Effortlessly cool "I just threw this on but look like a million bucks" outfit to go out for drinks

[Anonymous]

Anonymous wrote:

Anonymous wrote:Relaxed fit (think 90s) distressed lighter shade jeans, a men’s style blouse, and an incredibly boxy fit blazer. Pair it with a Justin cowboy boots. Think Hailey Bieber.

Lol this is an outfit that could be pulled off by like .0001% of women over the age of 35. And I say that as a woman over the age of 35. You have to be tall, thin, and incredibly beautiful for this to work (i.e. you have to be Hailey Bieber).

Actually, I saw pictures of Cindy Crawford and a similar outfit as this one is described and she looks fantastic. She is definitely older than 35, too.

[Anonymous]

Would really like an update from OP.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:Relaxed fit (think 90s) distressed lighter shade jeans, a men’s style blouse, and an incredibly boxy fit blazer. Pair it with a Justin cowboy boots. Think Hailey Bieber.

Lol this is an outfit that could be pulled off by like .0001% of women over the age of 35. And I say that as a woman over the age of 35. You have to be tall, thin, and incredibly beautiful for this to work (i.e. you have to be Hailey Bieber).

Actually, I saw pictures of Cindy Crawford and a similar outfit as this one is described and she looks fantastic. She is definitely older than 35, too.

She’s CINDY CRAWFORD

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:French main with black tip? I haven’t seen this but it sounds gross like you’ll look like you’ve been digging in dirt

Stick to your skinny jeans and red nails.

NP and I agree…these nails always look tacky and gross to me. And I love fun colors, just think the French manicure in black/brown/etc look gross.

Red nails look gross and tacky?

Nothing could be more classic but okayyyyyyyy

No, you're confused...the PP thought the black-tip manicures were tacky and gross, not the red nails.

Lol. The blind leading the blind over here.

[Anonymous]

wear good/expensive jewelry , purse, shoes and jacket. Makes the biggest impression when entering the establishment and when holding your drink.

[Anonymous]

I think a bag says it all. I prefer an Hermès Evelyne. It’s effortlessly cool to use your verbiage. Also, with this fact you can intentionally dress down and still feel confident.

[Anonymous]

Anonymous wrote:

Anonymous wrote:Bonus points if it hides a hypothetical extra 19 pounds one hasn't been able to shake since covid, a lot on a petite hourglass frame.

I wanna be your friend. Damn those 19 lbs

Thank you!

[Anonymous]

Anonymous wrote:OP - what did you end up wearing, and how was the evening?

This is op. Thanks for asking. It was a lot of fun. We enjoyed reminiscing and I enjoyed feeling like my bully no longer had power over me anymore.

I appreciated the advice on this thread. Without it I would have tried too hard with a fit and flare dress and heels. Or like a belted prairie dress and tall boots that looked good in my mind but not so much in my reflection out of the house. Instead I went with jeans and my favorite sweater and a nice cashmere coat on top since the plan was to stay in the patio. Chelsea boots. I was warm and comfortable and felt like myself! And since I like myself more than I did in high school it was all good. My bully was much more made up and in something probably way more trendy, but that's fine. She was always more into trends than me, which used to make me feel inadequate but now it seems insignificant. And she looked cold

[Anonymous]

Anonymous wrote:

Anonymous wrote:OP - what did you end up wearing, and how was the evening?

This is op. Thanks for asking. It was a lot of fun. We enjoyed reminiscing and I enjoyed feeling like my bully no longer had power over me anymore.

I appreciated the advice on this thread. Without it I would have tried too hard with a fit and flare dress and heels. Or like a belted prairie dress and tall boots that looked good in my mind but not so much in my reflection out of the house. Instead I went with jeans and my favorite sweater and a nice cashmere coat on top since the plan was to stay in the patio. Chelsea boots. I was warm and comfortable and felt like myself! And since I like myself more than I did in high school it was all good. My bully was much more made up and in something probably way more trendy, but that's fine. She was always more into trends than me, which used to make me feel inadequate but now it seems insignificant. And she looked cold

What kind of purse/bag did she have? Just out of curiosity?

By the way it sounds like you were the perfect outfit and looked beautiful.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:OP - what did you end up wearing, and how was the evening?

This is op. Thanks for asking. It was a lot of fun. We enjoyed reminiscing and I enjoyed feeling like my bully no longer had power over me anymore.

I appreciated the advice on this thread. Without it I would have tried too hard with a fit and flare dress and heels. Or like a belted prairie dress and tall boots that looked good in my mind but not so much in my reflection out of the house. Instead I went with jeans and my favorite sweater and a nice cashmere coat on top since the plan was to stay in the patio. Chelsea boots. I was warm and comfortable and felt like myself! And since I like myself more than I did in high school it was all good. My bully was much more made up and in something probably way more trendy, but that's fine. She was always more into trends than me, which used to make me feel inadequate but now it seems insignificant. And she looked cold

What kind of purse/bag did she have? Just out of curiosity?

By the way it sounds like you were the perfect outfit and looked beautiful.

Thanks I honestly don't remember her purse.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:OP - what did you end up wearing, and how was the evening?

This is op. Thanks for asking. It was a lot of fun. We enjoyed reminiscing and I enjoyed feeling like my bully no longer had power over me anymore.

