If your friend is coming from apple picking then why are you trying to get a full head of hair and a full face of makeup done? Wear what makes you feel awesome, be it jeans or a dress.

The key will be your hair. Get your hair done. They’ll be looking at your face, more than your clothes. Especially if you get there first.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:Designer straight leg jeans (AG, mother), trendy sneakers, top from Reformation

This is what I’d wear. Just make sure the sneaks aren’t golden goose because then you look try hard (and like a trend whore with no financial sense) not effortless.

Oh hell no! No sneakers on a Saturday night. If it were a day thing- fine.

Sneakers after dark fur drinks on a woman are not cool, definitely not sexy. Wtf?!

I live out west. We do things differently. You’ll routinely see fashion sneakers out here.

This is also the look in NYC. Heels are very try-hard these days.

Anonymous wrote:A flared dress, high heels (probably boots) and an it girl handbag.

None of this. Absolutely none of it.

What is your body type

This is op. I wear a lot of dresses but I think I want pants for this. My friend is coming from apple picking and will be wearing jeans.

I'm not cancelling. I'm honestly in a good place and the middle school bully doesn't have power over me anymore. Okay, I guess I wouldn't think much about what to wear of that was 100% true, but I'm not going to let that stop me. I just want my outsides to reflect my inner confidence. I've focused mostly on work clothes so don't have much for going out that fits well right now.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:Designer straight leg jeans (AG, mother), trendy sneakers, top from Reformation

This is what I’d wear. Just make sure the sneaks aren’t golden goose because then you look try hard (and like a trend whore with no financial sense) not effortless.

Oh hell no! No sneakers on a Saturday night. If it were a day thing- fine.

Sneakers after dark fur drinks on a woman are not cool, definitely not sexy. Wtf?!

You can do Air Force ones or vans because it signals you know what you are doing with fashion, but yes leave your mom tennies at home.

https://www.zara.com/us/en/ruffled-print-dress-p09137829.html?v1=211200650&v2=2111785

https://www.zara.com/us/en/hi-rise-long-length-straight-leg-z1975-jeans-p08527164.html?v1=221311270&v2=2111785

I'd wear this with black booties

https://www.zara.com/us/en/high-waisted-pants-p07901532.html?v1=222105923&v2=2113807

These pants with white air force ones, a white long sleeve shirt and a leather jacket https://www.zara.com/us/en/trf-straight-cargo-pants-p05520265.html?v1=221311101&v2=2113807

This is a fit and flare dress, I'd wear over the knee boots https://www.macys.com/shop/product/jessica-howard-womens-cable-knit-mock-neck-sweater-dress?ID=14899450&CategoryID=5449&isDlp=true

These pants are cool, you just need black boots (dr martin type) and black top https://www.zara.com/us/en/zw-the-marine-straight-jeans-p08246249.html?v1=203180350&v2=2113758

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:Designer straight leg jeans (AG, mother), trendy sneakers, top from Reformation

This is what I’d wear. Just make sure the sneaks aren’t golden goose because then you look try hard (and like a trend whore with no financial sense) not effortless.

Oh hell no! No sneakers on a Saturday night. If it were a day thing- fine.

Sneakers after dark fur drinks on a woman are not cool, definitely not sexy. Wtf?!

I live out west. We do things differently. You’ll routinely see fashion sneakers out here.

Anonymous wrote:

Anonymous wrote:Designer straight leg jeans (AG, mother), trendy sneakers, top from Reformation

This is what I’d wear. Just make sure the sneaks aren’t golden goose because then you look try hard (and like a trend whore with no financial sense) not effortless.

Oh hell no! No sneakers on a Saturday night. If it were a day thing- fine.

Sneakers after dark fur drinks on a woman are not cool, definitely not sexy. Wtf?!

Anonymous wrote:Designer straight leg jeans (AG, mother), trendy sneakers, top from Reformation

This is what I’d wear. Just make sure the sneaks aren’t golden goose because then you look try hard (and like a trend whore with no financial sense) not effortless.

I’m just flabbergasted here. It’s a monthly catch up, so the main person is a really good friend. The other people are just in town for a few days. Skip it! Just say, “friend, Out Of Town Larla was a real b to me in middle school and it may seem silly, but I just want to steer clear. Could you make an excuse for me? Say my kid has covid or something. Have a great time and I’ll see you next month.” OOT Larla doesn’t live here! Who cares?

If you feel like you need different clothes to hang out with them, just skip it. Why would you do that to yourself??

Anonymous wrote:

Anonymous wrote:A flared dress, high heels (probably boots) and an it girl handbag.

what in the hell does any of this mean

This sounds really dated and try hard and the opposite of "effortlessly cool"

Good luck, OP. I think you're going to struggle with the "effortlessly cool" part. But hey, at least you're "accomplished".