Dressing up for dates

[Wayne0789456]

I have a multi-part question at the end of this post. To start, some background.

 

I like to dress up on dates, and would like to do so for more of them, but most of the women I date have wanted to avoid this, reasons given include things like feeling limited in what they can do in anything other than the most casual attire (like blue jeans), or feeling like it’s pointless, or finding heels and flats uncomfortable, and other things like that.

 

However...

 

I was at a walk-through botanical flower garden the other day (not on a date), but noticed dozens, literally dozens, of women wearing nicer attire, and / or HEELS!!! Walking, often for a couple of hours continuously, doing one of the most casual activities that exists. Not every woman was wearing blue jeans and tennis shoes. Obviously, many women do find dressy attire (including heels) comfortable.

 

A few specific examples of casual, dressy, and in between outfits I remember seeing. I saw a woman wearing a dressy top with mint green jeans and heeled ankle boots; one wearing black jeans with flats; khaki pants with stiletto pumps; a dress with blue tights and t-strap flats; a sweater with a dressy skirt, black tights, and flats; a dressy top with slacks and stiletto pumps; a dressy top with a red skirt, black tights, and pumps; and many more casual, dressy, and in-between outfits with heels that I cannot remember to describe. While most patrons obviously were dressed extremely casually, I am just making the point that women dressed up and in nicer casual attire (including heels) was also the norm, again, for one of the most casual activities there is to do.

 

I see women dressed up all the time, on dates, to other activities and places where there is no reason to do so, as well, even when the guy is very casually (and in some cases sloppily) dressed. She has put forth effort and he hasn't. The reverse seems to be true in my dating.

 

Some of my questions:

* Would it come across as shallow or controlling if I expressed my own preference for dressing up for dates, and with that my preference for a women who enjoys dressing to match?

 

* Is there a personality trait I should be looking for, that I perhaps overlooked, that indicates or goes hand in hand with her own preference for dressing up or dressing casually?

 

* What are some circumstances that would cause a woman to want to dress up like I described above for the most causal of casual dates?

 

* The most important qualities I look for are things such as a caring heart, personal responsibility, ambition, independence, common enjoyment of activities. Should I be including attire preference as one of the personality qualities I look for? How do I do this without sounding like her clothes are more important than her personality to me? Is general attire preference perhaps not as shallow as I think it is?

 

* What can I do in preparation for a date that would cause the woman to naturally see our date as worth dressing nice for?

[Grey40]

It's a pretty weird question. Why do you have to dress up for all your dates? Would it kill you to dress casual?

 

A lot of times people just don't want to invest that much effort, especially on a first date. Why would you dress up and waste time if you end up hating the person?

 

For women, it puts a lot of pressure on them to dress up. They feel they need to impress. They already worry and spend hours upon hours trying to figure out what to wear everyday, if you make them dress up for a date you'll probably never get them to actually go. Every single girl will flake on you guaranteed.

 

If you want to ensure that you can dress up, and that they most likely will too is to make the date going out to a nice dinner and semi-fancy place. Like I said, this tends to scare women off because it's just too "formal" and "serious" for someone they literally just met. The best date option is super casual, low key. If you want to get fancy on the second or third date, go for it.

 

Also, if you're the kind of guy that just likes to dress up all the time, that's fine too, but it all depends where you're going. You are going to come across as socially awkward if you're going to a pub or bar in a suit on a date.

 

So my suggestion is start learning to like dressing more casually, especially on first dates. You can go business casual--t-shirt, slacks, nice shoes, but I wouldn't be wearing anything more professional than that. If you MUST dress up, just be aware that you'll be going on far less dates and you'll have a lot of dates being canceled on you last minute due to nervousness and indecision.

[grays]

This is so interesting to me. I don't dress up at all period. There's never a time I'd rather be in heels than sneakers. I wear flip flops about 90% of the time. I appreciate a heads up if a guy is really into dressing up or having a woman dressed up for him. That's my cue that we are not meant for each other.

