakers.

I’ve worn these medium heeled boots on a few trips. They are fine in the mornings, but by afternoons having walked on lots of cobbles and climbed many stone castle stairs, my legs and feet begin to ache. Once on a trip in 2003 while wearing these I had to sit down in Covent Garden to rest my feet and was convinced by Holly to go into one of the expensive shops there and purchase a new pair of very pricey and very ugly sneakers. Here they are. Aren’t they just hideous? I ruined a pair of equally expensive Max Studio black velvet jeans by wearing them with these sneakers over the next few days with the hems dragging across the dirty cobbled streets. Just totally shredded the hems.

In 2004, I actually took two pairs of shoes that were the most comfortable I've worn on any trip so far. It was September, and both pairs were open-toed shoes. I probably could not have gotten away with this type of shoe on an October or November trip. These shoes were slide wedgies and did the job of keeping my hems from dragging. The only problem was stepping off the train every day at Hampton Court Station. It’s a pretty big step down at that Station and I was always afraid of losing my shoe entirely or twisting my ankle.

Even though on the 2004 trip I was pretty happy with the shoe situation, I still ended up having to purchase another pair of VERY EXPENSIVE shoes in Salisbury. We were taken on a very special private tour at Hampton Court where a bit of major climbing was required so I needed a good-gripping shoe and the wedgies just didn’t fit the bill. I think I paid the US equivalent of about $120 for these little slip-ons and had to roll up my jeans in a very unattractive fashion while wearing them that day. This was one trip that I’d not brought the old emergency sneakers. I think I’ve worn these little slip-ons only once since returning home from that trip. Oh well.

We are getting ready for our 2005 trip. I began my shoe quest in January or February. I researched various styles on the internet with the help of Holly. After several days of deliberation I went to Nordstrom and bought these. I figured: wedge type heel (good for keeping pant hem up off the ground). Mary-Jane style (won’t slip off getting off of trains). I was hesitant about the suede (it does tend to rain in England and suede discolors when wet). But I thought I’d give them a try. Well, I wore them on a two mile evening walk with Allan a few weeks ago and spent the next week nursing robin’s egg sized blisters on both heels. I’m afraid these cute brown Mary Janes are going to remain in my closet for a long time, or be sent with the next batch of stuff I take to Goodwill. (Update: Shoes returned to Nordstrom, without receipt, four months after purchase and before trying them out in England. Explained the blister problem and they took them back without question. Great customer service at Nordstrom. They've got a customer for life!

I’ve decided to take both the open-toed wedgie slides this year in spite of our trip being in November and also the medium heeled boots. Perhaps I can alternate them. I will also toss into the suitcase the ugly pair of old gym sneakers just in case I get desperate. Holly cannot believe that I am actually going to attempt to wear open toed shoes in England and Wales in November. She says that when I get frostbite on my toes, she’s putting me into an expensive black cab and sending me off to have my toes removed while she continues to go about enjoying her time in London.

Well, we are now back from the 2005 trip and I wore these shoes 9 out of the 10 days we were in the UK. Not particularly nice looking shoes, but my toes were happy and free and the hems of my jeans survived intact. I managed to avoid frostbite even though it was pretty darn cold in Wales. These are keepers. Now back to my high heels.