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

[Anonymous]

I would wear black. Universally flattering and cool and collected. I would focus on good hair and makeup since you will probably be sitting down and people won't be able to see your lower half. Focus on understated but expensive jewelry. Think diamond studs over dangly earnings.

[Anonymous]

Straight leg jeans in a medium wash and a v-neck sweater in a fall color (plum, forest green, whatever color looks good on you). Boots with a not-too-high heel. Delicate jewelry and simple makeup, natural curls.

[Anonymous]

Anonymous wrote:

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.

[Anonymous]

Anonymous wrote:

Anonymous wrote:https://www.instagram.com/p/Ciu3umGOF-C/

https://www.shopltk.com/explore/cellajaneblog/posts/6eee4de7-4e89-11ed-9b1e-0242ac110004

https://www.shopltk.com/explore/cellajaneblog/posts/109f21d2-43eb-11ed-8f19-0242ac110003

The third link is great, spot on (I'd do black coat and boots but same idea).

But the first one with the leather (or plastic) pants and the strappy heels? TOO MUCH. The key to looking effortless is to avoid items that, you know, take obvious effort. That means no super high heels, and definitely not a strappy sandal in October. No fabrics that take extra effort or are very trendy. Silk or cashmere are good -- it says you like quality and generally they don't require effort to wear. Leather pants? No.

The second one involves split hem bootleg pants. Just: no. That looks like something I would have worn to a bachelorette party when I was 30. The opposite of effortless!

It all comes down to the same formula: great fitting jeans, cool but easy shoes (Chelsea boots, flats, loafers), a slightly dressy but easy top (silk button down, cashmere sweater), subtle jewelry, make sure your hair and face look good. The "cool" bit actually comes from your confidence, not the parts of your outfit. It's the ability to go out wearing nothing particularly special and still look and feel good.

I agree 100% with your last paragraph, but disagree with your takes on links #1 and #3. I wouldn't do #3 -- first, that coatigan looks like a total bathrobe on anyone who isn't very tall and thin (not how OP describes herself). And while the outfit has an effortlessly cool vibe, it doesn't have a "bar at a cool restaurant on a Saturday night" vibe. It's not try hard to elevate your look past jeans and sweater for a Saturday night out at hip restaurant.

Faux leather pants are everywhere right now, they don't say try hard, they say I'm going out on a Saturday night. (But I do agree with you that the strappy healed sandals are too much for OP's situation.) I like the coated-jeans variety -- they are less shiny. A black bootcut pair with a high waist would be flattering on OP, I bet. Then some sort of simple silk or cashmere or knit top -- tucked or french tucked. Finish with nice, but not over the top, accessories (Chelsea boot with small block heal), etc.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

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

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

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

NP. And wearing a moto jacket when that’s not your real style is just going to look odd.

[Anonymous]

Anonymous wrote:

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'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.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

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.

[Anonymous]

Anonymous wrote:

Anonymous wrote:https://www.anthropologie.com/shop/pilcro-mock-neck-cable-knit-sweater?color=011&recommendation=pdp-rightRail-sfrectray-pdprightrailsimilaritems&type=STANDARD&quantity=1

Get this sweater. Super cute and a bit cropped. If you pair with high waisted dark jeans, will make you look longer. Knee high boots to finish the look.

No. Bad advice if OP is shorter and hourglass. Stick to ONE color, preferably dark - navy or black or or grey - and shoes with a slight heel, like a bootie. (Sometimes shorter people who wear knee high boots look chopped off at the leg unless they're thin and ruler-shaped.) Wear makeup. Depending on your skin, you want tinted moisturizer (lighter coverage) or a CC cream (heavier coverage). Get your brows done and your hair freshly cut and colored. Tinted lip gloss. Stud earrings. and a simple necklace. Polish up your wedding and engagement rings. Carry a purse that looks subtly expensive.

No, no, no. All of this will look way too done. Again, these people are coming from apple picking.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:https://www.anthropologie.com/shop/pilcro-mock-neck-cable-knit-sweater?color=011&recommendation=pdp-rightRail-sfrectray-pdprightrailsimilaritems&type=STANDARD&quantity=1

Get this sweater. Super cute and a bit cropped. If you pair with high waisted dark jeans, will make you look longer. Knee high boots to finish the look.

No. Bad advice if OP is shorter and hourglass. Stick to ONE color, preferably dark - navy or black or or grey - and shoes with a slight heel, like a bootie. (Sometimes shorter people who wear knee high boots look chopped off at the leg unless they're thin and ruler-shaped.) Wear makeup. Depending on your skin, you want tinted moisturizer (lighter coverage) or a CC cream (heavier coverage). Get your brows done and your hair freshly cut and colored. Tinted lip gloss. Stud earrings. and a simple necklace. Polish up your wedding and engagement rings. Carry a purse that looks subtly expensive.

No, no, no. All of this will look way too done. Again, these people are coming from apple picking.

But OP herself is not going apple picking. OP can look casual nice, not casual farm outing.

[Anonymous]

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

[Anonymous]

OP I have a different body than you; but I feel most comfortable in my favorite jeans, booties and either a tucked-in blouse or a thin sweater. I get hot easily so the links for chunky sweaters would only work for me if sitting outdoors.

[Anonymous]

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?

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

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.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

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'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.