[Haydn]

A Cravat is a must. Preferably silk so she can run her fingers over it`s smoothness. (Pain to put on though, get a friend to help)

 

Riding Breeches. Make for a shapely leg...

 

Waist Coat. Always buttoned! (Obviously not one with vivid colours which could detract from the rest of the outfit and possibly make your date go blind)

 

Chunky Cuff Links are just the thing to enliven an evening. Always play with them. (Look like the secret secret service)

 

Braces, (Suspenders) Let one dangle off one shoulder casually as the evening gets more boozy.

 

Oxford Brogues. Just the thing if you are in the countryside. Or the date gets a bit soggy.

 

Gold pocket watch, only if you go with the `Top Hat` option. (Excellent for doffing at every opportunity)

 

Finally `Perfect the brood` (For the blokes) Say very little. Glower handsomely across the room.

 

Worked every time!

[GemmaUK]

None of the clothes you describe sound particularly dressed up to me, they sound more like ordinary daily wear and I wear boots as they're more supportive and comfortable but I can't recall the last time I just wore blue jeans and tennis shoes.

Wearing stilettoes for walking is a dumb and unhealthy idea though.

I know a few women who go from stilettoes to flip flops depending on the seasons and they have the worst feet, covered in hard skin and you can see the pain they are in at the end of the day.

I also know a woman who used to wear stilettoes all the time, she was told by her doc when she was in her mid thirties to stop wearing them or she would end up having to have her toes amputated.

 

I know many women who wear jeans and sweatshirts as daily wear and many who dress similarly to me.

Why don't you just go with seeing how they dress when you go on dates?

 

Yes it would sound controlling and shallow to specify that they dress a certain way.

[BaileyB]

Some women like to dress up, while others really don't.

 

Most, I think, would dress up for an occasion that would require nice dress... A nice dinner or a party. If you want a woman to dress nicely, invite her out for a nice date. It's not appropriate to dress in heels and a dress for a movie.

 

If you like how a woman likes when she is dressed up, compliment her. It is more likely that she will do it again if she knows that it is appreciated. Otherwise, it would be very controlling for a man to tell a woman how to dress.

 

Casual dress has become much more acceptable in society. High heels are not something that many women will wear. They hurt, they are uncomfortable, and they do terrible things to your feet.

[phineas]

As long as she isn't frumpy i can care less how a woman dresses for hanging out or regular dates.

[mikeylo]

Heels in a botanical flower garden ?

 

It's difficult to dress up all the time. What you can do is to go on dates and see if the woman you are dating is into dressing up all the time or not. You asking her is going to come out as controlling and shallow.

[Gaeta]

If you are online dating than just mention it in your profile.

 

I remember reading a profile where the man said he prefers a woman that keeps her nails long and professionally made. I passed that profile promptly and it saved us both time lol.

 

I like to dress up and look nice so I do if most days. I would never go out with my boyfriend without looking by best even if it's just grocery shopping. That being said I will not grocery shop in high heels. There is dressing up and there is common sense.

[preraph]

You can't tell a woman how to dress, period. Do not EVEN go there.

But I will tell you that I do sympathize. I think it's crazy how crappy people dress for dates these days. I remember making a lot of people on here mad in a thread about it here some years ago. I mean, you want to get the person's interest so doesn't it makes sense to present your best self on the first date or two?

 

Still, it's too controlling to tell someone that. All you can do is not take them out again, and that is what you should do.

 

Now, obviously, you tell the person before any date where you're going and the most you can do is say "it's okay to dress up there or not. I think I'll dress up a little." So you can say what you're doing to try to get the light bulb to go off, but don't tell her what to do.

 

As far as heels, they're impossible for anything except being dropped off near the restaurant door. They are not for going to a botanical garden. They hurt and they sink into any grass. However, there are dress shoes for such events, lots of them, from pretty flats to low wedges.

