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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.

Anonymous wrote:

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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).

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

+1 Also very try hard, which is the opposite of what OP is going for. I would get a manicure for OP’s plan (I normally get my fingernails done once or twice a year) but keep it very neutral.

Anonymous wrote:Here’s what I’d wear. I feel most comfortable in black.

https://www.ayr.com/products/the-airport-cardi#40179193610319

https://www.madewell.com/the-curvy-perfect-vintage-jean-in-lunar-wash-NA883.html?dwvar_NA883_color=DM0682&cgid=apparel-jeans-perfectsummer#start=40

https://www.nordstrom.com/s/marc-fisher-ltd-latika-platform-loafer-women/7022655?origin=category-personalizedsort&breadcrumb=Home%2FWomen%2FShoes%2FOxfords%20%26%20Loafers&color=001

https://www.bloomingdales.com/shop/product/14k-yellow-gold-zigzag-hammered-climber-earrings-100-exclusive?ID=1391725&CategoryID=3376

And then I’d probably get my nails done, either dark green or dark red for fall/winter.

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

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).

Anonymous wrote:Here’s what I’d wear. I feel most comfortable in black.

https://www.ayr.com/products/the-airport-cardi#40179193610319

https://www.madewell.com/the-curvy-perfect-vintage-jean-in-lunar-wash-NA883.html?dwvar_NA883_color=DM0682&cgid=apparel-jeans-perfectsummer#start=40

https://www.nordstrom.com/s/marc-fisher-ltd-latika-platform-loafer-women/7022655?origin=category-personalizedsort&breadcrumb=Home%2FWomen%2FShoes%2FOxfords%20%26%20Loafers&color=001

https://www.bloomingdales.com/shop/product/14k-yellow-gold-zigzag-hammered-climber-earrings-100-exclusive?ID=1391725&CategoryID=3376

And then I’d probably get my nails done, either dark green or dark red for fall/winter.

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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'm petite with an hourglass figure. From my closet, I'd wear ankle-length washed black jeans (Madewell) to wear with a silk shirt or my cashmere v-neck sweater (wear a little black tank under ether one to show just a tad). Black suede flats or maybe ankle boots with a little heel. Gold hoops and your favorite necklace. BTW, good luck on losing the Covid weight. I did that and it has made a big difference for me, both in terms of how I look and feel.

Switching over from fashion advice to life advice -- I'm glad to hear you're in a good place, OP, but, that said, if I were you, I'd bow out. I've been to those HS reunions where I've had to confront the the jerks, and, sure, it was a nice feeling to realize that I'd left that chapter in my life far behind, but, I still didn't want to spend the night catching up with those people. I mean, I hope they also have left that chapter in their lives behind and become better people, but honestly, life is too short to waste on them when there are people I like and love much more and would rather spend time with.

Yes I feel like most people glossed over the petite hourglass and busty part. Nothing that looks good on a WASP generally transfers to a busty petite chick with a butt unless you have impeccable proportions. V-neck. Keep with fitted on one half. Make sure you follow rule of thirds. Dont wear too tight or too revealing. Make sure bra fits well and avoid good look from the front but not from the back.

Loling at the idea that all WASPSs are built the same. You must not get out much.

You know short AND curvaceous WASPs with a butt and tummy and thighs? There is a look associated with WASPs- the previous description is not it.

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

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!

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

I came here to say exactly this. Or kick flare jeans with a heeled boot. I like this sweater too: https://evereve.com/favorite-off-shoulder-51606-c

Add some dainty jewelry

Go get an on-trend mani beforehand too

I like that evereve sweater a lot. It feels elevated and effortless at the same time. What mani is "on-trend" right now?

Or choose 4 fall colors and alternate nails.

French mani but the tip is black or a fall color

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

I came here to say exactly this. Or kick flare jeans with a heeled boot. I like this sweater too: https://evereve.com/favorite-off-shoulder-51606-c

Add some dainty jewelry

Go get an on-trend mani beforehand too

What bra do you wear with that sweater - strapless, or one with a strap that you want people to see?

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Anonymous wrote:Well fitting slim/skinny/tapered black pants (skinny black jeans or J crew Ponte pants) + a fitted black shirt (artful tank in summer/flattering neckline crew or asymmetrical in winter? + denim or Moto jacket + nighttime earrings. Would aim for ankle boots but would probably end up in Rothy's because they are so comfy.

I'm not a skirt person.

Nah, not in 2022

I don't know if OP mentioned her age, but most people not in their 20s don't care if a look is a couple of years past being THE IN THING as long as it is flattering.

In general I agree, but OP wants to look "effortlessly cool." That is a fine outfit but it's not going to make you look cool in 2022

DP, but looking effortlessly cool is far more about attitude than actual outfit. It's hard to look effortlessly cool when you don't feel comfortable with what you're wearing. No one is going to look like a million bucks if the outfit doesn't suit them.

I agree that she needs an outfit that gives her confidence. I personally would not feel confident in a dated outfit with people I hadn't seen for a long time and wanted to impress. But she should certainly wear something that flatters her and that she feels comfortable and natural in.

For OP, who is a petite hourglass with some extra pounds, I think straight-leg high-waisted jeans, a tucked-in t-shirt or top, booties with a chunky heel, and a blazer on top is a cool and current outfit that is also going to be flattering.

DP but the point is for effortless cool, you don't dress to impress. Not your goal!

I don't think the outfit PP described is "dated" though it could look dated depending on your details (I would not do "evening earrings", I'd do small studs, and I would make sure the top is not too fitted). But wearing a dark column with comfortable shoes and little bit of jewelry isn't dated or current -- it's just a classic approach. Can't go wrong.

Sounds like OP is looking for a good blazer for this kind of look and if she finds one she loves, why not. But I'd make an effort not to buy any other elements of this outfit and to just wear things she has that she already feels good in. As little extra effort as possible.

I think she's been fairly clear that she wants to impress these people...? Looking effortless is not the same as actually putting in no effort, haha

DP - sure, but you also can’t look like you’re trying to impress them if you want to look effortless, too. It’s a tough balance, especially if you actually do care what they think. I think that’s the problem.

Yes, those of us saying "wear clothes you own, don't wear special items, just look nice enough to feel confident but nothing try hard" are basically saying "you do not need to impress these people, can just go as the best version of who you already are, and no further effort is needed."

Buying new clothes to celebrate your birthday, because you have an excuse to dress up, so that you can fit in at a new job, etc. -- great! Buying new clothes to try and match some idea of "effortless cool" in order to impress people who were not nice to you in high school? Not going to work, and I say this from love and experience.