Women's advice requested: heels and jeans

[wayne0789456]

Is this for a first date? If so, they probably just don't want to go to a fancy place for a first date and made up an excuse.

 

Not always, sometimes this is after several dates.

[wayne0789456]

Are these first meets?

 

Those are good questions.

 

Not always first meets, but generally within the first month, generally by the fourth or fifth date.

 

Are they familiar with the venues and dress?

 

In some cases yes, and if I can't find something to compare it to that we both know of, I mention the cloth napkins, tablecloths, ambient lighting, and describe attire as "still somewhat casual, dressy but not formal attire." or something like that.

 

What do you typically wear?

 

That's a good question, the more I think about it. Thank you for asking.

 

It now occurs to me, I hardly ever wear blue jeans on dates. I don't think I intentionally avoid them, but now that you mention it I do tend to pass them over. Something extremely extremely casual like a nature walk might be a t-shirt, black denim shorts or black jeans, and New Balance running shoes. A more "typical" casual date may be a polo shirt with khakis or black or tan jeans (or equivalent shorts) and penny loafers or non-gym-shoe casual footwear (e.g boat shoes). The dressier dates would be a polo or button front shirt (no tie) with trousers (or equivalent shorts, I have had some trousers made into shorts for the summer) and dress shoes. Even on some casual dates I'll show up in a polo shirt, trousers, and casual footwear.

 

Is it you like heels or better dressers or you're a leg man?

 

Yes, I like heels, but I like flats, too. In other words, heels can look great, but heels are not required to look great.

 

Yes, I like better dressers, as I am sure most guys do. I always compliment my date when I like her outfit.

 

If liking skirts and dresses makes me a legman, then I suppose I am, but I do like casual pants and dress pants, too. These outfits can be quite beautiful. Feel free to take that comment any way you wish.

[wayne0789456]

I think dark washed jeans with heels and a nice blouse is one step below business casual and I like it for mid-range restaurants or first dates.

 

Flats can be dressy, but heels are more attractive. Heels make your legs and butt look better, it's just a fact.

 

The heels I will wear with jeans are usually kitten heels or just generally more casual. My heels for dresses/skirts are typically 3" high and can, in fact, be quite uncomfortable. And there are other considerations, too. If I wear dress pants on a date, I feel... too work-oriented? Maybe? But jeans, not so much. But wearing a skirt or a dress can present risks on a date. Say the date went great and you want to go for a walk afterwards. If it's windy, it can be uncomfortable.

 

Some interesting comments here. May I expand?

 

Not a criticism, just a question...how does business casual cause you to feel, to cause you to go right up to it without being business casual outright, like you described? Is it the work-oriented thing?

 

What if you knew that your date likes work-oriented clothing...would that be a consideration for you?

 

In light of the "risks" you perceive of wearing a skirt, is there ever a date on which you would wear a skirt? I hope that question isn't too specific, it's just that I am sure some others see things the same way as you, and I can't learn if I don't ask.

[LoveSoDeep]

I used to wear heels ALL THE TIME. I'm 5'1" and it was easier to just wear heels than to get every darn pair of jean I buy altered.

 

That being said, now that skinny jeans seem to be here to stay I can just roll up the bottom and wear flats and I'm all for it....just not usually not he first date. Heels make me feel sexier somehow...even if I am wearing them with jeans. On a first date I need to feel my best so I can be myself. I'f I'm worried about how I look then I'm likely to act a bit off (from the guy's perspective). So I go with what makes me feel good about myself. My choice in clothing really has very little to do with what I think the guy will like or what will impress him. My hope is that he will like me and be impressed by me; by who I am. My best chance at showing him who I am and seeing if that's his reaction is if I feel comfortable in my own skin and attractive....for me heels make me feel that way (even if they do hurt my feet a little).

 

My guess is if she resists going to a place where heels might be more acceptable (but wears them to work or at other times) maybe she' trying to prove she's not the "High Maintenance" type who wear heels 24/7.