 

You're not going to be happy with a woman whose only shoes are athletic shoes or thongs, and there are plenty of those.

[Dis]

Theres a balance as Grey said

 

Theres a way of 'dressing up' thats appropriate for casual dates, you wouldnt want your date to be in a mermaid tale gown at a bowling alley right?

 

I absolutely LOVE to dress to kill (within reason for casual events) I wear stilletos the majority of the time. I absolutely never ever wear flats (unless at the gym..I'm also 5'1 so its cool ) For a casual date.... stilletos, jeans, a NICE shirt (not something frumpy) something form fitted yet causal, earrings (Big or small depending on the cut of my shirt), sometimes a necklace is my earrings arent overpowering, sometimes bracelets

 

I recently went out on a date to a bowling alley. I wore a white button up with a really stylin corset over it, dark high waisted jeans and of course matte black stilletos. Hair down in loose curls, half moon earring and one bangle on my wrist. Loved it and it wasnt too dressy but still looked fab! The bowling shoes not so much...but despite my looks I'm not high mantinence as in I cant put on bowling shoes, laugh have an awesome time!

 

I like to be a knock out but a knock out thats appropriately dressed, I'm not wearing a ballerina skirt to the movies

 

If I go out somewhere fancy, then its on like donkey kong!

 

I want to start a fashion thread now!!!

 

I would put something in your profile along the lines of, I'm looking for someone stylish, a woman whos not afraid to rock pumps on a casual night out

 

But other than that...you're just going to have to do the leg work

[spiderowl]

Personally, I'd wear what I felt was nice on me for a date and not dress up as you seem to be suggesting. I think it is a personal decision what one wears for a date. You cannot control what your date wears other than refusing to go out with women who do not dress up as you wish. Yes, a few will drop off their perches because for them dressing up feels superficial and unimportant. High heels are uncomfortable but some women like them. You need to find the kind of woman who feels dressing up is important to her. If you are lucky, you will find the other qualities you seek in a woman too.

 

I read profiles online and if a guy says he likes dressing up or that he prefers a woman who likes dressing up, I avoid them. I don't want to engage with guys who have a 'thing' about this. It is their 'thing' not mine. I am not likely to be compatible with them. I do not think people should turn up scruffy and unkempt but dressing up is a whole different league.

 

You should go for what matters to you. Yes, I would recommend that you tell the women you want to date that you would like them to dress up. Some of them will drop out and change their minds, but then, they are not the kind you like.

[losangelena]

I think you should feature photos on your dating profile that show you dressed up. Also, describe in your profile how important it is for you to look nice most of the time, and that it's important for your woman to do the same. That way you're less likely to attract women who prefer more casual dress. Likewise, look for women's profiles who are also dressed nicely in their photos.

[Simple Logic]

I have a multi-part question at the end of this post. To start, some background.

 

I like to dress up on dates, and would like to do so for more of them, but most of the women I date have wanted to avoid this, reasons given include things like feeling limited in what they can do in anything other than the most casual attire (like blue jeans), or feeling like it’s pointless, or finding heels and flats uncomfortable, and other things like that.

 

However...

 

I was at a walk-through botanical flower garden the other day (not on a date), but noticed dozens, literally dozens, of women wearing nicer attire, and / or HEELS!!! Walking, often for a couple of hours continuously, doing one of the most casual activities that exists. Not every woman was wearing blue jeans and tennis shoes. Obviously, many women do find dressy attire (including heels) comfortable.

 

A few specific examples of casual, dressy, and in between outfits I remember seeing. I saw a woman wearing a dressy top with mint green jeans and heeled ankle boots; one wearing black jeans with flats; khaki pants with stiletto pumps; a dress with blue tights and t-strap flats; a sweater with a dressy skirt, black tights, and flats; a dressy top with slacks and stiletto pumps; a dressy top with a red skirt, black tights, and pumps; and many more casual, dressy, and in-between outfits with heels that I cannot remember to describe. While most patrons obviously were dressed extremely casually, I am just making the point that women dressed up and in nicer casual attire (including heels) was also the norm, again, for one of the most casual activities there is to do.

