A
female
age
36-40,
anonymous
writes:I met this guy a few weeks ago and we have been on quite a few dates. The first time we met I was wearing a skirt with a slip underneath. As he told me then and keeps telling me since, that he loves me wearing such clothes, I have always dressed similarly like this for him. My issue is: does he like me or just because what I'm wearing? We really get on well and I don't mind dressing this way. I could once turn up in jeans etc. to test the waters, but I am worried that I won't like his reaction. What do you guys think? Reply to this Question
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female
reader, So_Very_Confused  +, writes (21 July 2014):
 By all means test the waters....
My husband has distinct "rules" about dressing
jeans or leggings are fine
pants are a no-no for him.
women are to be in feminine attire at all times.
he likes me in skirts or dresses... body hugging...
we had to come up with a rule:
he has say over what I wear when we have date night...other than that he gets no input.
at home i live in leggings and he's learned to cope.
He will comment on stuff he does not like when I get home from work... and I always ask what he wants me to wear when we go out together... he's relaxed over the last few years or so about it...
NEVER dress 100% of the time to please a man...
A
male
reader, Sageoldguy1465 +, writes (20 July 2014):
 I think you SHOULD go ahead and wear something outside the realm that you know is his schtick. THEN, you will find out if he is in to your clothes, or YOU!!!!
Good luck....
P.S. I always try to convince girls that I like them WITHOUT clothes(!!!).... since that gives me an opportunity to REALLY "see" THEM!!!!
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A
female
reader, CindyCares  +, writes (20 July 2014):
 Yes, you should test the waters. It's normal if he has fashion preferences and he likes a certain outfit more than others, but if he only likes you when you are wearing one style, then he is not into you but into the " persona " you represent, into a generic ideal of a woman and not into the real you- who is probably multifaceted and can be uberfeminine, but also sporty, or sexy , or no frills etc.etc., according to moods and circumstances.
Plus , I'd think it would be very high mantenance ( and boring for you ) always have to show up in your full 50's regalia ( a slip ?? Who wears slips today ??, unless it's some tongue-in-cheek Victoria's Secret 's number JUST for the bedroom ? ) Wouldn't you feel eventually as if you are Lucy Ricardo ?...
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A
female
reader, oldbag +, writes (20 July 2014):
 I should hope he would.
Yea men like feminine women but jeans and a top can be just as appealing. Could be he's a 'leg' man, but skinny jeans or even shorts show off legs too.
Just wear what your comfortable in, dress for the occasion.
So as long as you smell gorgeous and your hair shines you could probably wear a bin liner and he would approve
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A
female
reader, anonymous, writes (20 July 2014): I actually think you SHOULD test the waters and turn up for a date looking feminine but not wearing the usual style of outfit that you have been wearing - like Abella suggests, some nicely cut jeans or tailored trousers with a pretty top.
If it goes down like a lead balloon then you'll know that the guy's more into your "look" rather than you and you can decided whether he's proper relationship material. My guess is that he'll probably like you just as much as he did in the skirt.
It's fine to dress in a way that you know appeals to your boyfriends tastes but it's not okay to feel that you HAVE to dress a certain way to please him or keep his interest. This is someething that I'd need to find out during the dating period so I say go for it!
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A
reader, anonymous, writes (20 July 2014): Plan a date where more masculine clothes are necessary because they're practical, like paint balling then a meal, so you don't have time to change before the meal and you'll see if he likes you as you are or not :)
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A
female
reader, Abella +, writes (20 July 2014):
 There is no doubt that he loved the femininity of what you are wearing. And the fact that you demonstrated your femininity stirred something within.
I have always loved seeing guys in luscious corduroy pants. No I don't know why it stirs me, but some wide corduroy gunmetal grey pants look delicious to me.
But what you were wearing was just part of who you are. If you turning up in pants turns him off then he's not the man for you. However I think you are more than just your clothing to this guy.
Test the waters if you want with one of your feminine tops and a nicely cut pair of jeans or pants, whichever you prefer.
I suspect he will still like you whatever you are wearing.
Believe in yourself. There is so much more to discover about you than just what you are wearing.
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