I agree with Jenava and Marley--you don't need to change who you are, but first impressions do count for a lot. Nothing wrong with toning things down at first till you get to know each other and figure out if he's worth investing your time in, as long as you don't change the way you dress forever. How about Whackadoodle Lite to start out with? Hm, I wonder if my DH would have asked me out on a date if I was wearing my floral pants or a faux fur leopard coat when I met him? And agree with Una--I doubt most of our DH's and SO's are as "fashion forward" as we are, so I don't think that you need to pick only guys who are interested in fashion. It's a good sign that he's noticed your outfits and thought they were interesting though!

Oh, yes, the reach on the first date. Hubs said he was really tickled when i did the reach. I told him i was tickled that he paid.

I can't remember what i wore. Just that i asked him out for lunch.

Ps...how did the boy react to your shoecase? Could that guide you?

I really like how Mary, Jenava, bj1111 and Marley put things, and echo their words.

I also really like how THE GUY noticed your shoes as they are your prized possession

Anna, mutual attraction (apart from the physical) has a lot to do with a two way sense of accessibility and ease. Wakadoodle Dressing in an extreme form, although eye catching and interesting, is not always accessible because it takes away from your natural beauty instead of showcasing it. So although I think the advice from your friend is extreme - I do think that this question is worth pondering.

The best advice I ever got was to treat dating like a job interview. I would not wear a conservative suit every day at work, but best foot forward gets you in the door and then you can ease into your real style. (be honest - nobody is their REAL unfiltered self on first or early dates). There are all sorts of things that are natural and not natural that are used to attract the opposite sex. Nothing wrong with that. Fashion is part of that business. I am not condoning pretending to be who you are not, but I've seen you in a wide range of styles and you are always lovely. Let's be honest, people (even nice people) can judge and be superficial and anything new/different can be scary or uncomfortable. Reel them in with YOU minus the distractions and THEN add the extra YOU. Feminists please don't hate me, but dating is a sport and you must use your best tactics to stay in the game.
The GUY sounds like there might be potential.

Well, I think you need to do whatever makes you happy. If you'd rather tone it down and gradually introduce a boy into your land of fun dressing, then do that. If the idea of having to dress more plainly to get a boy in the first place upsets or offends you, then don't.

I was once told - by a man - that I should nod and smile more to get a boyfriend. I was taken aback, like, oh no, really? Then I realized that a man who needed that was one I did not want. Ever.

Also, I think it's insulting to men to think they can't appreciate someone dressing a little bit differently (if they even notice the clothing at all).

Anna you have received excellent advice here and I don't think I have anything to add except that I think it is essential that you be yourself. You have a love of fashion forward style and I doubt that will change. And given it's a significant part of who you are, any prospective partner needs to know that.

I agree with MaryK, Marley, Jeneva and K (and BJ and others). I think you have been hinting that you are in the mood for a style shift for a while and your friend's comment probably hit a sensitive nerve because you have been wondering the same thing yourself. Maybe you are ready for a change and that is why you are asking the question

It would be futile to change who you are just to attract a guy or a particular guy, but if the totality of your life experience (which includes your interest in meeting someone) is moving you in the direction of change you do not need to stick to your past way of dressing just to spite yourself. I know I have never met you so take this advice as the projection and reflection of my own life's experience as you may!

I have to agree with Mary. It sounds like this may not be an issue with THE GUY right now, but I do believe it influences the dynamic in other situations or when meeting new people.

I am not advocating changing who you are for anyone, but the way people present themselves matters. For those who say that anyone who would reject someone based on their sartorial choices, how many of us have judged men in the past based on their appearance? We have even discussed cross-dressing. Some people are comfortable with that and others aren't, but I am not prepared to say that any woman who isn't okay with that is a "d*****bag", kwim?

Again, if how you dress is an integral part of who you are, then don't change for anyone. But sometimes letting one item (like the shoes!) do the talking in an outfit is more approachable overall than an outfit full of statement pieces. And it is worth considering if you use your fashion choices as a kind of armour or shield between you and the world. Most of us do to some extent, but when that makes it harder for people to see or approach the real you behind your clothes, then it might be worth reconsidering.

I am a card-carrying, formerly bra-burning (sorta) feminist, and I agree with MaryK.

This may not be the case with The Guy, but on the future first coupla dates, I wouldn't go with your most wackadoodle outfits.