 

I see women dressed up all the time, on dates, to other activities and places where there is no reason to do so, as well, even when the guy is very casually (and in some cases sloppily) dressed. She has put forth effort and he hasn't. The reverse seems to be true in my dating.

 

Some of my questions:

* Would it come across as shallow or controlling if I expressed my own preference for dressing up for dates, and with that my preference for a women who enjoys dressing to match?

 

* Is there a personality trait I should be looking for, that I perhaps overlooked, that indicates or goes hand in hand with her own preference for dressing up or dressing casually?

 

* What are some circumstances that would cause a woman to want to dress up like I described above for the most causal of casual dates?

 

* The most important qualities I look for are things such as a caring heart, personal responsibility, ambition, independence, common enjoyment of activities. Should I be including attire preference as one of the personality qualities I look for? How do I do this without sounding like her clothes are more important than her personality to me? Is general attire preference perhaps not as shallow as I think it is?

 

* What can I do in preparation for a date that would cause the woman to naturally see our date as worth dressing nice for?

 

You basically have two situations. If you are meeting thru OLD, put in your profile you like women who dress nicely because you like to dress nicely. For in person aquaintences, don't bother asking women out who don't dress nicely because women who like to dress nicely do all the time.

[basil67]

OK, here's a question for you: I've spent today (Sunday) in shorts, tshirt, unstyled (but clean) hair and no makeup. Is a lazy day in basic clothing acceptable to you?

 

In answer to your questions

 

* Would it come across as shallow or controlling if I expressed my own preference for dressing up for dates, and with that my preference for a women who enjoys dressing to match?

 

Depends on how you word it. "I love to get dressed up and would love a partner to share this with me" would not come across as shallow.

 

* Is there a personality trait I should be looking for, that I perhaps overlooked, that indicates or goes hand in hand with her own preference for dressing up or dressing casually?

 

I have noticed that Middle Eastern women seem to more often dress up in circumstances where I would not. Like picnics. But my Lebanese neighbours don't do this, so it's not a given.

 

* What are some circumstances that would cause a woman to want to dress up like I described above for the most causal of casual dates?

 

I can't think of any circumstance. Most women dress for the occasion.

 

* The most important qualities I look for are things such as a caring heart, personal responsibility, ambition, independence, common enjoyment of activities. Should I be including attire preference as one of the personality qualities I look for? How do I do this without sounding like her clothes are more important than her personality to me? Is general attire preference perhaps not as shallow as I think it is?

 

Easy: Don't list her dress style as an attribute you are looking for. Hint for it, but don't insist.

 

* What can I do in preparation for a date that would cause the woman to naturally see our date as worth dressing nice for?

 

There is nothing foolproof. Taking her to a really nice restaurant is a logical way to inspire dressing up. But as someone (preraph?) previously noted, some people don't dress up for anything much. That said, do you really want to drop a lot of money on a fancy restaurant for a first date which may not work out anyway?

[thecrucible]

The best way is to show a lot of positive reinforcement when she does get really dressed up so if she wants to impress you, she'll dress up a bit more. Otherwise I agree with the others that you can't really tell people how to dress. I mean I would dress up more myself but I'm more casual at the moment because a foot injury prevents me wearing heels and I don't earn enough to own a lot of really smart looking outfits.

[amkxoxo]

To be honest, what you described makes me a bit nervous for you.

 

You seem very adamant that you like your woman dressed up. But in the reality of the world, finding someone who actually wants to do that as you've described is slim to none. What if you marry a woman and she just had your baby and all she wants to wear out is sweatpants?

 

You remind me you wouldn't be happy with that.

 

I am not downing you, but I think you are being too specific on your woman. I myself love dressing up. Its fun and creative. But I dress up for work everyday so on the weekend I love wearing jeans.

