So, I love cons and skirts. However, I think they look best though with knee length or above. Shorter knee length with wider skirts, and longer knee length with skinnier skirts. I think the key is to play girly off of tomboy.

Even if you do find a good cons/skirt match, I don't think cons are the answer for your travels though. My old, very well loved low top cons still give me blisters if I wear them without socks on a hot day and do a lot of walking. If I wear them with socks, the only ones that don't slip down and drive me nuts are the ankle high ones. None of the low cut ones that won't show ever stay up for me, not even the ones that converse makes specifically for wearing with low tops. To me ankle socks and skirts are a no go look, so that's where I come out in the cons and skirt debate. I wear them, but only when I'm not walking around all day.

Thanks so much for chiming in, kcanshop! Great to hear about it from this perspective.

Would you consider something like this?

http://vip.zappos.com/product/7933983/color/202581

It would be a bit "Coals to Newcastle" since Pikolinos are made in Spain, but I've had great luck with Pikolinos. They wear beautifully and are super comfortable and well made. I love a flat plus mary jane styling with a closed toe. They have many more styles, if these don't suit you.

I'm with you in not liking the athletic shoe + mary jane from Merril and others. They just don't delight me, even though I know lots of other folks love them and they look nice enough on them. You aren't alone. There just aren't many of us.

Oh, these are really beautiful! I could definitely see myself wearing them. But Pikolinos are also rather narrow, at least the ones I've tried so far. They aren't available much here, but I've tried one a few in one store I was in some time ago and they all were too tight.

Do you have to have a wide width, or can you do a regular width that is wider? (I ask because I'm the latter.)

Brands for comfort and walking that I like:

Aersole
Camper

I'll put in a plug for my mother's favorite, New Balance. Yes, they make sneakers. But they also have two lines of dress shoes, Aragon and Cobb Hill. This is the only brand my mother will wear. She has super fussy feet -- albeit narrow. I have never tried these but I know NB sneakers work for wider feet like mine, so it may be worth a try.

You mentioned oxfords. Do you like those because they have laces? My mom insists she needs laces too, for the support. A pair of flat oxfords could look quite cute with a skirt, of any length. I have a pair that I swap into when I'm walking to get somewhere, swap into heels once I arrive. I've worn them with formal dresses. I see a lot of people here in the city wearing flat oxfords with skirts and dresses.

Oh, I do really like those Pikolinos. This has been an interesting thread. When I first saw the title my honest response was, I have done this but only due to being pregnant. I do agree though that a shorter hemline can work well if styled well. Would you not consider some flat ankle boots at all? They could be sturdy. It seems like there are a lot of nice menswear-inspired oxfords (aka not too flimsy) in stores. I have really been liking the look of those and they could work with skirts. I do like the look of those boots you showed in 3, but I don't think they would work with a skirt unless you are extremely young and punky.

Astrid, I share your sadness over too narrow shoes! I promise you as a fellow wide footed girl, the Pikolinos can work. The leather is very soft and I wear them as do my sister and my mother. You could actually call my mom a duck, she's got a double wide foot! But so sad that they won't work because you can't get them there. The Pikolinos site does ship to lots of places, if that helps! They have a DE/"I am in Germany" option on their site!

I wore something like these all over England and France one summer, even with my wide foot: http://www.pikolinos.com/de/en.....-8995.html

Oooh and look at how cute these are in red (which is usually a brownish red in Pikolinos!). http://www.pikolinos.com/de/en.....8312L.html

That website is addictive!

Shiny, I can do normal shoes if they are wider. It always depends on the shoe, I normally try on everything! I don't have Camper shoes, but I've tried them before in the stores and they can work. I do like oxfords because of the laces and I like the dressier and more classic look in comparison with sneakers. I agree that oxfords are great with skirts and dresses and I'd like another pair that are more robust (men's inspired) than the ones I have. I just thought that this weren't the best shoes to take on a trip like this. I'm going to have another look this week and see if I find a pair that's robust enough.

Scarlet, what exactly do you mean when you say flat ankle boots? I'd consider some oxfords if I find ones that are sturdy enough. I agree that the boots in #3 might not work with a skirt, but if they replace my hiking boots and bad weather shoes to wear with jeans that's not a problem.

kcanshop, good to hear that they might work. I don't think I'll order there now, but I'll keep it in mind and maybe try them again some time when I have more time to order and return. I especially like their summer shoes, I think I might try them for sandals next spring.

Cons come in wide, Astrid! Add an insole for extra cushioning, or even an orthotic for arch support.

I love youngsters like you in Cons with skirts sans socks. So cute!

Oh, sorry, what I really meant was flat booties. Like these for example
http://www.bottines.nl/products

Also with shoes like Cons I like to wear those little sockie things from Falke that don't show.

Makes sense about the shoes in 3 especially since the vibe of that shoe has clearly been singing to you for awhile

Thanks Angie! I hadn't even thought about adding insoles to the Cons, but that might be worth a try.

Scarlet, I think so too. I actually bought one of these Falke socks after you recommended them some time ago to wear with my oxfords. They work reasonably well, although I always have problems with the socks sliding down when I wear these low invisible socks.