[wayne0789456]

My guess is if she resists going to a place where heels might be more acceptable (but wears them to work or at other times) maybe she' trying to prove she's not the "High Maintenance" type who wear heels 24/7.

 

Your post has some intriguing comments. This one in particular sparked an idea.

 

Instead of dropping the idea of the nicer place permanently forever, would you suggest bringing it up again after a few dates, to give her the chance to "prove" that she's not high maintenance?

 

However...

 

If a date uses the "heels are uncomfortable" excuse to not go someplace nice, would I be out of line if I said something like, "Do you own any flats? They are just as nice and the restaurant does not require heels."? I've never done that before. Would that come across as controlling? I have no desire to control what a woman wears, or anything else. I would like to go to nice places a little more often, but I don't want to force her into it, either. That's no fun. Enjoying her company is the most important thing.

[surfdiva]

For me, it's the whole outfit. When I'm wearing my skinny jeans with heels, I'm usually wearing a cute/fun top that's comfortable.

 

When I'm wearing those same heels with a skirt, the skirt is probably a little uncomfortable with a blouse tucked in...that (for me) is what's uncomfortable. It's not the heels, it's the outfit (again, for me)

 

**But then again, 99% of the time I'm wearing flip flops

[Hermes]

Don't go there Wayne.

 

I can't think of any restaurant that actually requires heels. L.

 

I've worn skirts/dresses forever. It isn't a problem.

 

Some people want to wear jeans and nothing but, well it is their choice.

 

However, the matter here seems to be the go to nice places/not go to nice places argument, not the clothes. Yes?

[lilypadgirl]

In other words, my observation has been the majority of women indicating that heels are uncomfortable, AND the majority of women indicating that they don't feel dressed up if wearing flats, AND the majority of women actually wearing heels with blue jeans. If all three are the majority there has to be some overlap; the fact that two of these three are contradictory is what I hope to understand.

 

Haha, I know what you mean. I think that comes down to for most girls, flat are obviously more comfortable, but that doesn't mean we always just stick with one style. Sometimes, in the right mood, I'm willing to wear heels (or other fashion choice). Same with guys right, you have different styles that you prefer and wear more commonly, but will change it up given the right mood or event.

 

one even wore (on a first date) a nice top with a blue denim skirt and New Balance shoes for mini-golf and a casual dinner, and she really looked lovely Yes, I complimented her on choice of outfit.

 

Cute, I have to keep that one in mind!

 

Now my follow-up questions.

 

I know you can't speak for anyone else, but for you, are the heels the only things that can allow you to feel "sexy"? What about flats, with jeans of a different color (same denim material, a different color only), or khakis, or dress pants, or a casual skirt?

 

Would it change the way you feel if you knew that they guy thought flats looked attractive on you?

 

No, heels aren't the only thing that makes me feel sexy. But it's an easy way to spruce up a "normal" outfit. Of course, I do wear other outfits that I consider sexy/cute/fun, etc. Comes back to many different fashion styles - heels just being one of them. I would definitely appreciate it if a guy thought flats looked attractive on me. But, I don't think it changes my decisions to wear heels that much - mainly cuz I wear flats most of the time anyway. But I wear what I wear for me more than the guy (except maybe at the beginning of a relationship). Some days, I'm just in a heels mood. Heels also changes the way I walk, it naturally makes my hips sway and my legs look longer. And, as silly as this sounds, sometimes I just like to hear the clicking sound they make. So it's a different look/feeling/experience.

[JohnnyFranks]

People are dressing sloppy more often. Seems to be the normal.

 

I see alot of woman dress to the 9's for the office, and then dress real sloppy on the weekends. I don't get it either.

[Wiseman2]

Is that coming up in the conversation for the first meet or second date? Why don't you just come out and tell them you have a thing for high heels it's a pretty common fetish? Because this has nothing to do with date venues and attire.

If a date uses the "heels are uncomfortable" excuse to not go someplace nice.

[wayne0789456]

However, the matter here seems to be the go to nice places/not go to nice places argument, not the clothes. Yes?

