Let's be clear, I am a flats girl always and forever...but, I do recognize that heels are sexier in general and especially to guys. So, when it comes to a first date, I am always torn; I think flats say "hi, i am not trying too hard, but still look effortlessly stylish" while heels say "hi, i could potentially be seriously high maintenance but my legs look great." thoughts, opinons, ideas? Guys-can you weigh in here?

Hi Anne:

The omly way that a man would think you are high maintenance is if you are! Flats are fine for a first date if you are going to play miniature golf or go hiking but if your first date is courting you to dinner, then you must submit to the heel.. it doesn't have to be Christian Louboutin's platform 5 inches plus but it should say subliminally, i am making an effort, I care about myself and i care about meeting you.
Barbra Horowitz
Author Closet Control
Host-fashion 411-karmasolradio.com
www.barbrahorowitz.com

The most important thing on a first day is simply feeling beautiful and being at ease with oneself. In the shoe department therefor they have to be comfortable! There’s a way to wear heels (not crazy 6 inch Louboutins) and feel sexy without the kind of visual effort that might read, as you worry, ‘high maintenance’. Again, I think any woman who is wearing a reasonable heel and can walk seemingly effortlessly will not read as fussy. If the heel thing still doesn’t work for you, I’ve always found a classic wedge to be a great middle ground! (Side note: I’m also shocked by how equally uncomfortable many flats can be these days!)

Hi Anne,
Unless you're going on a really casual daytime date, I would always wear heels on a date. If you're worried about looking too high maintenance or like you tried too hard, temper the heels with a pair of jeans and a chic top that's not overly revealing. Most guys love a girl in heels even if they won't admit it. If you live in NYC, just make sure you wear heels that have been broken in well enough for you to walk several blocks in them. I think what really makes a girl seem high maintenance in the city is telling your date you have to take a cab 3 blocks from you dinner destination to your drinks spot because your feet hurt!
Beth
Owner of Il Primo Passo -for shoe addicts-
www.ilprimopasso.com

You know, I think whatever you feel most comfortable and yourself in would be the right answer. On that first date, focus more on letting your best personal qualities come through before you start to worry about elevating your look. If the fact that you were or weren't wearing heels is enough to be a deal breaker on the first date, the guy's got issues and you probably don't want to go there.

And speaking just on my own personal preferences, flats rock!

Hi Anne - I always go for high heels because if it's "serious" you need to see how he feels if you're towering over him!

I think comfort is the best rule of thumb. There are already so many other things to worry about on first dates, the last thing you want to worry about is sore feet!

The one thing I always say is that most men do not even notice your shoes unless they're gay........but they do notice your legs on up ..........so, if your legs look great in flats (ie your 6 ft tall and weigh 105,) enjoy your flats, but otherwise, go for the heel.

Anyone who cautions whatever you feel comfortable in, is probably not getting much action.

PS. if we do comment on your shoes, it's because we want to tell you how great your legs look, but know that we're not allowed to say that on a first date. We've had training too!

Hi,

I suppose you really could do well with either both! I think as a cardinal rule, however, that people should only wear heels they can comfortably walk in. I feel so badly for my friends when they squeeze their feet into a pair of (admittedly dazzling) heels, but have to walk like they have weights at the bottom of their feet. If this isn't a problem for you, then you're one of the fortunate ones! But I'd say that a first date can be nerve racking enough for many. Better to be as comfortable (and stable) as you can!

As you are a flats-forever-and-always girl and they are most fitting to your personal style, wear them on the first date. Then amp it up on the second with a pair of killer heels and knock him dead!

Normally, I would suggest heels for that obvious sex appeal, but since you mentioned you're really a flats girl, I would compromise with a kitten heel, and some seriously sexy underwear! He may not know about the underwear unless you choose to display it, but it will give you the sexy you-wish-you knew-what-I-was-wearing-beneath-this confidence.

I think wearing a peek-a-boo open toe high heel is perfect for a first date especially with a bright pink or red nail polish, and if you are really head over heels for the guy, meaning he is really your type, fine, athletic body, and its not a blind date, You really want to impress! I know it can be a lot of trouble but it will be a lot of fun and you will thank yourself in the end when he tells you how unforgettable that night was or how sexy you look, because first impressions really do matter. He'll forever think of you as his classy girl he has to impress or take care of, not necessarily high maintenace, men don't equate price with dressing sexy, they see it as a total girl thing ,unless you are telling him how much they cost or where you got them from. Men don't know that kind of stuff. So just have fun ,then on the next date you can wear flats from then on, its just the image of I'm a great catch you want to leave in his mind.

firstly, i think it depends on the height of your potential man. tall ladies i know its harsh but you should generally avoid heels like they are the plague. guys hate to feel inferior and height on your behalf will do that.
otherwise, heels all the way. height does not matter unless they make you look like a hooker. also, note that wedges are for women who have not learnt the art of walking in heels. also avoid. '

hope this helps

Okay, I am going to weigh back in here again and disagree with estylist (sorry!). I've been giving the question on whether a girl should wear heals when the guy could potentially be shorter than you a lot of thought lately.
For instance, when Nicole Kidman first started dating Tom Cruise, she wore flats, but still towered over him. She wore flats for long time and then suddenly as her image grew, she started wearing the stilettos!

I asked an old boyfriend of mine to weigh in last night and speak for men. He was 3" shorter than me in our barefeet, and I asked him if guys really have a problem with taller girlfriends and the height of the heels they wear, or is it something women feel? He answered that many women want a man who is taller than them. Men, for the most part don't care because they are looking for other qualities both physical and character wise. He said some men have the chip on the shoulder over this because they may have been passed over by potential dates because of their height, and those guys clearly have let this become an issue for them.

So, I believe that now women should wear whatever shoe makes them comfortable with a potential man. If they want a man who is seemingly taller than them, wear the appropriate height shoe. If you don't care what height your man is compared to your height, still wear whatever shoe you feel most stylish, and sexy in! Its all about confidence, and giving a potentially great guy equal footing (sorry!) to meet a wonderful person, namely you!

My first question would be...can you walk in heals? If not...or if it ends up giving you a strange walk than you're better off wearing a nice pair of flats...maybe pick really feminine ballet flats and instead of completing your outfit with shoes start from the shoes and go from there… now if you’re just as comfortable walking in heals as in flats consider your friend’s height and find a somewhat comfortable heal but only if it improves the way you feel about yourself and increases your seduction potential!

Now I have to weigh in! I think the most attractive thing to wear on your first date is confidence. Whichever makes you feel most confident wear those!

And about the comment about tall women wearing heels, complete rubbish! At 6'1, I live in heels, and wouldn't have it any other way. If the man I am dating has issue with it, then he's not the man for me. Again it all comes down to confidence, mine in myself and his with himself. Check out style.com kids and the photo's from the recent Costume Institute Gala at the Met, many a man with a tall well heeled woman!

Good luck!

If you want to make a good first impression- heels. If you want to appear consistent go with flats. There are so many types of heels, don't go with screw me heels, pick an artsy pair that show your personality, a classic pump, or a strappy summer sandal or comfortable wedge. And go casual with the rest of the outfit and styling...

i think flats are better for the first date. it makes you seem a lot more laid back but still pretty. i mean, unless you're going to a crazy nice place for dinner or something i say flats all the way.