Your most fashion-forward outfits are creative and interesting, but they may obscure the real you. I've met you in real life, and you are absolutely gorgeous. Coupled with your sense of humor, energy and your sultry voice, who could resist once they meet and "see" the real you!

That said, I sense that your style persona is evolving to a more subdued persona on it own, right?

Echo! That's so true! We have TOTALLY judged blokes for the way they present themselves, and still do. They are totally within their right to judge us in the same way.

As for changing who you are for a loved one or potential love prospect - I don't think there is anything wrong with changing who you are within reason. And in the same breath I will admit that these parameters are hard to set (how much do you change, and how much do you stay who you are). But often people change for the better - and that is my point.

ETA: The second point about changing who you are is a general statement, Anna. And not one specifically targeted at you.

I feel I should reclarify. I always tone down how I dress for first dates. I would never wear my harem jeans on a first date. I know they are very Manrepelling.
I also feel that I dress appropriately for the occasion. For example see my opera outfits and recent conference outfit.
Still processing all your responses.

OK, coming back with some more levelheaded thoughts after my initial knee-jerk reaction.

I don't think it's necessarily a bad thing to want to change for a person with whom you are in a relationship. As others have said here, it's often for the better, and it's natural to want to make yourself more pleasing to someone you love. I would hope that the other party would also try to do the same for you, since it's always a two-way street. However, I do have a bit of a problem with changing something fundamental about oneself for the purpose of attracting a mate. It's kind of just like starting on the wrong foot entirely, you know? But I haven't looked for a date for many years, and I met J. in college (although we broke up for a few years afterwards) where the rules are kind of different. I never really dated in the real world. Which is to say, I may have a completely unrealistic outlook on the whole dating thing.

Also, toning down how you dress is one thing, but completely changing your style is another thing altogether. For one thing, if you just tone down but keep it the same general style, it's a lot easier to ramp it back up once you know the person better. I do get wanting to appear more approachable or low-maintenance, although by and large I think guys don't realize how much work is involved in getting that "natural, low-maintenance" look they all seem to love.

J's style is very different from mine, he is quite a conservative and preppy dresser. I tease him about his closet full of blue and white shirts. (Although recently he bought a lavender one! Baby steps... ) I happen to know that his taste in women's clothes is pretty simple and classic, but he also loves how I dress (although he doesn't always get it) and acknowledges that the simple and classic look would be totally out of place on me.

If the goal is to meet guys, more conventional style would probably help achieve the objective. If the goal is to meet someone who might be a life partner, or a deep and meaningful relationship, making a drastic change to something that is really important to you feels like the wrong approach to me (even though there is no right or wrong answer here). It feels off.

Would you change your style permanently? Or just early on and then go back to your true self?

Here's a different way to consider this multifaceted issue. How would you feel if you were in a serious relationship with someone and everything was perfect until he asked you to tone down your style and wear something more in line with what he finds attractive? Would you compromise to meet your partner halfway and make a personal sacrifice because he asked? Or would you find it offensive of him to even ask?

Finally, a short anecdote that offers yet a different perspective. My husband does not really care about fashion. Even with a newly slim and trim body, he just doesn't care, and is wearing old things that fit from years gone by (meanwhile I am DYING to buy him fab new things). I pushed early on for him to wear things that were more to my liking. He told me that he did not appreciate me trying to change him and asked me to back off, which I did, because I love him, and in the big scheme of things that are important in a life partner, his choice of jeans or the pattern on his shirt just didn't make the cut. By the same token, he knows I love clothes and fashion, and he supports and encourages it.

This is an interesting, thought-provoking discussion, Anna. Good luck sorting through what makes sense for you.

Thanks for this thoughtful post, Anna - I've learned a lot too!

Hi Anna, I think I am with Mary K. Your friend is obviously a good one because it is hard to say something like that and unlikely to be malicious. She knows you, him, the guys you fancy, your real self etc presumably, and she said that to you. I don't see it as a directive to subliminate your true-self which has wide ranging ramifications for your personality and self expression if you hook up with The Guy. He obviously finds you interesting but In my experience a new man's radar is out for, extravagance, self indulgence, eccentricities etc.. Without being that conscious of it. He could see you as outrageously confident and a bit nuts- shoe wall, would be a bit scary for a pretty straight guy.

