Women's advice requested: heels and jeans

[wayne0789456]

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.

[Gloworm]

I almost never wear heels. I love my dressy flats and mary janes.

[wayne0789456]

Do you have a problem stepping up the pants to something a little nicer with those flats, to go to a little nicer place?

[Gloworm]

Id love a guy to take me somewhere nice. You see im a tad chubby and only have a couple jeans that work for me right now.. So i actually dont have any dress pants that fit. I wouldn't mind wearing a nice skirt or dress tho.

[Gloworm]

I need a new wardrobe actually haha. Im also petite so its hard to find clothes for me.

[browneyedgirl36]

I gave up heels a couple of years ago -- they were starting to wreck my feet. Now, it's flats, flat sandals, or VERY low-heeled boots or wedges for me.

 

I'm not into the jeans-with-heels thing at all. I will wear jeans with flats or with boots and a nice blouse, but for a really nice, dressier place, I will wear at least a casual dress or skirt. As rule, I don't really wear pants (except for jeans, sometimes) because it's hard for me to find pants I like that fit (I've got short legs, and everything is really long on me!)

 

Heels look nice, but for me, they're not worth the damage they've already done to my feet (i.e. my feet hurt most of the time, even when I'm wearing comfortable shoes!)

[Theniceone]

Bizarre, refusing an outing because of shoes?? Are we talking a first date here? Could it be possible that these women are not comfortable being wined and dined early on an come with lame excuses as this? Or they simply do not like to dress up and do not want to wear dressy pants or don't own any.

 

Personnally, i dress for the occasion and if I want to wear a nice pair of heels, i bring those cheap bendable flats that i carry in my purse so i do not let my shoes ruin what could be a great evening.

 

BTW, I do not think there is any reason to wear heels or not. It is a personal choice, so I can wear heels to go to the grocery store, or wear sneakes or flats. All would depend on my mood , the level of comfortness of the shoes chosen and how much walking I plan to do that day.

[wayne0789456]

Bizarre, refusing an outing because of shoes?? Are we talking a first date here? Could it be possible that these women are not comfortable being wined and dined early on an come with lame excuses as this? Or they simply do not like to dress up and do not want to wear dressy pants or don't own any.

 

Personnally, i dress for the occasion and if I want to wear a nice pair of heels, i bring those cheap bendable flats that i carry in my purse so i do not let my shoes ruin what could be a great evening.

 

BTW, I do not think there is any reason to wear heels or not. It is a personal choice, so I can wear heels to go to the grocery store, or wear sneakes or flats. All would depend on my mood , the level of comfortness of the shoes chosen and how much walking I plan to do that day.

 

Maybe I was unclear, whole outings aren't "refused", the questions in my thread are regarding a general concept that a lot of women say they don't like dressing up because of heels, they'll go for a completely different far more casual outfit rather then wear flats they own, even though they don't mind the flats. At the same time, the same heels that cause them to dislike dressing up are often the default footwear with blue jeans. That is what I don't understand.

 

You have a point about the first dates vs. later on. I haven't noticed a correlation, not that I have looked for one, either. I learn as much of her likes and dislikes in activities and restaurants before the first date and try to pick something we both like.

 

This is not something I am "dissatisfied" about. I have never brought it up to any of my dates nor will I likely ever. Heels can look awesome but if she does not like them I would never expect to wear them. I just find that the above described "quirk" is present in a lot of women, so it can't be much of a quirk. I am simply curious as to why the same women who dress up as little as possible because of heels, default to them for a bottom so casual, and avoid dressy outfits altogether before substituting flats (when they own them) for the heels.

[Hermes]

I just don't know Wayne. Some kind of fad I suppose, the thing about heels with jeans.

 

I love my high heels (thought I wear boots or flats if the weather or occasion requires). When I say high heels I do not mean those crazy six inchers. Anyhow the stores here are FULL of high-heeled shoes so someone is buying them. I'm another person when in my black suede high heels lol.

My feet are great, so no problems caused by the high heels. However, it is all down to the quality of the shoe, high or otherwise. As always, you get what you pay for.....

 

I have always worn dresses (not just for "occasions"), but the dresses are geared to day to day, occasion, more casual, weather etc.