 

Yes, I do like to go to nicer eateries, not all the time, but maybe 50/50, with a very occasional formal, instead of the 80-90% casual as has been the trend. It never occurred to me that clothing of any kind would ever be an issue; if the restaurant is higher end "casual", or it could be, then I dress up. I never envisioned that this required any thought, within reason. I would not plan a fancy restaurant and a nature hike together LOL. I can respect a woman's feeling toward heels, but when the same heels are the go-to footwear for the most casual of casual outfits, it was time to ask. Then, the idea that many feel they can't dress up in flats even though they would be as dressy in reality, so therefore all they can do is be very casual...well, bottom line, I had to ask, I had to learn, as the clothes (footwear) has been expressed as the barrier to going to nicer restaurants. I want to share this interest with a date / girlfriend.

 

Since you mentioned it, is there a way of possibly discussing this up front, so they get to know this side of me? I very much would like to find a woman who is like me in wanting a mix of very casual and upper end casual restaurants, who doesn't give a second thought to the attire and can just as easily go dressy as casual.

 

I have learned a lot in this thread, BTW, and as long as advice continues to be offered I will continue to consider it and digest it. I do understand a few things that I did not completely before.

 

Yes

[wayne0789456]

Is that coming up in the conversation for the first meet or second date? Why don't you just come out and tell them you have a thing for high heels it's a pretty common fetish? Because this has nothing to do with date venues and attire.

 

There is no fetish here with heels specifically. Yes, there is a slight preference for heels all things equal, I don't think it would be normal for me to not notice LOL, but honestly flats with tan jeans, for example, look a little better to me than heels with blue jeans.

 

But the point isn't what a date wears specifically, it's the idea that I can't share nicer restaurants with dates because they use shoes as a barrier, and I need the insight into the thought process.

 

I'll say it this way...if I met someone who is like me in dressing up for nicer venues without giving it a thought, yet never ever wore heels and only wore flats, I'd be ecstatic (at least on this topic)!

[HeartGoesOn]

Is that coming up in the conversation for the first meet or second date? Why don't you just come out and tell them you have a thing for high heels it's a pretty common fetish? Because this has nothing to do with date venues and attire.

 

I agree 100%....

[wayne0789456]

People are dressing sloppy more often. Seems to be the normal.

 

I see alot of woman dress to the 9's for the office, and then dress real sloppy on the weekends. I don't get it either.

 

Although somewhat off topic, I have to express my agreement. For me, I'm tired of the flip flops, but I can't really criticize to someone's face. I do offer compliments, though, when another sandal style is worn.

[wayne0789456]

I agree 100%....

 

Note what I said in the post immediately before.

 

There is no fetish here with heels specifically. Yes, there is a slight preference for heels all things equal, I don't think it would be normal for me to not notice LOL, but honestly flats with tan jeans, for example, look a little better to me than heels with blue jeans.

 

But the point isn't what a date wears specifically, it's the idea that I can't share nicer restaurants with dates because they use shoes as a barrier, and I need the insight into the thought process.

 

I'll say it this way...if I met someone who is like me in dressing up for nicer venues without giving it a thought, yet never ever wore heels and only wore flats, I'd be ecstatic (at least on this topic)!

[MatchMystified]

Many dates have been averse to going to places (e.g. restaurants) where somewhat dressy attire, not formal attire, but business casual or smart casual, nothing extravagantly fancy in attire, but just a step or two above usual casual. A major reason given is often that heels are uncomfortable.

 

I can completely respect that. However...

 

...the same women often wear the same heels they indicated to be too uncomfortable, with blue jeans, on their own, even when there is no reason to wear heels.

 

...then, secondly, it doesn't occur to many women to wear flats if heels are too uncomfortable. Heels can look awesome, but so can flats.

 

Several questions:

 

1) How are the same heels too uncomfortable to wear with something nice like jeans of a color other than blue, or even a casual skirt, perfectly comfortable with blue jeans?

 

 

2) Why do many women perceive flats to be not dressy?

 

3) Why does it seem that the go-to attire is dressing up the shoes and leaving the blue jeans in tact, rather than going for more comfortable footwear and dressing up the jeans / pants / bottom?

