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

[Anonymous]

ok, enough with the "get a blowout" - she is meeting people coming from APPLE PICKING.
OP, are you seriously considering buying new clothes for this meeting? Think about that one for a sec.

[Anonymous]

Anonymous wrote:

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?

Damn.

I can't wait to see what other people suggest. Just glancing at the first few comments, I think a dress is too much in this situation. I would go with a very current/flattering pair of jeans. Maybe black, but blue jeans work, too.

A pretty, stylish top like this: https://www.nordstrom.com/s/sequin-keyhole-neck-blouse/7121015?origin=coordinating-7121015-0-3-PDP_1-recbot-also_viewed_graph&recs_placement=PDP_1&recs_strategy=also_viewed_graph&recs_source=recbot&recs_page_type=product&recs_seed=6473911&color=RICH%20BLACK

Black booties or something like that. Simple jewelry.

Another idea is a soft sweater in your favorite/most flattering color. Something that makes you feel great.

The sequins on that top might be a bit much for casual drinks, especially if people are coming from apple picking

[Anonymous]

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.

[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.

Mostly agree - but it really depends on the fit and your comfort. Eva in Bad Sisters had some leather pants outfits - and leather skirts outfits - that really did look effortlessly cool. I think it's a mix of the fit, the style, and her confidence/ease. Just to say if you can pull it off, then go for it.

Sharon Horgan looks great in everything, in breaking news.

[Anonymous]

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.

[Anonymous]

Anonymous wrote:

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?

Damn.

I can't wait to see what other people suggest. Just glancing at the first few comments, I think a dress is too much in this situation. I would go with a very current/flattering pair of jeans. Maybe black, but blue jeans work, too.

A pretty, stylish top like this: https://www.nordstrom.com/s/sequin-keyhole-neck-blouse/7121015?origin=coordinating-7121015-0-3-PDP_1-recbot-also_viewed_graph&recs_placement=PDP_1&recs_strategy=also_viewed_graph&recs_source=recbot&recs_page_type=product&recs_seed=6473911&color=RICH%20BLACK

Black booties or something like that. Simple jewelry.

Another idea is a soft sweater in your favorite/most flattering color. Something that makes you feel great.

please do not wear this top.

[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.

Rule of thirds rules for petite ladies! It is our credo!

[Anonymous]

Anonymous wrote:ok, enough with the "get a blowout" - she is meeting people coming from APPLE PICKING.
OP, are you seriously considering buying new clothes for this meeting? Think about that one for a sec.

Plenty of blowouts look really natural. Getting one just means her hair will look smooth, bouncy, and frizz-free. And nothing wrong with buying new clothes if OP is going to wear them again.

[Anonymous]

Anonymous wrote:Straight leg jeans, Chelsea boots, a lightweight v-neck sweater, and simple gold jewelry. Also, good hair and killer lipstick.

Pretty much agree with all of this.

[Anonymous]

Anonymous wrote:ok, enough with the "get a blowout" - she is meeting people coming from APPLE PICKING.
OP, are you seriously considering buying new clothes for this meeting? Think about that one for a sec.

I agree with this. I'd shop my closet and wear clothes that are flattering but made me feel good.

I think part of what is happening here is that OP wants to *feel* effortlessly cool in front of these people who make her feel uncool. It's not really about the outfit. Which is why advice to wear clothes that require a certain level of effort are a bad idea. These will just make her feel more like a try-hard.

Honestly, if this drinks plan is something OP really wants to do, here's what I'd do:

Where my favorite casual jeans outfit, reasonably comfortable shoes (flats or flat boots), some cute jewelry and do my hair as I normally would to meet my friend for drinks (no salon blowout, but I might make a little extra effort to ensure it's not like third day ponytail hair).

Make a dinner reservation for a nearby but low-key restaurant about an hour after I'm supposed to meet for drinks, with my DH.

Show up 10-15 minutes late, be charming for about 50 minutes while drinking one drink, asking lots of questions, and being friendly and chill.

Leave.

And scene.

[Anonymous]

^Wear not where

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:Designer straight leg jeans (AG, mother), trendy sneakers, top from Reformation

This is what I’d wear. Just make sure the sneaks aren’t golden goose because then you look try hard (and like a trend whore with no financial sense) not effortless.

Oh hell no! No sneakers on a Saturday night. If it were a day thing- fine.

Sneakers after dark fur drinks on a woman are not cool, definitely not sexy. Wtf?!

I live out west. We do things differently. You’ll routinely see fashion sneakers out here.

Agreed; fashion sneakers are having a moment.

[Anonymous]

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.

[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

Wow, the 1980's Forenza sweater from the Limited making the rounds!

Ha! We used to we the V-neck Forenza backwards in HS. I forgot all about the Forenza sweater. Thanks for making me smile

[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

Wow, the 1980's Forenza sweater from the Limited making the rounds!

Ha! We used to we the V-neck Forenza backwards in HS. I forgot all about the Forenza sweater. Thanks for making me smile

*wear