The only trousers I have got are disreputable and worn when gardening or country walking.

 

I often look around me with dismay and see all these women wearing exactly the same drab garb, as if it was some kind of required uniform in a dismal dictatorship state. Don't understand it.

[TMifune]

Wayne,

 

I get it.

 

If heels are too uncomfortable to wear with "nicer" clothes, why aren't they too uncomfortable to wear with blue jeans?

 

I think you need to step back and look at more. The uncomfortable thing is an excuse and also true. I'm fairly certain that heels are relatively uncomfortable, but women will embrace the discomfort to make an impression in certain situations. My guess would be that the women wearing heels with jeans are looking to make an impression with you, while the women refusing to go to a nicer place are actually less interested in making an impression.

[wayne0789456]

I'm another person when in my black suede high heels lol.

 

That is an interesting quote, and it led to a theory. Could I run it by you?

 

Are you saying that shoes, of any kind -- heels, flats, boots, sandals, whatever -- have nothing to do with dressy or casual? Is it possible that the heels are not for how they look but how they feel? Is it possible that the aversion to dressing up is not for the shoes but for the rest of the outfit? But, then again, if so, why am I lied to so frequently?

 

How about you, specifically, what is it about those black suede heels that makes you feel different? And does that apply regardless of the rest of the outfit?

 

Am I extrapolating too far or am I in the neighborhood?

[Hermes]

Heh heh Wayne.

 

Dunno, I love black suede. Or suede anyway. Now I would wear those when dressed up (in a dress I hasten to add, or a skirt suit). But I also have high-heel sandals (not skyscrapers) just high heels and I wear them quite a bit.

People have actually asked me where I got those shoes. Got them on my travels.....

 

I don't understand the fixation with trousers. I have seen some ladies I know who always wear trousers and yet I've seen them in a dress and they looked so lovely.

 

A problem I think, is that some do not know HOW to dress, and less so how to dress for an occasion and do not understand that "less is always more", in the sense of keep away from the fussy stuff...bows, flounces, frills...

Maybe that is the problem, so the dreaded trousers are somehow "safer".

 

The only woman I know who could wear trousers (and she didn't all the time) was Marlene Dietrich. In a film (a very old one) she was dressed in a man's dress-suit (you may perhaps refer to it as a tuxedo), and oh boy was she something.

But, that was her...

 

Some women have said to me (believe it or not!) that it is too much trouble to wear a dress/skirt as they can't (read, don't know how) get the look together. Or they end up with the "Christmas tree" look. Simplicity is always best.

[Snny]

I find heels with jeans a very tacky sense of fashion. Like a person can afford a nice pair of classy shoes, but HAS to mismatch them with blue collar class jeans? Ewe. If I'm going to wear heels or flats, it looks better with dressy trousers, skirts, or dresses.

 

If you're gonna dress with class, don't show any trash. Make it match, darling.

 

Only fashionable footwear with jeans:

* Flip-flops (there are fashionable ones out there! You just have to look)

* Sperry's (personal fave, highly recommend)

* Casual boots (only with jeggings or tight jeans).

 

I save my sneakers for the gym/track.

 

I'm a snob, dont care. Just my HO

[reinventmyself]

I am probably of no help here. I dress up daily for work, so getting dressed up socially is not a novelty.

You'll likely find me happy in my jeans and flip flops on weekends. . I do love my boots too, but without a heel.

 

I will dress up begrudgingly if need be.

 

Heels and jeans. . Uhm, not so much. I am glad my boyfriend is tall because I often prefer not to be the tallest woman in the room either.

Tall people tend to stand out of the crowd. I prefer to not draw unneeded attention to myself. I am just that way.

 

I did go out with friends recently wearing the `jeans and heels' Two strangers came up to me and commented on my height. Come on, now!

I am not that tall.

[abitbroken]

When I dress up to go out on the town, it is different than dressing for a board meeting. Nice jeans, preferably a good name, with fun shoes - heels, platforms, sexy boots, etc, a nice or fun handbag, etc, and a top that is a lot nicer than what is normal with kick around jeans or a fun jacket/blazer is what I wear. If I am going to a funeral, I wear a suit or a dress. If I go to a meeting, I wear a suit.

