What to wear [UPDATED: is it okay to see him again?]

[mortensorchid]

This weekend I have a date with someone (at least I am 90% sure of it at this point). I have a dilemma with this ...

 

Most days you will find me on down time dressed very tomboy. As it's summer I will be found wearing shorts, a T shirt, athletic shoes / flip flops, with a hoodie tied around my waist. I am not a very girly girl type, I usually don't wear make up if I don't have to. But I also like to change my appearance a lot, I experiment with many different things to transform myself.

 

Will this detour from attracting men? If they see me as being "one of the guys" or if they see me as the one who doesn't make themselves look as girly as possible, will they put me in another category? And if you were going out with this person, what would you wear?

[CautiouslyOptimistic]

I think your normal casual attire is fine, but not for a date. Dress a bit more feminine.

[thefooloftheyear]

It would "detour" me.....

 

I'm not a woman, but if I was and was angling for a connection, Id make sure that all my ASSets are looking their best...Save the casuals for when you have been dating for a while and want to sleep in on Sunday morning and watch the NFL games..

 

But that's me....Some other guys would probably be cool with it..

 

TFY

[RecentChange]

Where is the date? What time of day?

 

I am a Tom boy at heart, but I can still throw on a dress or a skirt.

 

Even some nice close fitting jeans, cute flats and a feminine shirt should work for many circumstances.

 

Again, depends on location and time - but I could imagine wearing a "shirt dress" a fun loud belt and some flats to a first date.

 

 

http://fashiongum.com/wp-content/uploads/2015/04/Shirt-Dresses-Street-Style-2.jpg

 

 

https://s-media-cache-ak0.pinimg.com/736x/13/f2/8b/13f28be08e9970bf5c0ce73984fce7b0.jpg

[divegrl]

I would go with a sundress. Or maybe a cami and skirt?

 

As for makeup I'm very natural as well. A tinted moisturizer, mascara, eye liner and a lip gloss should be fine.

 

I'm excited for you..... I hope it goes well!!

[Ruby Slippers]

I almost always wear a cute dress for a first date. You can get cute and very comfy throw-on dresses pretty cheap. Jazz it up a little with sparkly stuff, makeup, cute sandals or heels. Showing up in a feminine disposition brings out a man's manliness, which I adore

[No_Go]

It may deter some but in the end of the day - you're looking for guys that like your type, so they'll stick with you, so no point to make false first impression.

 

Is there anything more feminine that you enjoy wearing? E.g. instead of T-shirt some form fitted top, instead of shorts - skinny jeans, instead of flip flops - sandals (heels/wedge even if low would look more feminine)?

 

Or just go on active dates - like sports, hikes etc, where the tomboy clothing is not only accepted, but also expected:)

 

This weekend I have a date with someone (at least I am 90% sure of it at this point). I have a dilemma with this ...

 

Most days you will find me on down time dressed very tomboy. As it's summer I will be found wearing shorts, a T shirt, athletic shoes / flip flops, with a hoodie tied around my waist. I am not a very girly girl type, I usually don't wear make up if I don't have to. But I also like to change my appearance a lot, I experiment with many different things to transform myself.

 

Will this detour from attracting men? If they see me as being "one of the guys" or if they see me as the one who doesn't make themselves look as girly as possible, will they put me in another category? And if you were going out with this person, what would you wear?

[No_Go]

I feel like if she's not wearing make up regularly eyeliner will be overkill... But mascara and gloss are easy even for someone that never touched make up before

 

Foundation / base I'd use only if she knows how to do it. Even low coverage tinted moisturizer can look very weird on someone applying it as face paint all over...

 

I would go with a sundress. Or maybe a cami and skirt?

 

As for makeup I'm very natural as well. A tinted moisturizer, mascara, eye liner and a lip gloss should be fine.

 

I'm excited for you..... I hope it goes well!!