 

If we were going bowling, I am not going to wear stilettos. It just doesn't fit the venue.

 

Same with movies, golfing, etc...

 

If we were going to a wedding or a really fancy restaurant, then I would definitely dress up.

 

I think you need to leave this to the woman as their choice. If they want to dress down since your going to the pub down the block, then let them. Once in a while yo could plan some nicer dates and maybe you could make it a mutual thing that you both could get dressed up for fun. I think some woman would love that. Feeling special for one night.

[clia]

The answer is to pursue women who prefer to dress on the dressier side, where that is their style. (Like the other women you noticed at the botanical garden.). I personally wear dresses, skirts, and heels often. (Even to the movies or the grocery store or a botanical garden!) There are tons of cute casual dresses available. When I wear jeans, I pair them with cute boots/shoes and a cute top. It's just my style. My sister is the opposite. She lives in jeans, sneakers, and hoodies. You are pursuing the wrong women.

[Wayne0789456]

The answer is to pursue women who prefer to dress on the dressier side, where that is their style. (Like the other women you noticed at the botanical garden.). I personally wear dresses, skirts, and heels often. (Even to the movies or the grocery store or a botanical garden!) There are tons of cute casual dresses available. When I wear jeans, I pair them with cute boots/shoes and a cute top. It's just my style. My sister is the opposite. She lives in jeans, sneakers, and hoodies. You are pursuing the wrong women.

 

Thank you! Thank you for that post. You have so hit the bullseye dead on...

 

The style I am seeking is much like yours, but the women I date have a style closer to your sisters'. I am clueless as to how to discuss this one without coming across as shallow, like the clothes are more important than her personality. I won't date the world's best dressed woman if our personalities are not a match.

 

Early phone and email conversations always include a discussion about restaurants, mostly about what kinds of food we like, and I do work in that I tend to gravitate toward more upscale casual and classier restaurants, higher end restaurants that don't quite require "formal" attire. Usually she says that sounds nice, and she does dress up informally for the first few times that we go to places like that, but it does get frustratingly old when I show up in even a higher end casual restaurant in a suit and tie, and most other patrons (men and women) are similarly dressed, while my date shows up in blue jeans. It never fails. For us to be a match in attire, she has to be unhappy in dressing up more than she wants to, or I need to make myself unhappy in dressing "too casually".

 

You used the word "style". In the early conversations, should I perhaps be asking her to describe her personal style? I've never used that word specifically, and obviously I am going about this the wrong way. Your post go me thinking that perhaps I should detach this from the restaurant discussion?????

 

BTW, I would not expect a date to dress up to goto a botanical flower garden, but I saw so many women dressed up there. Obviously, they just like to dress up period, like me. I'd love to find a woman with that personality trait, especially if I can figure that out in an early conversation.

[clia]

You are over complicating it. All you need to do is look at what she is wearing and that will tell you everything. If you are doing OLD, look at what she is wearing in the pictures she posts. This admittedly could be a little misleading since people may tend to post pictures of themselves on special occasions where they are dressed nicer, but it could tell you something. Look at what she wears on your first meet. Likewise, if you meet her in person, look at what she is wearing. A woman who enjoys dressing stylishly and dressing up is going to naturally be dressed that way -- even for a coffee date and even if she is wandering around the botanical garden. You may also have better luck with professional women who have to get dressed up for their job (at least in business casual wear), because they are more used to being dressed to the nines.

 

I guess you could ask about "personal style," but I would probably think it was kind of weird if a guy asked me that. The best way to weed this out is to meet her quickly in person for a cheap date (coffee, one drink, ice cream) and see what she chooses to wear for your first meet.

[VeveCakes]

 

You used the word "style". In the early conversations, should I perhaps be asking her to describe her personal style? I've never used that word specifically, and obviously I am going about this the wrong way. Your post go me thinking that perhaps I should detach this from the restaurant discussion?????

