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

[Anonymous]

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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.

Agree with your op.

[Anonymous]

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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.

Hey, be kind to us purse people! We’re not all brand whores haha. I always notice women’s purses (jewelry too), and could probably name some obscure designers and models most people can’t, but I just genuinely love handbags. Trust me, I’m just excited about a new Polene design as I am about a horseshoe Kelly.

[Anonymous]

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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

This is PP - and go OP! Sounds like you wore the perfect outfit for the occasion - and came out of this whole thing feeling even better than you went in. I'm so glad for you.

[Anonymous]

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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

This is PP - and go OP! Sounds like you wore the perfect outfit for the occasion - and came out of this whole thing feeling even better than you went in. I'm so glad for you.

Thank you!

[Anonymous]

Anonymous wrote:What do you wear when you want to look great but like you didn't have to try hard to achieve that greatness? Smart casual edition.

In other words, when you're an accomplished 42 year old woman supposed to go out for drinks on Saturday night in a cool restaurant bar with a friend for your monthly catch up session and she asks if it's okay if she brings along a couple other people who are just in town for a couple days and you say "sure, the more the merrier!" but then you find out that couple other people are none other than the girl who tortured you for being uncool in middle school and the guy who turned you down for a Sadie Hawkins dance in ninth grade...what do you wear?

COVID 19 and skip. Life if too short to spend with people you are no longer forced to spend time with. Also makes me wonder about your friend

[Anonymous]

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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

Right? When PP said .0001% of women, that’s basically Cindy Crawford. I bet Christy Turlington would rock that look too, lol.

[Anonymous]

Anonymous wrote: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.

OP can be insanely confident and a damn BOSS without needing the security blanket of an expensive purse.

[Anonymous]

Anonymous wrote: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.

"

"Effortlessly cool' is being dropped left and right but sorry, you just demonstrated what's not effortless nor cool: investing time and money in getting a brand name lady purse that everyone will recognize and then walking around dressed in their "doing my laundry" clothes as if a name brand bag is a savior and a proof of style and class.
It is not; it's tacky.

[Anonymous]

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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

Perfect outcome, OP! Glad you had fun!