[preraph]

Tomboy gear does little or nothing for most men and it really should only be worn when you're doing something active like hiking or fishing or home alone. I sympathize. I was an extreme tomboy growing up in the country and had a dirt bike and horses and helped my dad in the garage. Thankfully, my mom sewed clothes for me and had me wear them or I'd have looked a mess. Then I started liking the cool sixties clothes and got into dressing in that way. But then I became a hippie and dressed way down again.

 

Still, I had a thing for the luxury fabrics and vintage clothing so I didn't stay in slacker clothes long, but next was wearing all black all the time. And all I can tell you is that I did a lot better once I was dressing like a woman. In my middle age, I got girly for the first time and liked ruffles and chiffon, and for an old hag, I got some interest I think just because of the pretty clothes, though it was fleeting due to my age.

 

I mean, you can still make plenty of time for casual clothes, but don't ever wear them on a date unless the date is sporting and active.

[SammySammy]

Slightly overdressed for the occasion. That general rule seems to always work for men and women.

 

Slightly ... overdressed. Don't overdo it.

 

I'm attracted to girly girls, so I like anything feminine. But, I appreciate a woman who can go without makeup. That shows confidence and a level of confort with herself that's also very attractive.

[coolheadal]

This weekend I have a date with someone (at least I am 90% sure of it at this point). I have a dilemma with this ...

 

Most days you will find me on down time dressed very tomboy. As it's summer I will be found wearing shorts, a T shirt, athletic shoes / flip flops, with a hoodie tied around my waist. I am not a very girly girl type, I usually don't wear make up if I don't have to. But I also like to change my appearance a lot, I experiment with many different things to transform myself.

 

Will this detour from attracting men? If they see me as being "one of the guys" or if they see me as the one who doesn't make themselves look as girly as possible, will they put me in another category? And if you were going out with this person, what would you wear?

 

My dear why are you changing who you are outside. Go as you are.. Unless your going to a formal dinner then slip on black dress some heels. Shoot I always wear Sportswear from Nike full outfit.. I have my 3 colors Black, Grey and Blue with matching Nike sneakers. If it rains or it's a cold day then Nike full body sweat suit and Nike Blue Hoodie.. People should be who they are outside as well never change if you don't want to change. These guys either drop and run or stay and play! Same goes for women too with the guy they want.

Edited July 7, 2017 by coolheadal

[d0nnivain]

One of the best wardrobe tips I ever read which I now swear by is to wear "touchable" fabrics on dates. Whatever you pick make sure it's of a material that your date would want to feel next to his skin: a silk blouse, a cashmere sweater.

 

 

That's a little tougher in summer but go with cotton. If as a TomBoy, the idea of a skirt seems foreign to you, consider a skort: it looks like a skirt (so feminine) but it's really shorts. Pair that with a soft, cotton, feminine tee in a "girly" color. By that I mean, no sleeves that hang halfway to your elbow & are blousy. Something with cap sleeves that is more form fitting / body skimming but not skin tight. Put on a pair of sparkly earrings, not necessarily gaudy rhinestone but something that glints in the light; a simply pair of pearl studs or small gold hoops. Consider very basic makeup: eyeliner, mascara & a true to shade lip gloss, that matches your lips but adds a bit of shimmer without a lot of color or heaviness.

[kendahke]

This weekend I have a date with someone (at least I am 90% sure of it at this point). I have a dilemma with this ...

 

Most days you will find me on down time dressed very tomboy. As it's summer I will be found wearing shorts, a T shirt, athletic shoes / flip flops, with a hoodie tied around my waist. I am not a very girly girl type, I usually don't wear make up if I don't have to. But I also like to change my appearance a lot, I experiment with many different things to transform myself.

 

Will this detour from attracting men? If they see me as being "one of the guys" or if they see me as the one who doesn't make themselves look as girly as possible, will they put me in another category? And if you were going out with this person, what would you wear?

 

It depends upon what is attractive to the guy in question.

 

What type does he say he likes? You do run the risk of turning the guy off if your roll in looking like a dude, so you should have some clue as to what they like before meeting them. I'd ask him what he likes to see women wear. If it's too much for you, then you know right away it's going to be a short night, so wear what you normally wear and have 2nd tier plans for the evening.

