Jennie says:

I hope one day you will address the plight of the taller woman.  I’m 5′10”, and I read your site a lot, and and I am mostly just plagued with jealousy about all the fabulous shoes you wear!  I really love the look of high heels and of course they do wonders for your legs and all that.  I have spent most of my years between sophomore year of high school and now wishing I were four inches shorter so I could wear high heels every day.

I know it’s easy to say I should just suck it up and wear’em, but when I do I usually spend the night (or day) feeling self-conscious and huge, towering over my more petite friends, and fending off comments from well-meaning people who say “Oh my God, you’re so TALL!”  It’s hard to feel attractive when you simultaneously feel decidedly un-dainty and rather giant-esque.  It’s just easier to wear flats.

That said, my boyfriend and I are going to a wedding in about a month and I’m going to wear a pretty form-fitting black dress–think pencil skirt with a built-in tank top.  I love the dress, but it just looks weird to wear it without heels.  Any suggestions for flat shoes that wouldn’t look totally bizarre with a dress like this one:

I’m of average height so I dont’ fully understand the plight of the tall woman, however I do know that when I see a statuesque lady in high heels I think she rocks. Just saying.

That being said, the last thing I want shoes to do is make you feel uncomfortable, so I’ll try and tackle your question the best I can.

To be completely honest, I don’t think you should wear flat shoes with the dress. A form-fitting pencil skirt is meant to me worn with a little lift, otherwise your legs — yes, even long ones — can look squat. And that’s the last thing you want!

My suggestion would be a kitten heel. While still a “heel”, it tricks the eye into a seeing a longer leg-line, all while keeping you pretty close to the ground.

These great red ones are only two inches and would give your little black dress great character. Plus, you can always pair them with dress pants or jeans later at the office. They also come in black if you’re going more traditional.

Jaeger by Chinese Laundry, $88.

Or if you’re looking for a strappy look, these would do the trick.

Prissy by Naturalizer, $64.

And who doesn’t love a little gold?

Akin by Naturalizer, $75.

I think it would be a good idea to check out the dress shoes selection from comfort lines like Naturalizer, Sofft and Aerosoles. These brands have really upped their style factor in recent years and are catering towards a younger demographic, while still keeping their signature comfort. Their lower heels may be just what you’re looking for.