Effortlessly cool "I just threw this on but look like a million bucks" outfit to go out for drinks
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Anonymous
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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? |
Anonymous
| I’m not the OP but I wish someone stylish would reply to this. I’d love to see their ideas. |
Anonymous
| 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. |
Anonymous
| A flared dress, high heels (probably boots) and an it girl handbag. |
Anonymous
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The jeans that my butt looks best in (for me a high waisted pair with straight legs, but it's going to vary by your body and preference), a mens button down or v-neck cashmere sweater, some delicate jewelry (tiny studs but sparkly, a thin gold chain with a small pendant, my wedding rings), my best evening makeup, hair down and loose and soft, booties or heels with a chunky heel (depending on weather).
You could also break out a great casual midi dress and heels, but this will come off as trying even if you look amazing. Which is why I'd downplay your clothes and just for great hair and your best face, some subtle but beautiful jewelry. Oh, and whiten your teeth. |
Anonymous
what in the hell does any of this mean |
Anonymous
| Dont go out with those aholes. |
Anonymous
+1 |
Anonymous
| Designer straight leg jeans (AG, mother), trendy sneakers, top from Reformation |
Anonymous
| Hard pass on going out with bullies from the past. Why waste your time with jerks? People dont change and you wont come out of this without a new issue. |
Anonymous
I mean…this is stuff that happened 30 years ago. It’s entirely possible these two have become non-aholes since middle school. |
Anonymous
Nope - very very likely they will hurt her feelings again. |
Anonymous
| They might be fine but if the goal was to catch up with friends and they are going to mess with that vibe, I'd pasz |
Anonymous
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Anonymous
🤣🤣🤣😂😂🤣🤣🤣 |