 

To me, putting some effort into one's appearance when meeting me for the first time says that they value not only themselves, but they are thinking about me and want to make a good first impression, for which you don't get a second chance. I put in some effort to look nice and feminine when I go out on dates... there are plenty of times the other 364 days to dress as I normally do.

 

I vote for a loose blouse/top and a flowy maxi skirt, flat sandals, minimal make up and gorgeous hair.

[smackie9]

maxi dress and sandals....................put on some lip colour.

[Dis]

Ooooooooo!!!! Yay!

 

Its great to be yourself but since you said you like the 'transform' yourself and it is the first date...go for it and dress like a bombshell!

 

I always wear a cocktail dress..usually a Bodycon/bandage dress. Its not too formal but its dressy enough to do the trick

 

Here are some examples: Bodycon Dresses: Bandage & Fitted Dresses | bebe

 

I usually go with black because...little black dress!

 

Shoes...how are you with heels? Nothing says feminine like a nice pair of heels

 

These are pretty fierce: https://shop.guess.com/en/catalog/view/shoes/women/dress/keiry-platform-sandals/gwkeiry3?color=blkll

 

They wont be too difficult to walk in either because of the platform. Just put all your weight on the ball of your feet...not your heel

 

Makeup...I never like to over do it with lets say, a smokey eye. Its just too much. IME, guys get turned off be heavy makeup. A neutral eye with a darker lip (but not too dark) would be awesome!

 

Acessories. Less is more. And it depends on the cut of your dress. If you have a low cut dress...go with a necklace and some studs

 

One final tip....dont show too much boobs. You want to show a little but not like...heyyyy look at my chest all night!

 

One final, final tip....always wear a push up bra

 

Thats just what I would wear though. Do what feel comfortable for you and most importantly....have fun!!!!

[tetrahedral]

Ooooooooo!!!! Yay!

 

Its great to be yourself but since you said you like the 'transform' yourself and it is the first date...go for it and dress like a bombshell!

 

I always wear a cocktail dress..usually a Bodycon/bandage dress. Its not too formal but its dressy enough to do the trick

 

Here are some examples: Bodycon Dresses: Bandage & Fitted Dresses | bebe

 

I usually go with black because...little black dress!

 

Shoes...how are you with heels? Nothing says feminine like a nice pair of heels

 

These are pretty fierce: https://shop.guess.com/en/catalog/view/shoes/women/dress/keiry-platform-sandals/gwkeiry3?color=blkll

 

They wont be too difficult to walk in either because of the platform. Just put all your weight on the ball of your feet...not your heel

 

Makeup...I never like to over do it with lets say, a smokey eye. Its just too much. IME, guys get turned off be heavy makeup. A neutral eye with a darker lip (but not too dark) would be awesome!

 

Acessories. Less is more. And it depends on the cut of your dress. If you have a low cut dress...go with a necklace and some studs

 

One final tip....dont show too much boobs. You want to show a little but not like...heyyyy look at my chest all night!

 

One final, final tip....always wear a push up bra

 

Thats just what I would wear though. Do what feel comfortable for you and most importantly....have fun!!!!

 

This is useful general advice, but for the OP it might be too aggressively feminine.

 

OP, if you wear a dress and basic makeup (eyeliner and lipstick) you'll be fine. The goal is to not be underdressed, and that'll get you there.

 

Besides, any detail beyond that is lost on 90% of guys.

[No_Go]

I personally will go to the style that you describe in a heartbeat because it is very similar to my daily clothing (except I wear fit & flare knee length dresses or if work requires - sheath style although I still prefer fit & flare)... So just putting heels on will not make me look like a different person. For her it will make her look super different than what she looks like on day to day basis - so the guy will fall for an image that she won't maintain most likely...

 

I feel like she should dress up but still keep looking like the same person.