 

There is a difference between wearing pumps/conservative shoes that are seen as "dressy" vs fun shoes that are heels that are not considered conservative - I have high heels that have a better footbed than "dressy' shoes. I have platform pumps that are super cute and fun and are way more comfortable than "dressy" shoes.

 

Honestly, I would go to those nicer places and let your date choose what to wear and if you get asked to leave - go somewhere else. Maybe she will change what she wears if she checks it out and sees what others are wearing are not business suits. If a woman is in dark jeans, high heels, and a nice top or blazer - they are not going to kick her out. If she wore light blue jeans with the knees out, sneakers, they would (?) I have seldom seen anyone get asked to leave or not gained admittance unless they were wearing shorts, flip flops, a bikini top, or something that doesn't cover.

 

Also, complimenting someone when they wear something that you DO like goes farther.

[mustlovedogs]

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.

[Hermes]

Not a chance, MLD. All my dresses are shift-style or sheaths. No way will they lift in the wind heh heh

 

Could I add one thing: please, please do it for me, do not wear what is called a "blazer" (here called a jacket) with a nice dress. You only end up looking like a quarterback.

[Wiseman2]

Are these first meets? Are they familiar with the venues and dress? What do you typically wear? Is it you like heels or better dressers or you're a leg man?

Many dates have been averse to going to places (e.g. restaurants) where somewhat dressy attire

[lilypadgirl]

Have you seen both quirks in the same girl? That is, has the same girl who doesn't like to wear heels to a fancy dinner out then wear heels with blue jeans?

 

I ask because my first thought is maybe it's just personal choice - some girls like heels and some don't and given that jeans and heels is a fad, you're going to see the girls that like heels wear them with jeans.

 

If you see it with the same girl, then depending on the circumstance, it could be an excuse to not go out or simply different moods dictate different footwear styles.

 

Personally, I prefer flats as they are more comfortable and wear flats 80% of the time, but sometimes I like to dress up a little but without being too dressy. So heels with jeans allows me to feel sexy but still dress comfortably/casually.

[ParisPaulette]

Well, for one thing heels with jeans, if done right, can look really good on a woman. And jeans are a uniform for many women, it's what gets worn all the time so it just sort of becomes second nature. I can count on one hand the number of times I've worn a dress in the last year, dress pants too. It's nearly always jeans, because I work from home, own horses, live on a ranch and live in an area that is rural enough that at any given hour a storm, the brush and other flora and fauna or yes the occasional scorpion or snake could ruin the hell out of any dress I'd be dumb enough to put on. For the record when I dress up I wear my jeans with boots, really nice expensive cowboy ones, and a silk shirt. Occasionally I will wear formal long dresses with low heels for major events like an art gallery opening, that's about it. My high heels days long ago passed me by and I was never that crazy about them to begin with.

 

That said I'm not sure where you're getting your info from, because I still see massively more women wearing heels with dresses than I do heels with blue jeans. This sounds like a personal preference and it's probably partially to do with what the woman in question likes to wear and what she feels comfortable wearing.

 

For the record maybe she's like me and finds it a whole lot harder to navigate and stay modest in a dress than in blue jeans. Shoes can always be kicked off or in certain shoe styles are comfortable enough one doesn't really think about it. Some women are even yes used to heels and comfortable enough in them to not really have an issue with moving about. But wearing a dress can be really uncomfortable in so many ways with it hindering movement if it's long enough, causing anxiety that too much will be exposed if it's shorter.

 

At least if you fall on your face wearing heels in blue jeans you don't flash the world. There's something to be said for that. So maybe she's like that too or feels like that.

[notalady]

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.

[Sportster2005]

People will dress anyway they want, with reasons only they need to know.

 

If you don't like the way a person dresses for dates, they're just not a good match for you.

[Brokenheart99]

I wear heels with jeans all the time, especially on first dates. Ordinarily outside of dates and somewhere nice, I don't dress up or wear heels because it's uncomfortable. This is the question you are asking I imagine, why?

