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: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.

Lol. It’s straight out of the Golden Girls.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

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.

Lol. It’s straight out of the Golden Girls.

Agreed, I cannot believe the poster was referring to it as a pretty, stylish top.

[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

This and make the sweater a cashmere in a beautiful jewel tone that flatters your coloring.
And a cool leather jacket.

[Anonymous]

I love that Quince sweater! I just ordered 3 of them (different colors).

I'm old, and I remember living through the Forenza sweater years. It's probably why I adore that sweater so much.

[Anonymous]

OP you need to come back afterwards and update us with what you wore and how it went.

Also, what is the rule of thirds?

[Anonymous]

That sequin top recommendation had to be a joke.

I agree that you should go with your favorite sweater and jeans combo. If you want to get something new, I think that monochromatic looks are closest to effortlessly cool.

Either casual: https://www.instagram.com/p/CWCSae6LdQM/ or a little fancier: https://www.brooklynblonde.com/2015/11/monochromatic-textures

[Anonymous]

Tbh I wouldn’t go but the clear answer is a sweater and some wide leg jeans and nothing, absolutely NOTHING, that suggests this was an event you in any way dressed up for, bought something new for, or overthought. Make sure your hair and makeup look good, keep the outfit simple, and say when you get there “I’ve only got 45 minutes til I have to leave for a prior engagement but it’s great to squeeze you in for a quick catch up!”

[Anonymous]

Anonymous wrote:Tbh I wouldn’t go but the clear answer is a sweater and some wide leg jeans and nothing, absolutely NOTHING, that suggests this was an event you in any way dressed up for, bought something new for, or overthought. Make sure your hair and makeup look good, keep the outfit simple, and say when you get there “I’ve only got 45 minutes til I have to leave for a prior engagement but it’s great to squeeze you in for a quick catch up!”

+1 Perfect.

[Anonymous]

Start your outfit with jeans, as long as they fit well, aren’t skinny, or overly distressed. A black, washed black, or medium blue, in a straight-leg silhouette with a high percentage of cotton compared to synthetic. Flares or a cropped bootcut could work and might help camouflage some extra weight, but your tailoring must be on point since they’ll look odd if not hemmed at exactly the right spot. A cotton straight leg is your safest bet.

On top, wear a beautiful cashmere or wool sweater in a color that’s flattering for you, which is probably not a neutral like black or ivory. Chunky knitwear with a shorter length is in, so stay away from any tunics so you don’t drown your waist. Fully tuck in the sweater or do a French tuck. Google videos on how to tuck in thick knitwear. You could also wear a silk shirt or sweater tank under a oversized wool blazer. If wearing a collared shirt, leave the collar inside the blazer instead of pulling it out. Tonal dressing could be chic here, like a dark green silk shirt under a jade blazer. Keep the color tone consistent in tonal dressing to keep your look harmonious (all cool tones, all warm, etc.).

Don’t wear a coat if you don’t need one. If it’s chilly, wear a leather jacket (slightly oversized, not tight) or a beautiful wool or cashmere coat in a flattering color.

For shoes, wear leather or suede mid-length boots with a square, western, or almond toe. Avoid boots that stop right at your ankle - they should go under your jeans. If wearing flares, go for a 70s style with a sky-high heel and platform to elongate your legs. Clean and condition your shoes.

If wearing a shirt and blazer on top, try an unstructured bag like a suede bucket or hobo. If wearing an oversized sweater, carry a more structured purse (think early 90s Coach leather bags with a top handle). Avoid all logos. Your purse and shoes are a good time to play around with color. For example, oxblood shoes and bag would look amazing with blue jeans and a ice blue sweater. Clean and condition your leather bag if it needs it.

Simple jewelry, nothing chunky or oversized. Clean it if you haven’t recently.

An interesting but not distracting belt to emphasize your waist. Your bag, belt, and shoes should look harmonious but not match exactly, unless they’re all black.

Don’t spend an extraordinary amount of time on your hair or makeup. Nothing would be more embarrassing than to have your friend comment or point out your appearance ( that would be the opposite of effortlessly cool). Do a face mask and keep your makeup simple. No overdone eyeshadow. Don’t get a blowout unless you are hopeless at styling your hair. If your hair is long, loose waves or a bouncy 90s blowout looks great. Google hair tutorial videos for inspiration and tips.

[Anonymous]

Anonymous wrote:Tbh I wouldn’t go but the clear answer is a sweater and some wide leg jeans and nothing, absolutely NOTHING, that suggests this was an event you in any way dressed up for, bought something new for, or overthought. Make sure your hair and makeup look good, keep the outfit simple, and say when you get there “I’ve only got 45 minutes til I have to leave for a prior engagement but it’s great to squeeze you in for a quick catch up!”

Yup. This is it right here. The focus needs to be on an “oh I can squeeze you in” moment.

[Anonymous]

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!

[Anonymous]

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.

No Rothy's unless you want to look like a mom at the playground in 2016, sorry!

[Anonymous]

Anonymous wrote:I love that Quince sweater! I just ordered 3 of them (different colors).

I'm old, and I remember living through the Forenza sweater years. It's probably why I adore that sweater so much.

I got this last year in white and I love love love it. It’s held up super well and I recently went back for a few more colors.

[Anonymous]

Anonymous wrote:

Anonymous wrote:Tbh I wouldn’t go but the clear answer is a sweater and some wide leg jeans and nothing, absolutely NOTHING, that suggests this was an event you in any way dressed up for, bought something new for, or overthought. Make sure your hair and makeup look good, keep the outfit simple, and say when you get there “I’ve only got 45 minutes til I have to leave for a prior engagement but it’s great to squeeze you in for a quick catch up!”

+1 Perfect.

Yep this!!

[Anonymous]

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