 

I think bold lipstick and push up bras should not be used for dating but that is for logistic purposes (I mean touching padding or smearing bright lipstick is... well not what most guys like). I think make up if any should be focused on the eyes and the underwear should be something that she feels ok getting undressed to (like no spanx and too much padding - even considering that sex is off the table)

 

Ooooooooo!!!! Yay!

 

Its great to be yourself but since you said you like the 'transform' yourself and it is the first date...go for it and dress like a bombshell!

 

I always wear a cocktail dress..usually a Bodycon/bandage dress. Its not too formal but its dressy enough to do the trick

 

Here are some examples: Bodycon Dresses: Bandage & Fitted Dresses | bebe

 

I usually go with black because...little black dress!

 

Shoes...how are you with heels? Nothing says feminine like a nice pair of heels

 

These are pretty fierce: https://shop.guess.com/en/catalog/view/shoes/women/dress/keiry-platform-sandals/gwkeiry3?color=blkll

 

They wont be too difficult to walk in either because of the platform. Just put all your weight on the ball of your feet...not your heel

 

Makeup...I never like to over do it with lets say, a smokey eye. Its just too much. IME, guys get turned off be heavy makeup. A neutral eye with a darker lip (but not too dark) would be awesome!

 

Acessories. Less is more. And it depends on the cut of your dress. If you have a low cut dress...go with a necklace and some studs

 

One final tip....dont show too much boobs. You want to show a little but not like...heyyyy look at my chest all night!

 

One final, final tip....always wear a push up bra

 

Thats just what I would wear though. Do what feel comfortable for you and most importantly....have fun!!!!

[kendahke]

Ooooooooo!!!! Yay!

 

Its great to be yourself but since you said you like the 'transform' yourself and it is the first date...go for it and dress like a bombshell!

 

I always wear a cocktail dress..usually a Bodycon/bandage dress. Its not too formal but its dressy enough to do the trick

 

Here are some examples: Bodycon Dresses: Bandage & Fitted Dresses | bebe

 

I usually go with black because...little black dress!

 

Shoes...how are you with heels? Nothing says feminine like a nice pair of heels

 

These are pretty fierce: https://shop.guess.com/en/catalog/view/shoes/women/dress/keiry-platform-sandals/gwkeiry3?color=blkll

 

They wont be too difficult to walk in either because of the platform. Just put all your weight on the ball of your feet...not your heel

 

Makeup...I never like to over do it with lets say, a smokey eye. Its just too much. IME, guys get turned off be heavy makeup. A neutral eye with a darker lip (but not too dark) would be awesome!

 

Acessories. Less is more. And it depends on the cut of your dress. If you have a low cut dress...go with a necklace and some studs

 

One final tip....dont show too much boobs. You want to show a little but not like...heyyyy look at my chest all night!

 

One final, final tip....always wear a push up bra

 

Thats just what I would wear though. Do what feel comfortable for you and most importantly....have fun!!!!

 

These would be cool after she's gotten to know him and he's used to her style and she wants to surprise him, but not on a first meeting because this isn't who she is. At. All.

[Dis]

This is useful general advice, but for the OP it might be too aggressively feminine.

 

OP, if you wear a dress and basic makeup (eyeliner and lipstick) you'll be fine. The goal is to not be underdressed, and that'll get you there.

 

Besides, any detail beyond that is lost on 90% of guys.

 

I personally will go to the style that you describe in a heartbeat because it is very similar to my daily clothing (except I wear fit & flare knee length dresses or if work requires - sheath style although I still prefer fit & flare)... So just putting heels on will not make me look like a different person. For her it will make her look super different than what she looks like on day to day basis - so the guy will fall for an image that she won't maintain most likely...

 

I feel like she should dress up but still keep looking like the same person.

 

I think bold lipstick and push up bras should not be used for dating but that is for logistic purposes (I mean touching padding or smearing bright lipstick is... well not what most guys like). I think make up if any should be focused on the eyes and the underwear should be something that she feels ok getting undressed to (like no spanx and too much padding - even considering that sex is off the table)

 

These would be cool after she's gotten to know him and he's used to her style and she wants to surprise him, but not on a first meeting because this isn't who she is. At. All.