 

Couple reasons, I really hate dresses and skirts, they don't flatter my figure and I just don't like wearing them much. Heels make me feel pretty and look nice when worn with jeans. Plus wearing heels with jeans is casual yet kinda fancy. So you don't look like you're trying too hard. And since it's a date, I want to look a little nicer and look my best so I do it. It's not always super comfortable but I do it.

[wayne0789456]

Lilypadgirl, very insightful post. Thank you. Could I ask a few questions to expand and to better understand this?

 

Have you seen both quirks in the same girl? That is, has the same girl who doesn't like to wear heels to a fancy dinner out then wear heels with blue jeans?

 

Sometimes, but mostly its an overall observation. 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.

 

In a few cases I have noticed both in the same person. Usually, they "show up" several weeks after indicating that heels are uncomfortable in heels and blue jeans; 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.

 

Personally, I prefer flats as they are more comfortable and wear flats 80% of the time, but sometimes I like to dress up a little but without being too dressy. So heels with jeans allows me to feel sexy but still dress comfortably/casually.

 

Interesting statement. It sounds logical.

 

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?

[wayne0789456]

I wear heels with jeans all the time, especially on first dates. Ordinarily outside of dates and somewhere nice, I don't dress up or wear heels because it's uncomfortable. This is the question you are asking I imagine, why?

 

Couple reasons, I really hate dresses and skirts, they don't flatter my figure and I just don't like wearing them much. Heels make me feel pretty and look nice when worn with jeans. Plus wearing heels with jeans is casual yet kinda fancy. So you don't look like you're trying too hard. And since it's a date, I want to look a little nicer and look my best so I do it. It's not always super comfortable but I do it.

 

So, in other words, if I understand you properly, you're willing to deal with that one single uncomfortable item if the rest of the outfit is very comfortable. It sounds as though you are saying that wearing dress pants, or khakis, or jeans not blue, for you, is more uncomfortable than wearing the heels.

 

Do you feel pretty in flats and a different pant style? Or less so than the heels and blue jeans? Or should I refer to my comment in the above paragraph?

 

Am I in the ballpark on my understanding of your comments?

 

I wear heels with jeans all the time, especially on first dates. Ordinarily outside of dates and somewhere nice, I don't dress up or wear heels because it's uncomfortable. This is the question you are asking I imagine, why?

 

Couple reasons, I really hate dresses and skirts, they don't flatter my figure and I just don't like wearing them much. Heels make me feel pretty and look nice when worn with jeans. Plus wearing heels with jeans is casual yet kinda fancy. So you don't look like you're trying too hard. And since it's a date, I want to look a little nicer and look my best so I do it. It's not always super comfortable but I do it.

 

I wear heels with jeans all the time, especially on first dates. Ordinarily outside of dates and somewhere nice, I don't dress up or wear heels because it's uncomfortable. This is the question you are asking I imagine, why?

 

Couple reasons, I really hate dresses and skirts, they don't flatter my figure and I just don't like wearing them much. Heels make me feel pretty and look nice when worn with jeans. Plus wearing heels with jeans is casual yet kinda fancy. So you don't look like you're trying too hard. And since it's a date, I want to look a little nicer and look my best so I do it. It's not always super comfortable but I do it.

 

I wear heels with jeans all the time, especially on first dates. Ordinarily outside of dates and somewhere nice, I don't dress up or wear heels because it's uncomfortable. This is the question you are asking I imagine, why?

 

Couple reasons, I really hate dresses and skirts, they don't flatter my figure and I just don't like wearing them much. Heels make me feel pretty and look nice when worn with jeans. Plus wearing heels with jeans is casual yet kinda fancy. So you don't look like you're trying too hard. And since it's a date, I want to look a little nicer and look my best so I do it. It's not always super comfortable but I do it.

 

I wear heels with jeans all the time, especially on first dates. Ordinarily outside of dates and somewhere nice, I don't dress up or wear heels because it's uncomfortable. This is the question you are asking I imagine, why?

 

Couple reasons, I really hate dresses and skirts, they don't flatter my figure and I just don't like wearing them much. Heels make me feel pretty and look nice when worn with jeans. Plus wearing heels with jeans is casual yet kinda fancy. So you don't look like you're trying too hard. And since it's a date, I want to look a little nicer and look my best so I do it. It's not always super comfortable but I do it.