 

Can some women educate me on this topic? Thanks.

 

 

It depends on the woman and her shoe preference. Heels / pumps + the jeans + cute top are in fashion. Flats are not dressy and personally they make me feel dowdy. Wedges are awesome because they offer stability and are sexy depending on the shoe.

 

Also, about the dressy attire question - I have professional office attire and jeans. I don't really have stuff "in-between" that would be dressier than my professional wardrobe. Maybe that's what other women are experiencing also. Hope that helps.

 

-MM

[notalady]

Yes, I do like to go to nicer eateries, not all the time, but maybe 50/50, with a very occasional formal, instead of the 80-90% casual as has been the trend. It never occurred to me that clothing of any kind would ever be an issue; if the restaurant is higher end "casual", or it could be, then I dress up. I never envisioned that this required any thought, within reason. I would not plan a fancy restaurant and a nature hike together LOL. I can respect a woman's feeling toward heels, but when the same heels are the go-to footwear for the most casual of casual outfits, it was time to ask. Then, the idea that many feel they can't dress up in flats even though they would be as dressy in reality, so therefore all they can do is be very casual...well, bottom line, I had to ask, I had to learn, as the clothes (footwear) has been expressed as the barrier to going to nicer restaurants. I want to share this interest with a date / girlfriend.

 

Since you mentioned it, is there a way of possibly discussing this up front, so they get to know this side of me? I very much would like to find a woman who is like me in wanting a mix of very casual and upper end casual restaurants, who doesn't give a second thought to the attire and can just as easily go dressy as casual.

 

I have learned a lot in this thread, BTW, and as long as advice continues to be offered I will continue to consider it and digest it. I do understand a few things that I did not completely before.

 

Yes

 

I like to go to nicer (below fine dining but above casual) restaurants too, in addition, I like to try new restaurants, the way I distinguish if someone has the same interest as me is easy. The topic of food generally come up in the first few dates, I would generally ask and discuss what their preferences are (what cuisine etc), I would tell them what I like and where I enjoy going to. I would also add that I like to try new places. They would then make some kind of comments that would tell me if they are the same.

 

If I were you, I would arrange for dining at a nicer restaurant for the second or third date. If they refuse then I would ask if they generally don't like to go to nicer restaurants and figure out if it's just this once or ongoing. Then you can decide if you want to keep dating them.

[Wiseman2]

Never heard of that. If you tell them where you're going, it's doubtful they are clueless enough to show up in flip-flops.

I can't share nicer restaurants with dates because they use shoes as a barrier

[wayne0789456]

Also, about the dressy attire question - I have professional office attire and jeans. I don't really have stuff "in-between" that would be dressier than my professional wardrobe. Maybe that's what other women are experiencing also. Hope that helps.

 

That sounds logical. Would you mind if I asked a few questions? Just to understand further. Some others are like you I am sure.

 

What do you do when going to a nicer restaurant? Or, are you the type to refuse them? Then, do you refuse them by choice, or would yo enjoy them and you refuse them because your wardrobe does not contain the proper attire?

[wayne0789456]

If I were you, I would arrange for dining at a nicer restaurant for the second or third date. If they refuse then I would ask if they generally don't like to go to nicer restaurants and figure out if it's just this once or ongoing. Then you can decide if you want to keep dating them.

 

That sounds like a good idea. I tend to drop it right away, so as not to come across as trying to force them into doing something they don't enjoy, but I must be going too far the other way.

 

I guess that's a good way of getting the truth next time a date uses dislike for heels as an excuse not to go to a nicer restaurant.

[MatchMystified]

That sounds logical. Would you mind if I asked a few questions? Just to understand further. Some others are like you I am sure.

 

What do you do when going to a nicer restaurant? Or, are you the type to refuse them? Then, do you refuse them by choice, or would yo enjoy them and you refuse them because your wardrobe does not contain the proper attire?