I appreciated the advice on this thread. Without it I would have tried too hard with a fit and flare dress and heels. Or like a belted prairie dress and tall boots that looked good in my mind but not so much in my reflection out of the house. Instead I went with jeans and my favorite sweater and a nice cashmere coat on top since the plan was to stay in the patio. Chelsea boots. I was warm and comfortable and felt like myself! And since I like myself more than I did in high school it was all good. My bully was much more made up and in something probably way more trendy, but that's fine. She was always more into trends than me, which used to make me feel inadequate but now it seems insignificant. And she looked cold

What kind of purse/bag did she have? Just out of curiosity?

By the way it sounds like you were the perfect outfit and looked beautiful.

Thanks I honestly don't remember her purse.

Purse people always think other people notice their purse and we never do lol

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:I’d probably wear straight leg jeans, boots with a small heel or Chelsea boots, and a sweater I can tuck in on the front, and great lipstick. Like this -

https://www.everlane.com/products/womens-day-boot-ecru?collection=womens-boots

https://www.onequince.com/women/100-organic-fisherman-crew-sweater

What a great sweater - and what a great price!

PP here - I have it and compared it to the jenni kayne sweater and they’re almost identical!

Agree! I loooove the jenni fisherman crew sweater but the quince is nearly identical - not the same color palatte tho (which is something i love about jenni kayne).

The Quince sweater comes in a cashmere version (the one linked above is the cotton version). It's only a little pricier, still under $100, and comes in a more subtle color palette. Still not quite as refined as the JK but a little closer of a dupe for a steal.

I say this as someone who has absolutely no problem paying $$$$ for high quality fashion items, and purchases such items plenty, but I really do think JK is over-priced.

And super basic.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:OP - what did you end up wearing, and how was the evening?

This is op. Thanks for asking. It was a lot of fun. We enjoyed reminiscing and I enjoyed feeling like my bully no longer had power over me anymore.

I appreciated the advice on this thread. Without it I would have tried too hard with a fit and flare dress and heels. Or like a belted prairie dress and tall boots that looked good in my mind but not so much in my reflection out of the house. Instead I went with jeans and my favorite sweater and a nice cashmere coat on top since the plan was to stay in the patio. Chelsea boots. I was warm and comfortable and felt like myself! And since I like myself more than I did in high school it was all good. My bully was much more made up and in something probably way more trendy, but that's fine. She was always more into trends than me, which used to make me feel inadequate but now it seems insignificant. And she looked cold

What kind of purse/bag did she have? Just out of curiosity?

By the way it sounds like you were the perfect outfit and looked beautiful.

Thanks I honestly don't remember her purse.

Purse people always think other people notice their purse and we never do lol

This is the truth. Also just brand logo people in general. I'm not looking closely enough at any of your clothes to know what brand they are! And if something you are wearing catches my eye enough to wonder what brand it is, I just ask. And from experience, I know the answer is as likely to be a chagrined "Oh, actually... I got this at Target" or bewildered "huh I've had this forever I think I got it at a thrift store" as "Yes, it's Chanel." Like as much as people want to believe their most expensive, highest end clothes are being admired far and wide, that's often not the case.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:OP - what did you end up wearing, and how was the evening?

This is op. Thanks for asking. It was a lot of fun. We enjoyed reminiscing and I enjoyed feeling like my bully no longer had power over me anymore.

I appreciated the advice on this thread. Without it I would have tried too hard with a fit and flare dress and heels. Or like a belted prairie dress and tall boots that looked good in my mind but not so much in my reflection out of the house. Instead I went with jeans and my favorite sweater and a nice cashmere coat on top since the plan was to stay in the patio. Chelsea boots. I was warm and comfortable and felt like myself! And since I like myself more than I did in high school it was all good. My bully was much more made up and in something probably way more trendy, but that's fine. She was always more into trends than me, which used to make me feel inadequate but now it seems insignificant. And she looked cold

What kind of purse/bag did she have? Just out of curiosity?

By the way it sounds like you were the perfect outfit and looked beautiful.

Thanks I honestly don't remember her purse.

Purse people always think other people notice their purse and we never do lol

So true!

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:I’d probably wear straight leg jeans, boots with a small heel or Chelsea boots, and a sweater I can tuck in on the front, and great lipstick. Like this -

https://www.everlane.com/products/womens-day-boot-ecru?collection=womens-boots

https://www.onequince.com/women/100-organic-fisherman-crew-sweater

What a great sweater - and what a great price!

PP here - I have it and compared it to the jenni kayne sweater and they’re almost identical!

Agree! I loooove the jenni fisherman crew sweater but the quince is nearly identical - not the same color palatte tho (which is something i love about jenni kayne).

The Quince sweater comes in a cashmere version (the one linked above is the cotton version). It's only a little pricier, still under $100, and comes in a more subtle color palette. Still not quite as refined as the JK but a little closer of a dupe for a steal.

I say this as someone who has absolutely no problem paying $$$$ for high quality fashion items, and purchases such items plenty, but I really do think JK is over-priced.

And super basic.

Op here. I kind of glossed over this repeated sweater recommendation because I couldn't see what was special about it. I had a bunch of sweaters like that back in high school. I did look up Jenni Kayne but wasn't inspired by anything. The styles look like 90s throwbacks but at a much higher price point than we used to pay. And more for taller, straighter silhouettes.