 

 

yeah...you arent going to be able to guage someones fashion style based off a conversation about a restaurant. I would say - the restaurant has a dress code, or say - I will be wearing a suit fyi. It's that simple. I am kind of surprised all the women you date show up in jeans? All of them? I dont think I have ever worn jeans on a first date.

[RecentChange]

Alright, I admit, I am totally unfamiliar with the online dating game.

 

But people are really showing up for dates in jeans and T shirts? No attempt to dress up at all?

 

I agree with some other posters, perhaps make some comments in your profile. I wouldn’t say I want my woman to dress like X, Y and Z – but I would mention that you enjoy dressing and looking classy when headed out on the town.

 

I am far from high maintenance, and I enjoy kicking back at the house in jeans and a tshirt….

 

But I am also a professional, so I am accustomed to wearing “business” or at least business casual 5 days a week. Which means comfortable heels I can commute in, or stylish flats. Tasteful skirts and dresses, fitted sweaters, nice button downs and tailored pants.

 

Much of my work wardrobe can be re-purposed for casual events – like a tour of a botanical garden.

 

And I will point out, it’s a botanical garden – not a monster truck rally – I would bet any of the lady’s who’s style you appreciated would step it up a notch for a date.

 

I go out on “dates” with my husband all the time. Often to causal places – but I still wear dresses in the summer, stylish jeans, boots, and nice blouses in the winter.

 

Riding Breeches. Make for a shapely leg...

 

Ha! They must, I have a habit of wearing my riding breeches and boots to run errands after I am done at the stables – it seems that smelling like a horse, and having dirt under my nails doesn’t deter guys – must be the shapely breeches!

[spiderowl]

A woman of the kind you are seeking is likely to have a profile with lots of pictures of herself in smart, fashionable clothes. She is likely to talk about clothes and fashion a lot in her profile and mention the words 'smart' and maybe 'well-dressed'. She will almost certainly say she loves dressing up and looking her best (or something of that ilk). She will probably spend a lot of money on clothes too and have a large wardrobe. I'm sure you can casually ask about these things.

[RecentChange]

I don’t think all of the above is necessarily true. I’ll agree with “smart” and “well dressed”.

 

There is a difference between being a bit put together, and being high maintenance / really into fashion etc.

 

He wasn’t describing women out in designer shoes with thousand dollar hand bags – just put together a bit. Something besides jeans, t shirts and sneakers. And honestly it doesn’t cost that much to present yourself in a bit more polished way.

 

On my jog in SF today I made a point to notice how people were dressed – Many were tourists out strolling along the embarcadero, some appeared to be locals, there were also couples out on walks…

 

What I noticed is that most were dressed the way the OP described the crowd at the botanical garden. Something besides jeans, a bit fashionable but not necessarily trendy. Most had nice footwear on, lots of cute boots on the gals, flattering coats, etc.

 

OP – WHERE in the country are you? People tend to dress up a bit more for their day to day activities in urban centers I have found.

 

San Francisco? People put more into their “look” then kick back Santa Cruz, but SF doesn’t compare to NYC, where many really address their appearance before they step out the door.

 

The small town where I came from? People would probably bother you and ask you why you were so dressed up if I wore what would be considered quite casual for a night out in the City.

[ElizabethIII]

However...

 

I was at a walk-through botanical flower garden the other day (not on a date), but noticed dozens, literally dozens, of women wearing nicer attire, and / or HEELS!!! Walking, often for a couple of hours continuously, doing one of the most casual activities that exists. Not every woman was wearing blue jeans and tennis shoes. Obviously, many women do find dressy attire (including heels) comfortable.

 

Or we've just learned how to walk in them and tolerate the pain. But believe me they hurt after you've been on them a while.

 

Who on earth would wear heels to a botanical garden unless you were absolutely sure the ground was dry and your heels wouldnt sink in the mud.

 

Do me a favor OP, buy a pair of high heels in your size and walk around on them all day, in botanical gardens and everywhere you can think of to walk. Tell me how your feet feel after the end of the day.