 

I would wear one of my nicer work appropriate items and bump it up with jewelry. If I didn't feel comfortable with my existing wardrobe I would go out and purchase something so I felt comfortable in my attire for that event. I wouldn't refuse, I would plan ahead so I knew what I was wearing and also that I was confident in my attire.

 

Did something happen with a special lady friend because I'm sensing a deeper question here?

[wayne0789456]

Did something happen with a special lady friend because I'm sensing a deeper question here?

 

That's nice of you to ask. Thank you.

 

It's not so much a single bad experience, or even a bad relationship, but more a build up of...I guess frustration. Dinner out is a favorite activity of mine, and I become interested when a new restaurant opens up. If I happen to be in an area that I do not visit that often, I'm always noticing the restaurants. When it comes time to pick one, I find myself trying to seek out the one or two or three that appear to be the classiest.

 

In the same way that I wish to share my other interests with my date, and her with me, I would like to share this one, as well. I've dated several people over the last...2-1/2 to 3 years, and 100% of them has wanted to stay with casual atmosphere, like Olive Garden or Applebee's level, except for maybe 2 or 3 times a year, and then only to obligatorily celebrate a milestone or something, not because she finds it fun. While I do genuinely want to go to a casual restaurant like that 50% of the time, I would enjoy nicer restaurants the other 50%.

 

When I suggest a nicer restaurant, usually by the third, fourth, or fifth date, a common reason given is that heels are uncomfortable, but they are worn to the casual restaurants...which ultimately prompted me to start this thread, to hope to learn this side of women, what they are actually thinking.

 

It's been suggested that I should just go to the nicer restaurants by myself, but isn't a part of relationships sharing each other's interests? I don't feel right EXcluding her from this major one of mine, especially since it is a date activity to begin with. Then, what about in a marriage situation. It just doesn't seem right to me.

 

You sense something deeper. I've learned that women's intuition is a good thing to pay attention to, so I am definitely listening. I'll be glad to provide more information if needed.

 

BTW, for a date to go out and specifically purchase an article of clothing for a date would make me feel bad, especially if she had other financial goals...unless creating a "date wardrobe" for herself is one of them, and it doesn't get in the way of something longer-term.

[MatchMystified]

 

When I suggest a nicer restaurant, usually by the third, fourth, or fifth date, a common reason given is that heels are uncomfortable, but they are worn to the casual restaurants...which ultimately prompted me to start this thread, to hope to learn this side of women, what they are actually thinking.

 

BTW, for a date to go out and specifically purchase an article of clothing for a date would make me feel bad, especially if she had other financial goals...unless creating a "date wardrobe" for herself is one of them, and it doesn't get in the way of something longer-term.

 

I think the person who told you the "heels are uncomfortable" excuse is lame. I think it sounds like they just don't want to go. It's not a requirement to wear heels to an upscale restaurant.

 

As far as purchasing date clothing, that's more about me. I want to feel confident, comfortable and appropriate. So yeah I would purchase a nice top or whatever to feel awesome.

[wayne0789456]

It just occurred to me, early conversations on restaurants are generally about cuisine. I'm starting to think that I should ask if she has a preference on the atmosphere before we go out, and then consider that as one of the personality traits on which to decide if I want to go out with her to begin with. I already pass up potential dates because they don't enjoy som e of my favorite activities, perhaps this should be one of them????

 

I usually suggest a casual place for a first date, but it's the first time I suggest a nicer place that I get the "I don't feel like wearing heels" or similar response, from those who respond that way. But, then, two ot three weeks later, they show up in the same heels, with blue jeans, to a casual establishment. Whatever, I guess.

 

Maybe I just need to communicate better up front. Although, the next woman who immediately goes for the "I don't like heels" response, I'm definitely suggesting that she does not need them and flats are acceptable. I have nothing to lose.

[Wiseman2]

Flats being acceptable to you or the venue? There is absolutely nowhere on earth no matter how fancy/expensive that requires women to wear heels. This seems like your need/requirement, but you use the veil of 'elegant dining' to engage in a convo about footwear.

the next woman who immediately goes for the "I don't like heels" response and flats are acceptable.