Obviously NWR but I have a date tonight,... UPDATE in comments

lacqueredlover

And I have no idea what to wear.  And I'm freaking out a bit because it's weird to even think about dating but I just gotta go for it and see what happens.  If I'm not ready, I'll hold off again.

So, what do I wear?  It's at a wine/scotch lounge so I don't think my usual jeans and flats will go.

And am I not supposed to wear lipstick?  I always wear lipstick but 2 of my friends told me not to haha.

HELP ME I AM A DISASTER

RebeccaFlower

Why no lipstick? Can you show pictures of options you have? I would probably just switch our your flats for some heeled booties. 

PS- I've followed your story and I am so glad you're exploring yourself. You are so classy. 

AlexisA01

How about a dress? Maybe with some nice heeled boots or pumps. Very nice blouse with a pencil skirt or some skirt. Wear your lipstick!! :-)

theartistformerlyknownas

Are they expecting a high school-style makeout sesh where you eat half his face? That's the only reason I can see to not wear lipstick. Wear it!

A little chilly there tonight, I'd go cute skirt and boots, black top.

KatieinBkln

Wear lipstick but only if you have a nice longwear that won't come off on your wine glass!

As for the outfit, I'd go with a skirt and killer booties in this weather--a nod to spring trying to happen, but still keeping those feet warm. Alternatively, black skinny jeans and a top that makes you feel smokin', plus killa heels. I wouldn't wear a dress, oddly--wine/scotch bar reads "cool girl" to me, and a dress might be a bit too pretty and precious in this setting.

Ultimately though, whatever you wear should be the kind of thing that makes you feel awesome and beautiful and powerful! You must have a go-to in that realm.

HAVE FUN! (And check in with us later so we know you haven't been abducted by a scotch-loving perv. Kidding. Check in because we're nosy).

lacqueredlover

Thanks @RebeccaFlower !

I honestly don't even know where to start.  And everyone seems to tell me that the bright or dark lipsticks I wear are intimidating (but come on I blog about makeup!)  And that it will be a turn off to a kiss but I'll be honest, I'm not sure I mind that.

southernbelle0915

@PrettyGirlLost.... where are you with your polyvore genius?

ETA: I don't find any hidden meaning in lipstick, I just don't really like dark lipstick in general. I think there are VERY few people who can pull it off well.

novella1186

Yay! Good luck, I hope it's at least fun! 

I would go with dark skinny jeans, a nice pair of heels, and a cute t-shirt with a fancy necklace. That way you're a little more dressed up, but not "trying too hard" ya know? 

Or if that doesn't sound dressy enough for this place, a simple/cute cocktail dress? 

Here's some inspiration:

This one even suggests undies! lol 

RebeccaFlower

lacqueredlover said:

Thanks @RebeccaFlower !

I honestly don't even know where to start.  And everyone seems to tell me that the bright or dark lipsticks I wear are intimidating (but come on I blog about makeup!)  And that it will be a turn off to a kiss but I'll be honest, I'm not sure I mind that.

I call serious bullshit on that. I think you should wear your makeup however you feel most confident. 

PS- I've wanted to ask you for a while, recs for a beginner lipstick wearer? I literally own one 4 year old tube but I recently changed my hair to brunette from a (fake) red, so I'd like to explore. 

lacqueredlover

KatieinBkln said:

Wear lipstick but only if you have a nice longwear that won't come off on your wine glass!

As for the outfit, I'd go with a skirt and killer booties in this weather--a nod to spring trying to happen, but still keeping those feet warm. Alternatively, black skinny jeans and a top that makes you feel smokin', plus killa heels. I wouldn't wear a dress, oddly--wine/scotch bar reads "cool girl" to me, and a dress might be a bit too pretty and precious in this setting.

Ultimately though, whatever you wear should be the kind of thing that makes you feel awesome and beautiful and powerful! You must have a go-to in that realm.

HAVE FUN! (And check in with us later so we know you haven't been abducted by a scotch-loving perv. Kidding. Check in because we're nosy).

My problem is that I've been losing weight so a lot of my clothes are too big on me now!

I could do black skinny jeans and a flowy shirt that shows a bit of my baby cleavage.  I have mid calf slouchy grey heeled boots I can wear or actual high heels I guess (I so rarely wear heels, guess I'm gonna get back into it.)

I need a stylist haha.

lacqueredlover

I legit dont' own any cute skirts.  Is that weird?  I feel like I don't know how to dress myself.  

lacqueredlover

RebeccaFlower said:

lacqueredlover said:

Thanks @RebeccaFlower !

I honestly don't even know where to start.  And everyone seems to tell me that the bright or dark lipsticks I wear are intimidating (but come on I blog about makeup!)  And that it will be a turn off to a kiss but I'll be honest, I'm not sure I mind that.

I call serious bullshit on that. I think you should wear your makeup however you feel most confident. 

PS- I've wanted to ask you for a while, recs for a beginner lipstick wearer? I literally own one 4 year old tube but I recently changed my hair to brunette from a (fake) red, so I'd like to explore. 

When I decided I wanted to start wearing bright and dark lipsticks, I literally just jumped right in.  Try the Revlon matte color balms, great colors, wear well, not too pricey and lots of colors to choose from.

lovegood90

I agree with the PPs who said dark skinny jeans, a nice shirt and heels! I feel like that's a foolproof outfit without trying too hard. Also I think you should wear your makeup however you want, so that you're the most comfortable/confident.

