Comfortable Fashion Boots -- an Oxymoron?

Since everyone's feet are different, the only way to really know what will work best for your feet is to try on a lot of different brands and styles and get to wearing them a lot now so they are well broken in before your April trip. For flat or low heeled boots, I've had good luck with Merrell (which does make a number of styles that are dressier for city wear as opposed to their line of hiking boots), Aerosoles and Clarks. No idea if any of these stocks their dress boots for large calves, but I know they have some styles available in both M and W widths for the footbed. Since I live in a city where there are lots of cobblestones and brick sidewalks, I try to avoid walking around much in narrow heels (stiletto or kitten heels) since those are easily caught up in uneven sidewalks and streets. A wedge heel or a thicker heel base generally makes it easier to walk across cobblestones so you'll avoid scraping up the leather or breaking a heel if you catch it between the cobblestones. I've brought dressier boots on Fall and Winter trips to visit family in Europe, but I always bring a pair of flats with me so I can alternate as it helps me reduce any possible problems with my feet if I can swap out my shoes and it's always good to have a backup pair of shoes in case 1 pair gets soaked in the rain and needs to dry out.

First, if you're only bringing one pair of boots, wear them on the plane...it's way easier than cramming them into a suitcase! If you must pack them, put them on the bottom as flat as possible. Not easy, but it can be done. I swear by the flat Frye boots. They are NOT CHEAP. But they are very comfortable. Also, the footbed tends to be roomy, which is good for people like me with slightly wide feet, and there is plenty of room to put an insole in there. I wear them around the city for work all day all the time without insoles or issues. I'm planning to bring them to London/Paris this November, possibly with an insole in there, to wear all day long. I've convinced my mom (60) to buy a pair for the trip as well. If I'm being honest though, I have a bit of a shoe/boot obsession, and I will actually be bringing more than one pair. :)
Most Frye boots have extended calf sizes available. They also come in a variety of heel heights, shaft heights, and colors. My suggestion would be to shop on Zappos.com. They have wonderful customer service and free shipping both ways, should you want to return them. Also, they have a 365 day return policy so you can wear them around your house for as long as you want to make your decision (just don't wear them outside). Additionally, I find their comment/review sections really helpful. Know this though: generally, the reviews say to size a half size down. Because my feet are a hair on the wide side, I stick to my normal size. I tried to size down, and it was too small.

I have been very happy with my Merrell boots. I bought some waterproof ones that I could wear out in the snow. They were fashionable enough to wear with dresses or pants. The boots, along with a pair of dress shoes, were all I needed footwear wise when I went back home at Christmas.

I swear by Keens. Have four different pairs. Lots of miles tread, hiked, strolled, climbed, in each pair. Nary a blister. Pricey but in MHO worth every penny. Check out the styles. www.keenfootwear.com Traveled with the Presdios,
Alamosas, Prescott Mary Janes. Always travel with two pair and alternate. Check the website and see if something appeals to you.

Love my Frye boots.

I love my Frye boots, but I cannot wear them for more than a few hours at a time. They are a bit tight for my foot and I don't know that I would be able to walk for hours in them. They also have quite a stiff sole. I have some super comfortable Born cowboy boots that look good. Every pair of Keens I've had have been a joy to be in. I have a pair of snow boots from them that are warm and comfy, a pair of great hiking shoes and a pair of sandals. I have recently been wearing the sandals and walking about 15 miles per day, and while I am tired, my feet don't hurt like they do in other shoes (like Teva or Nike). Keen makes a wide variety of shoes including some good city boots. I'd recommend those. I do also have a pair of Merrel running shoes that may be my favorite shoes I have ever owned, but I cannot speak to their boots.

Try Lowa (hiking boot) or Frye boots which look fantastic and are very comfy! Ecco makes boots as well. Good luck

I have a 10or 12 year old pair of Wolky's low boots, flat soles, which are every bit as wonderful as the day I bought them. They go on every winter Euro trip and keep my feet warm. Wolky soles are lightweight & handle cobblestones very well. Waterproofed, low boots are IMHO easier to travel with instead of full boots. There are convenient ecco and wolky stores in Amsterdam, btw.
Also fyi, I've used silicone spray from a camping store to waterproof my already broken in maryjanes for non snow day winter travel- as long as it isn't suede or nubuck, just an idea.

Lo, you might also consider Clark's. I just bought the Clark's Charlie boot (comes in 3 colors - black, brown, grey). Since the Clark's website does not offer coupons or sales I bought them from a different site.
http://www.zappos.com/indigo-by-clarks-charlie-zip-british-tan-leather

Thanks to everyone who made suggestions. I followed through on all of them, but getting anything to fit my 18" calves was a no-go. As much as I love Frye boots, their suggestion was to have the 16" circumference ones stretched. I ended up with Lumiani Laila Extra Wide Calf boots that I got through Zappos. I was able to get size 10W. The circumference is 19" which gives me a little room at the top so I don't have muffin calves. They fit perfectly, and even though there is no zipper, I can get my high arched thick foot into them with padded compression socks on and orthotics in the footbed. Go to the link if you want to see them. I got red ones. Thanks again everyone for your help.

Those are really cute. I would be interested in knowing if they are comfortable after walking for a long time. Do they only come wide with a wide calf?

I too will be interested in seeing how they feel after being on my feet in them for a long time. That's why I was thrilled that I could wear them with both padded socks and orthotics. They come in medium and wide widths and in a wide calf that is 17".

I don't need the wide/wide, so that's why I was asking. I'm always interested in comfortable shoes!

I realize you are not going until next spring, but would love to know how they do, especially on cobbles!