NOW- in the looks stakes you are naturally gorgeous. Haven't seen u with your hair up but loosely up would look fab. I think it is easy to let lots of fab clothes actually detract from and hide your natural beauty. You looked great in the hicking shot and you are obviously an outdoor girl as well.
There are a multitude of conversations within a feminist paradigm here- on all sides. The female gaze is the cameras gaze. The gaze is most likely male. YLF has a strong effect in empowering the female gaze!!!! Yay
Just reverse the positions and see what assumptions you might make about him according to what he wears. Are they valid? Are they inevitable?
Just some thoughts.

I don't think you should change the way you dress!

That said, I agree with others in that this may be a case of situationally appropriate, or something like a job interview, even though it really shouldn't be like that all.

All of the date night outfits I've seen you post have been FAB, and you're on the right track, as far as I'm concerned. Just beautiful and you have nothing to worry about on this front!

Not sure if this helps, but I like to cook - and sometimes I cook some weird things. Things other people might think were totally bonkers. That said, I am not going to take grilled octopus with blueberry compote to a dinner party when meeting new friends or family members of significant other. I'll 'tone it down' a wee bit so that everyone can enjoy - and even if my 'toned down' is still a little out there at times, it's still a good conversation piece.

I also like what others have said about being accessible, as well as showing off *you* so that your fabulous style doesn't obscure how beautiful you are. It's just like what they all say in terms of interview advice - allow yourself to shine so that the first thing people see is you, and not necessarily the outfit you put together, if that makes sense.

No need to change your style at all - but it is possible that your amazing style might be a tad bit intimidating at first. Like me showing up with octopus and blueberries - when I could have come up with something that everyone knows and likes (ie. macaroni and cheese) but with a totally new and fab twist. Maybe I make my mac & cheese with sundried tomatoes, pancetta bacon bits, shredded spinach and four kinds of gourmet cheese.

Come to think of it - this reminds me of Angie's outfit blog post today - a pencil skirt and blouse, and yet her pencil skirt and blouse are amazing. Anyone meeting her would immediately know there was something different and very special about her.

I see you the same way. Your "toned down" outfits are so spectacularly fab that a person couldn't fail to notice that you are someone special.

I guess this is my very long-winded way of saying that even if you did change up your date outfits a wee bit, they are still going to be *amazing*. It's kind of tough to hide your light, even if you try to.

You could wear a potato sack and look glamorous. This is just part of who you are.

I can't make ordinary macaroni and cheese - I'm always going to sneak in some asiago (or feta even), some sun-dried tomatoes or what have you.

You're the same way. A pair of jeans and a button-down shirt are going to look extra-fab on you, because you have incredible style and there isn't going to be any "going back" if that makes sense.

So, if you decided to keep on with the so-called "toned down" outfits for date-nights, never fear - your 'toned down' is still going to be kock-your-socks-off fabulous. You won't lose anything - because this incredible style that you have cannot be hidden, no matter how hard you try. You're not hiding yourself or "dialing back" in any way - you're just showing up as your fabulous self in a slightly more accessible way (at first )

Hope this wasn't too long, and more importantly - that it made some kind of sense.

I agree with ironkurtin:

Well, I think you need to do whatever makes you happy. If you'd rather tone it down and gradually introduce a boy into your land of fun dressing, then do that. If the idea of having to dress more plainly to get a boy in the first place upsets or offends you, then don't.

I'm trying to walk this line at the moment socially. It has been hard & I've wasted a lot of energy on it - I'm coming to the conclusion that if people don't like my "first impression" maybe it is for the best

First of all Anna, know that you have amazing style and are a beautiful woman, inside and out.

My paternal Grandmother was an incredible woman but had a very strong personality. And she wasn't like the other women of her generation in terms of taking a back seat to men. She wore pants and liked to work with her hands. Men were intimidated by her. But she found a wonderful man and they were married for 72 years. He adored her strong spirit.

I remember her telling me one time when talking about men ..."you don't have to show them the whole deck of cards at once, you know". Apparently when she was dating my grandfather she revealed her true self a little bit at a time and by the time my grandfather knew everything about her, he was already completely in love.

It seems like you care about The Guy and he obviously is fond of you. I mean c'mon, he mentioned you have interesting shoes - that is a great sign IMHO! Just maybe give him small doses of your style until he gets to know your personality more. A strong style can make the person invisible.