 

The OP should do what I suggested in my last sentence, which was do what feels comfortable for her

 

Since she said she likes to transform herself...I figured why not dress to the 9's?

 

Push upbras only have padding on the underside of the bra...hence the push up effect and if you get a well made bra like VS...it would feel fine to the guy if it were to get to that point

 

I love the flair fit skirts and dresses too No Go!

 

Detail is not lost on men. Look at famous entertainment figures, Scarlett Johanson, Angelina Jolie and the ever so useless Kim Kardasian They put themselves together flawlessly and the result.... *man drops jaw* I love seeing that look on my dates face but if the OP doesnt want to go that route...thats totally fine

[K.K.]

You could wear skinny jeans with sexy little shoes. Not flats. Maybe platforms so they are easier to walk on. And a sexy blouse! They have these sexy little blouses everywhere with cut out shoulders. But don't overdo it. A ladylike blouse not really too low cut but somewhat low. The blouse will balance out the jeans so it doesn't look too tomboy. Something flowy that hits at just the right length to make your butt look good.

 

I'm a tomboy as well, really. Jeans and t shirts mostly. But my t-shirts are really sexy and fit right. I don't have big boobs so I can get away with that. The other day I wore the exact outfit that I'm saying you should wear. Still jeans and a shirt, but with the sexy strappy shoes I was wearing and the pretty blouse, I was getting compliments left and right.

 

I second the push up bra. Made my boobs jiggle and spill out the top.

 

And I was still

Comfortable and felt like myself.

 

I have no advice on makeup. If I didn't wear makeup, my face could stop a clock , I think. If you don't usually wear it, just wear a tad. Lip gloss and mascara at least.

[No_Go]

You're right, I missed the last sentence:)

 

For the VS push-ups, which ones would you suggest? My ex will always whine for the Very Sexy series (I never tried the really padded ones like the Bombshell series,... but he'd still complain so I switched to Lightly lined VSs for him...)

 

I think Tetrahedral meant men do not notice make up details which I agree. Kim K wears hell of a contour, highlight etc, but I've heard men referring to her make-up as light and natural Scarlet J make up, albeit not natural, is not that heavy but men notice she wears it for her red lips, not the rest. I feel like men note prominent features + shape and very little detail...

 

The OP should do what I suggested in my last sentence, which was do what feels comfortable for her

 

Since she said she likes to transform herself...I figured why not dress to the 9's?

 

Push upbras only have padding on the underside of the bra...hence the push up effect and if you get a well made bra like VS...it would feel fine to the guy if it were to get to that point

 

I love the flair fit skirts and dresses too No Go!

 

Detail is not lost on men. Look at famous entertainment figures, Scarlett Johanson, Angelina Jolie and the ever so useless Kim Kardasian They put themselves together flawlessly and the result.... *man drops jaw* I love seeing that look on my dates face but if the OP doesnt want to go that route...thats totally fine

[smackie9]

Guys do notice painted toes...get a pedi.

[thefooloftheyear]

Ooooooooo!!!! Yay!

 

 

 

One final tip....dont show too much boobs. You want to show a little but not like...heyyyy look at my chest all night!

 

 

Shhh!......:laugh:

 

 

TFY

[CautiouslyOptimistic]

Shhh!......:laugh:

 

 

TFY

 

Hahaha! I'm cracking up, especially because the look on my face when I read "push up bra" was like "no freaking way!"

 

(OP, unless you need the extra "uumph" I'd save that for the bedroom )

[No_Go]

I'm wondering what kind of shoes will men like for a date?

 

Heels is the obvious choice but it doesn't really fit op's style.

Flat strappy sandals? Wedges? Some brighter color low heeled accent shoes?

 

If she goes for heels though they can lift up jeans/top outfit to sufficiently dressy. I'm thinking wedges may as well but I never asked guys how they feel about wedges.