Good luck!!

novella1186

lacqueredlover said:

I legit dont' own any cute skirts.  Is that weird?  I feel like I don't know how to dress myself.  

Totally not weird. For some reason I seem to have an aversion to skirts, so I own 1 cute one and I've never worn it. I would stick with the black skinny jeans and a comfy pair of heels (if you have a comfy pair) 

climbingsingle

A casual dress with boots? 

Wear lipstick. 

lacqueredlover

Ok so if I go with cool girl black skinny jeans and a top, heels or heeled boots?  It's only in the 40's here.  I so wish it was leather jacket weather.  I always feel cool and confident in my leather jacket.  Most of the rest of the time I feel like a mess

southernbelle0915

Heeled boots!

novella1186

lacqueredlover said:

Ok so if I go with cool girl black skinny jeans and a top, heels or heeled boots?  It's only in the 40's here.  I so wish it was leather jacket weather.  I always feel cool and confident in my leather jacket.  Most of the rest of the time I feel like a mess

Whichever you're better at walking in! I think either would be cute. But I've seen girls struggling to walk in heels or stumbling or you can tell they're uncomfortable, and it ain't cute. This is why I usually avoid heels. I'm not too great in walking in them and I don't want to make a fool of myself lol 

lacqueredlover

climbingwife said:

A casual dress with boots? 

Wear lipstick. 

That was the other option.  I have a cute short sleeved cobalt blue lace dress that I can wear with dark opaque tights and ankle boots.  But I feel like it looks better with the aforementioned leather jacket that it is too cold to wear.

theartistformerlyknownas

lacqueredlover said:

Thanks @RebeccaFlower !

I honestly don't even know where to start.  And everyone seems to tell me that the bright or dark lipsticks I wear are intimidating (but come on I blog about makeup!)  And that it will be a turn off to a kiss but I'll be honest, I'm not sure I mind that.

I've had so many people tell me to tone down __________ because it's intimidating. FUCK THAT. If you're scared, you're just not the dude for me. And the same should go for your lipstick. It's a part of who you are, and you're not going to change it for someone, so you shouldn't start now.

I'd go slinky, dark colors for a "lounge."

         

lacqueredlover

Actually the lipstick I have on today is just bright, not dark, was testing a new collection and I"m not redoing my makeup for later.

climbingsingle

lacqueredlover said:

climbingwife said:

A casual dress with boots? 

Wear lipstick. 

That was the other option.  I have a cute short sleeved cobalt blue lace dress that I can wear with dark opaque tights and ankle boots.  But I feel like it looks better with the aforementioned leather jacket that it is too cold to wear.

Hmm. Then I'd do the dark skinny jeans with heeled boots. 

lacqueredlover

lolo883 said:

lacqueredlover said:

Thanks @RebeccaFlower !

I honestly don't even know where to start.  And everyone seems to tell me that the bright or dark lipsticks I wear are intimidating (but come on I blog about makeup!)  And that it will be a turn off to a kiss but I'll be honest, I'm not sure I mind that.

I've had so many people tell me to tone down __________ because it's intimidating. FUCK THAT. If you're scared, you're just not the dude for me. And the same should go for your lipstick. It's a part of who you are, and you're not going to change it for someone, so you shouldn't start now.

I'd go slinky, dark colors for a "lounge."

         

OK I legit have the booties in that last pic haha but there is still ice on the ground in NYC so not happening tonight.

blabla89

You can't possibly go wrong with a LBD, cute flats and statement jewelry. Personally I'm a sucker for a  berry colored lip stain.

levioosa

Wear the lipstick and don't overthink it!  Lolo was spot on. If someone is going to run because they're scared of the color of your lipstick, then they are not the person for you.  Have a great time tonight!  

lacqueredlover

levioosa said:

Wear the lipstick and don't overthink it!  Lolo was spot on. If someone is going to run because they're scared of the color of your lipstick, then they are not the person for you.  Have a great time tonight!  

In all fairness, my lipsticks scare me sometimes haha, but I'm not going to do like goth purple tonight.  I was thinking more rosy.

VulgarGirl

The last time I went on a first date was 10 years ago. I wore deep red lipstick. Almost black. It did not send her running screaming into the night so...I think a bold/bright lipstick should be safe.

novella1186

If the guy is intimidated by something as silly as lipstick, then he's a little bitch anyway. Let him run. 

mikenberger

Maybe not wearing lipstick has to do with the lipstick sticking to the glass or sometimes lipstick can influence the taste of what we drink?

chibiyui

Yay date!

I agree with the consensus of dark skinny jeans "cool girl" rocker chic. Maybe booties with a chunky heel?

KatieinBkln

lacqueredlover said:

Ok so if I go with cool girl black skinny jeans and a top, heels or heeled boots?  It's only in the 40's here.  I so wish it was leather jacket weather.  I always feel cool and confident in my leather jacket.  Most of the rest of the time I feel like a mess

Heeled boots would be my choice tonight. 

If you can't wear your leather, wear a blazer--it always makes me feel like a real grown-up when I wear a blazer.

Re: "lipstick is intimidating": And? If someone is intimidated by your fucking lips then he is, to quote the great Destiny's Child, a SCRUB.