Awesome question, Anna -- and lots of great answers, ideas, thoughts from everyone. You probably don't need anymore, but I feel for you and just maybe I'll have something to add. . . Do you think your friend was saying that in your best interests? or is she possibly saying how she feels your style isn't conventional enough?

I'm also not great at 'how' I say things, so I'll apologize in advance for anything that sounds blunt! But being married for 30+ years to a guy with four brothers, raising two boys, and now the only female in the house with my guys, has me only able to say that guys are inherently weird and different than girls.

A guy that 'gets' style is the exception (i.e. Angie's Greg). I think the majority of men are pretty ambivalent about it. Yet every person/man will still have things he likes/dislikes (i.e. colours, heel heights, makeup, hair length, etc.) and you can't predict someone's preferences. I want you to be able to just be yourself and meet a great guy that loves you just the way you are! And whether that includes whackadoodle style or not!

I hate to think of anyone being disingenuous to meet a man or maintain a relationship. But putting more fashion forward/extreme style on the back burner while you get to know someone seems perfectly legit to me. If I were in the early stages of getting to know someone I was interested in, I'd not only be agonizing over every outfit, I'd also be more likely to brush teeth and hair more, freshen makeup for him, do my nails, drop a pound or two, use extra deodorant, you get the idea. I consider this all part of trying to put my best foot forward (like Jjsloane's interview idea), and not disingenuous.

My head swirls with all sorts of motherly advice (and brings to mind conversations with my own daughter about some things she'd get a bit 'militant' about - using as a sort of litmus test for dates)

. . . and VC is right about even 'toned down' you will exude an elegance

Echo, I am wondering if your "I am not
prepared to say that any woman who isn't okay with that is a
"d*****bag, kwim?" is aimed at my earlier comment that any man who would ditch a woman because of her clothes is a d-bag. If it is, I think the application of the d-word is getting kinda muddied, if possible.

To clarify, my position is one of tolerance for other people's harmless foibles, and when other people aren't tolerant or get judgey I consider that pretty d-worthy. Especially for something like appearance. Heaven knows we've all dated men who couldn't dress if their life depended on it (see stories above in this thread). My own beautiful man wore pleated pants and the worst possible grown-out Abba haircut to our first date. Luckily I saw past all this to his cute smile and it's been over twenty years. He certainly saw past my manly cropped hair and thigh-high boots! Isn't Anna entitled to the same acceptance from whoever she dates?

Yes, men can be dumb. Yes, they may see Anna's feathers first and then her face. But... why is that something Anna needs to change? The thought that she is scaring off men by being an individual seems so wrong to me. The thought that how she dresses somehow obscures the "real her" also seems really wrong to me. If she hasn't found a guy, I don't think it's her clothing. I think it's because karma hasn't hit yet.

It's one thing to meet someone, realize s/he loves X look, and then change for them. It's another to change yourself blindly because you think someone else wants it (without knowing it's true) and that there's something wrong with how you are. Yes, people judge by appearances. But you can make yourself nuts trying to figure out what people think.

I think really the only thing you can really do is be secure in yourself and, by extension, be happy and confident in what you wear. Whether that's a LBD or silver lame. And if that turns someone off, well, then IMO they weren't worth the time.

I think perhaps many of us will just agree to disagree. I'll just say that many people have changed how they present themselves in certain situations in order to make themselves appear more approachable. That is something that some people are comfortable doing and that some people are not.

I think a job interview and a date are not comparable. You dress for an interview in the hopes that you will get a job. To get the job, you adapt to the company's tastes and necessities. Ideally, you shouldn't need to change yourself in order to get a mate. Wearing blue because you know that's his favorite color? Sure, there is nothing wrong with that. Not wearing chunky necklaces because he doesn't seem to appreciate them? Ok. But starting to dress like Suz or Lyn* (I consider both opposed to you in terms of style) just because he MIGHT like it better (you can't even be sure), I don't think that's ok.

Also, if it is true what some have pointed out that you dress yourself in order to hide your body and personality behind your clothes, maybe you should consider changing that. Not for a guy though, just for yourself. You will need good self-esteem to get a guy (and anything in this life, really). And you do want people to see you.

For the record, I once dated a guy (for some months) who dressed very conservatively. He was 27 and never wore jeans. Not even during weekends. He was conservative in other aspects as well, of course. I'm not an edgy dresser, but I do have my quirks. He was shocked when I bought a pair of red converse sneakers. He was THAT conservative. However, he still liked me and we stopped seeing each other for other reasons. He never commented on my style in a wrong way. I have to admit I was put off by the vibe of his style and it was one of the many reasons I wasn't sure about him. His outfits told me he was boring, serious (in a 'not fun' way) and traditional. He turned out to really be all those things, which were not necessarily bad, but definitely not attractive to me.

