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

[Anonymous]

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?

French mani but the tip is black or a fall color

[Anonymous]

Anonymous wrote:

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.

Exactly! I actually have that Evereve sweater linked above and for me, it would be ideal for this kind of thing - because *I* feel fabulous in it. But I'm not the OP. This stuff is so personal.

[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

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

[Anonymous]

Anonymous wrote:

Anonymous wrote:

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.

Exactly! I actually have that Evereve sweater linked above and for me, it would be ideal for this kind of thing - because *I* feel fabulous in it. But I'm not the OP. This stuff is so personal.

For those of you with evereve sweater - what color? I see that other stores have the same sweater in a few more colors as well

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

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.

Exactly! I actually have that Evereve sweater linked above and for me, it would be ideal for this kind of thing - because *I* feel fabulous in it. But I'm not the OP. This stuff is so personal.

For those of you with evereve sweater - what color? I see that other stores have the same sweater in a few more colors as well

PP you're quoting - I got it from Poshmark in lavendar and grey.

[Anonymous]

They will Probably focus on your extra pounds.

[Anonymous]

Anonymous wrote:Definitely go with the rule of thirds!

If you want to look effortless, no dresses (I think sleeveless dresses work well as casual in the summer and sweater dresses in the winter can also work but fall and spring are tricker for some reason)

Shoes: something with a heel or wedge that can you can easily in (definitely do not choose shoes you might trip in!)

Jeans for sure. Higher waisted is the look these days but choose a pair that flatter your body

I’m anti sweater as they can look bulky/matronly easily. How are your arms? I would do a sleeveless shirt and a fitted jacket.

In fact, I am realizing the above look is what I wore out to dinner last night with friends

I too am anti sweater because feeling cool physically helps with mental cool. Hot and stuck in sweater at crowded bar = flustered

[Anonymous]

A look that I always think looks effortless and polished when I see it on others is: great blazer, silk cami or crisp layering tank, dark rinse straight jeans, and chelsea boot. But then I try to emulate it on myself - a thin, petite hour glass - and it does me no favors. It hides my small waist and makes me look wider than I am. YMMV, OP, and if so, this is a nice look.

[Anonymous]

Anonymous wrote:This is op. This thread has been useful! I'm still not 100% sure what to wear but appreciate the guidelines. Seriously I would probably put on something like that sequined shirt or a fit and flare dress and then feel way overdressed. I have very curly hair so definitely no blowout or I really won't look like myself.

I looked up the rule of thirds and found this: https://jolynneshane.com/fashion-tips-understanding-the-rule-of-thirds.html
I probably break that rule with too long tops, so appreciate the photos making it clear why it works.

I like the idea of the tonal dressing. The green on green shirt/blazer sounds nice. My current work blazers don't work with jeans. They look like I'm wearing half a suit. Where's a good place in DC to try on lots of casual blazers? Preferably with petite options? I think I need at least two buttons or my chest busts out in a weird way. And where are good places to try on a bunch of jeans styles and nice tops? I work near a Nordstrom Rack, but their tops were uninspiring when I popped in quickly yesterday.

I should have saved my 90s forenza sweater LOL, though to me that looks a little too casual for a nice bar. More like a football game wear.

Regardless, since I haven't bought casual clothes other than workout clothes since pre pandemic, I will get some mileage out of these ideas. Thank you!

Not sure if they are petite, OP, but club Monaco has some great blazers at the moment. You could also look at Shopbop

[Anonymous]

Anonymous wrote:

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.

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.

[Anonymous]

I think this is mostly about what you have that looks great on you. For me, I’d do either a wrap dress or dark jeans, boots or booties, and a fitted white button down I have. I’ve had that shirt tailored for my body and I know it looks great. You probably have a couple of items you know you get compliments in— wear one of those.

I’d spend extra time on hair and makeup. For me that means blow drying my wavy hair straight and then putting in large hot rollers to get perfect loose curls. Makeup, falsies if you can put them on well.

You’ll be sitting for drinks I assume so focus on your top half. Show a little skin with a lower neckline and wear earrings. Have fun & be confident. No one is the same person they were in high school just consider these people new acquaintances

[Anonymous]

Anonymous wrote:

Anonymous wrote:

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.

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

[Anonymous]

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?

French mani but the tip is black or a fall color

Or the chocolate glazed donut

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

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.

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.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

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.

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.