I've taken MSP's advice to heart about wearing dresses more frequently. She's right; they are such an easy choice, at least in the summer when I can wear sandals. I am having trouble visualizing / planning work-appropriate dress and shoe looks for the fall and winter (I live in Canada, so sandals are out for the winter). I can only wear flats due to years of abusing my feet by wearing heels. I now have foot problems with the balls of both feet (Morton's Neuromas, in case anyone else has them), so heels are absolutely out according to my orthopedic surgeon. I can wear some flats instead of my granny orthopedics, if they are wide enough with supportive soles and don't have to wear my orthotics every day. What dress / shoe combos would be appropriate and what would be inappropriate? When does a dress and a flat just not look right? What kind of flats are OK and what aren't? I love the ease and professional, put-together look of dresses (and skirts). I just need to get the shoes right and this has stopped me wearing dresses and skirts for many years. I don't want to be held back any longer, and I am probably not alone in thinking this way. Advice please for all the gals like me.

I almost always wear flats with dresses/skirts. Just make sure that the shoe is relatively dainty and has a low-vamp. To get an idea of what I'm talking about, go to Zappos and do a search for "Esparaza Call it Spring" or "Anne Klein Bea" for the general idea. But, gosh, in Canada I'd probably only do shoes once in awhile because boots would make so much more sense. Tons of cute, flat boots out there that look fabulous with dresses/skits. Again, go to Zappos for some ideas: "Frye Paige Tall Riding" or "Frye Jillian Pull On" are nice. Of course, you could go for a shorter boot like mid-calf or even ankle-boots but I tend to avoid those with dresses for myself as I have short legs and they just make me look stocky. However, if you have long, slender legs, those styles might look quite fetching on you. Hope these ideas help a bit.

If the flats are beige or khaki, or dark and match your stockings, they are not even noticed. Red screams, look at me, I'm wearing flats. Flats can look dressier in patent leather, sequin, or with a tasteful ornament. I have seen some in fabric prints such as houndstooth and plaid that look really cool with coordinating clothes. For example, blackwatch plaid shoes with green wool skirt, white shirt, blackwatch plaid scarf. Personally, I like clogs, but they can have a European student vibe which may or may not be you. I like cordovan penny loafers, too, shiny and polished. Anything that looks like a tennis shoe , X. Wear a dress when shoe shopping!

Last year I started having terrible pain in the balls of my feet and couldn't wear any of my shoes. I went on Amazon.com and searched for the shoes with the greatest customer satisfaction and read reviews and ended up buying these shoes made by crocs. I know Leslie doesn't care for crocs, but I'm telling you, they healed my feet! I have 5 children and they say they look cute on me with dresses or with pants, and 2 of them are teenagers. The sandals in the picture are comfortable, but not like the ballet slippers. I have the ballet slippers in many colors, all of my neutrals and couple of fun colors. They are made of rubber. I wear a size 10 shoe for most sandals, but always a size 11 shoe for sneakers and boots. In these shoes, I wear a size 10. If they feel a bit tight when I buy them, they soon conform to my feet and stretch (especially if I wore them with socks around the house for a bit). I looked silly with them in socks, but I wore them all winter too because they were the only thing I could wear without pain. After a year of wearing them, I am able to wear my other cute shoes for special outings, but not for every day. Hope that helps.

MSP rules---as I understand them 1. Wear shoes without an ankle strap to give the look of longer unbroken leg line. 2. Short ladies will look shorter with very long dresses. 3. Those wearing orthotics should wear pants or longer dresses. My situation---after wearing orthotics better than 30 years 1. I am still only 5 feet tall. 2. I still need to wear orthotics. 3. I still cannot wear orthotics with any shoe but lace-ups or an ankle strap.

It would be nice if MSP's recommendations would consider that many, perhaps most, of her subscribers are unable to wear high heels or unsupportive flat shoes. Many of us find it downright painful to wear heels at all. As we get older, the muscle and fat pads on the bottoms of our feet get thinner, and we need more sole cushioning than styles designed for 20-year-olds can provide. I realize that MSP's goals include recommending fashionable things, but most of the shoe styles she recommends would hurt my feet. Moving right along in a more postive direction, there are a few brands that have room for orthotics in some shoe styles. SAS is one. Soft Spots and Naturalizer shoes I have seen also have more padding and some have more room. As I think MSP pointed out a while back, matching the shoe color to your leg color makes the shoes less visible (and more versatile). Adding ankle straps can make the shoe a lot more stable. Accents such as jewelry, handbags or jackets are a better choice to add fashionable flair than high heeled or unpadded flats that hurt.

I'm only 34, but I have also had trouble with lots of foot pain due to my high arches. I agree with MSP that we petite ladies need at least a slight heel to look our best. My solution has been to shop carefully for wedges that aren't too chunky. Since I'm a SAHM-SYSter, I can choose my timing on shoes. For example, knowing I'm only good for two to three hours in dress shoes, I'll wear them only during church then slip on a pair of comfortable but sassy slippers or sandles I brought with me in my tote afterward. I live at the end of a long dirt lane, so it's usual for me to wear mud boots and change them out when I get to town. Maybe some ladies could adapt this idea and keep a pair of orthotics in their purse or desk drawer.

Thanks for posting this! I am pretty resistant to the idea of wearing heels because I find them uncomfortable and I don't want to end up with serious feet problems like the ones the OP suffers from! :( It's great to see commiseration and suggestions from others. My solution, like baryj1, is to look for low wedges that are more wear-able for me as a teacher and active young person than high heels. I'm currently on the hunt for some beige or nude low heels to incorporate into my wardrobe to go with dresses and skirts. I love Naturalizer and St. John's Bay for comfy work shoes.