Just wanted to say I second what MaryK said 100%.

Just wanted to support what Mary and others said. And also wish you all the best, because you deserve it

Anna, the guy sounds as if he enjoys your look. Perhaps he even looks forward to seeing what "interesting thing" you're going to wear next. So why deny him that pleasure?

Seriously, he's already noticed that you're an interesting dresser and complimented you on it. If you change your look now and try to start dressing more classic and conservative He. Will. NOTICE.

I have a lot of male friends and they tell me stuff about guys and dating. Stuff that magazines and female friends won't. Specifically, that they notice when women try to make themselves more "acceptable" and "appealing" to them. Like when the woman who lives on takeaways starts always cooking for him. Or when the woman addicted to reality shows starts watching more high-brow things. Or when the woman with quirky, personal style loses her nerve and becomes a bland, catalogue model clone.

My guy friends tell me that this kind of behaviour sends up a massive red flag that the woman is insecure and desperate to please. It's like screaming, "look how sensible I am! See what good girlfriend/future wife material I am!" And it puts them off.

When a woman tries to bury everything that makes her interesting and unique, why should a man stay with her? What does she have to offer him? The media would have you believe that sex appeal and looking perfect is all you need to keep a man. In real life, there's so much more to it than that.

Again, I'm skipping thru all the comments to say nononononono, please don't change the way you dress for some guy...whether an imaginary guy out there, or real person. I'll say it one more time. Please, no.

I think with this particular guy, you are way past the first impression stage. It's going to happen or it won't, but no need to go changing your style. It sounds to me like he appreciates your look - he said so, why second guess it? Who can say whether you will eventually get together, but don't go changing for this one.
I know you are always appropriate and tone it down for first dates. I do think you have some conventionally beautiful, flattering outfits that would also make great first date picks (such as the outfit you wore for your dad once). Only you can decide if those looks feel enough like *you* to put your best foot forward in.
I sometimes wonder if you over think your outfits for dates/singles events. There's some anxiety there that sometimes manifests as new purchases or wants, right? Frankly, I think you have way more invested in being fashion-forward etc than the "average guy" is going to appreciate. There's nothing wrong with that, per se, there just may be a slight disconnect between what makes you feel super attractive and what guys are noticing on first meeting. They look at your hair, your smile, etc, not your labels. It might help to separate the anxiety/pressure around dating from the dressing.
Finally, you are not just pretty, you are a stunner. Fit, blonde, hot!

I don't think one needs to change how they dress for another person, but I have picked up on some of the same comments from you that other's have pointed out. The comment Maryk mentioned about being "interesting" because you're not "pretty" really stuck with me. There was also another comment or two that bordered on putting down people who dress in a boring way that caused me to wonder how much judgement you place on the way other people dress. All this balled together has made me quietly wonder if there is some deeper issue that urges you to dress the way you do. I don't think you need to change you how dress just to please a man, but I do think you need to dig deep and make sure that you dress the way you do due to positive, self affirming, happy reasons.

If your clothes are some sort of armor you've put on, or some sort of message you're sending, you may need to look at the unintended results of that armor or message and decide if it fits with the other things you want in your life.

Wow! I saw this thread last night when I was too tired to read all the responses, much less form any kind of coherent thoughts, so this has been an interesting read over my morning coffee.

Anna, you've received lots of (somewhat conflicting) advice, and I see merit in every one of the viewpoints expressed here. Once again, I'm struck by how thoughtful and intelligent this community is.

That said, I think the bottom line here is -- and forgive the platitude -- being true to yourself. Your style *has* been softening lately, and you have been pondering a shift. Even though I don't necessarily agree with your friend's comments, it would seem she touched on something you've already been thinking about.

I think we can sometimes use clothing as armor or distraction without even realizing it. But I think if you are considering "softening" your style, it should be because it's for YOU and not anyone else. It should be because it makes you feel beautiful or powerful or sexy or confident -- whatever it is you want to feel to be the best version of you.

I am totally confident that even if you alter your style, you will still continue to rock a truly unique look that stands out in a crowd and that others admire.