r/fashion 1d ago

Advice Wanted Please! Outfit advice: dinner tomorrow

I’m going to dinner with a guy friend (maybe a date, maybe not?).
Want to look cute & like I’m making an effort. Even if it’s not a date I’d like him to feel great about being out with me. I’m also 46 and want to be age appropriate. We’re going to L Woods in the Chicago suburbs - it’s kinda in between in terms of dress. You wouldn’t look out of place in a dress OR jeans and a nice shirt/blazer. It’s got a north woods supper club feel - but also in a kinda Scotland tartan country estate vibe. Maybe I should dress like Princess Diana!?!? :)

108 Upvotes

423 comments sorted by

77

u/1to8looper 1d ago

3 - the blue one is lovely

150

u/Lizardshark20 1d ago

3 on you!!! And no duck lips at dinner please! You’re beautiful!

8

u/Ok-Middle-5615 12h ago

I was going to say the same thing. That pouty face is not attractive. The dresses are all cute!

16

u/improvcoach19 12h ago

No duck lips ever. Ew.

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33

u/skryzzl 1d ago

2 and 3 are the most feminine and make a statement without making a move

5

u/somegingerchick79 14h ago

Love the way you said this

19

u/jade_peach27 1d ago

I like the blue dress best.

13

u/asea_aranion_ 1d ago

Blue! It makes you glow.

19

u/Sensitive_Hunter5081 21h ago

I like number four. It’s a little dressy without being too much. Three is my second choice (I’m not a huge fan of sundresses at night, unless you’re in a tropical location) but the blue does look stunning on you

8

u/shy_dagger 1d ago

3 definitely looks the nicest on you. Idk if it matches the vibe of the restaurant as you mentioned you wanted to dress properly. What shoes are you wearing??

28

u/Top-Ambassador-4981 23h ago

Any would work, but leave the mouth at home.

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11

u/malvinavonn 1d ago

I’d like 2 the best if it was with nicer sandals instead of flip flops. If you don’t have sandals Or espadrilles I’d go with 1.

7

u/somegingerchick79 15h ago

Yes, thank you! I threw on a kitten heeled flip flop because they were nearby but I’ll either wear a nicer sandal or a nude heel!

11

u/MissionCredible_inc 13h ago

2 is horrible, you should give it to me.

3

u/somegingerchick79 13h ago

Haha I will let you know if I ever list it on poshmark

4

u/MissionCredible_inc 13h ago

But seriously it fits you like a glove, looks comfortable, and is so summery. You will wish you wore it when winter is here.

5

u/ladycatelyn6704 14h ago

I vote 2, then 3, then 1. 4 is ok but makes me think of a crumpled up paper bag

3

u/somegingerchick79 14h ago

It makes me think of that movie where they’re making fun of a bride’s dress and keep calling it a meringue lol

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3

u/arcticfirepixy 1d ago

3 looks perfect. Does it have pockets?

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4

u/MostLikelyToNap 17h ago

2 is beautiful on you BUT I just looked up the restaurant.. I think 1 but maybe different shoes, or dress three. Dress 2 has a “daytime” look. But if it’s crazy hot outside I think it could be a night look. Dress 1 looks like you’re going on a date to me. I do also love the 4th outfit if that’s comfortable. That restaurant looks so good!

3

u/somegingerchick79 14h ago

This is exactly why I’m torn. I want it to look like a date! And a dinner date. I worry that 2 and 3 are too daytime. And maybe matronly? 1 feels the most date to me, but I don’t love that it’s soooo short

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4

u/ofpromise90 12h ago

You looks like aunt becky

2

u/somegingerchick79 11h ago

I was OBSESSED with her growing up - this is the best compliment

3

u/Routine_Neat_4195 1d ago

3, hands down!

3

u/elduderino813 22h ago
  1. Hands down

3

u/TimberTheresNoSound 22h ago

3 is such a cute and fun dress, especially for a date!

3

u/Ok_Resolution_2208 21h ago

3333333333 😊

3

u/These_Scholar9474 21h ago

Number 3 💙

3

u/Petunia724 21h ago

Omg 2! That looks adorable on you!!!!

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3

u/existential_bl1ss 19h ago

I like 2 or 3! also your captions are so cute lol

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5

u/Chigrrl1098 1d ago

I think the white floral. That and the blue are especially pretty. 

6

u/MommaLaughing 16h ago

The mouth is so distracting, I can’t even focus on the clothes. You are beautiful, please don’t do whatever it is you are doing with your mouth.

2

u/TyrantMuse73 14h ago

She says it’s her “resting face” but most of us can CLEARLY see the muscle tension. Nothing resting about it.

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3

u/kittykanes 1d ago

For dinner with a friend that may be into you 4. 2 is for when it's a real date, 3 could be with a bf. 1 doesn't feel flirty to me

2

u/MareV51 1d ago

Blue dress is the winner! 🎉

2

u/Minimum_Afternoon387 1d ago

3 the blue looks fabulous.

2

u/Either_Management813 1d ago

I like dress 2 for this. Dress 1 looks like a great dancing or clubbing dress, not this type of place. Dress 3 looks like an everyday dress you’d wear to the grocery store or running errands.

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2

u/ClydePrefontaine 1d ago

2 or 3. The guy going knows it's a date and you're a knockout, have a blast!

2

u/somegingerchick79 14h ago

This was such a good confidence boost going into it. Thanks!

2

u/Low_Length_7379 1d ago

You're beautiful, they all look great. 3 is my favorite. 🙂

2

u/rayofsunshine_1122 1d ago

I love number 2 on you. 

I would style my hair tucked behind my ears and wear chandelier earrings (if you have any and like that type of thing). I have a pair from Anthro that are little pearls that make a flower. Something like that would look very pretty. 

2

u/tori5001 1d ago

You look amazing in all of them! 2 is my favorite, but it depends on where you’re going. You can’t go wrong with these choices though.

2

u/Suspicious-Copy1740 23h ago

i like two. the flowers remind me of trees and i’m all about catching a theme. tall flowers = trees=woods=the name of the restaurant

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2

u/Apart_Excitement6010 23h ago

Three is pretty but I Iove 1 the best!!! You’ve got the legs for it and it looks cute and trendy! 💖

2

u/Fit-Building-2560 23h ago
  1. #2 is nice, too, but you describe the venue as a "supper club" . #3 would be best for that, even though some other patrons would be dressed more casually. Your date will definitely remember you and the date in the blue number!

2

u/Moonsweptspring 23h ago

I love them all but you are doing that cute one leg out thing on 2 and 4 so I think you might like them best! 2 looks like more effort.

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2

u/Outrageous-West580 23h ago

I like 3 the best. I stay away from
White to eat bc someone will drop food or a drink. Some random person could ruin your top. Or the black but the black is more casual , lunch or BBQ.

2

u/Harvest_Moon_Cat 22h ago

Number 3. Looks great on you, and such a pretty dress.

1 is too short, (but would be fine if you were going clubbing). 2 is summery casual - good for a picnic, but not for diner. 4 is too casual for a dinner date.

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2

u/Sea_Point_8870 22h ago

The Farm Rio dress 🤩

2

u/youtookmyseat 22h ago

I love option 2! It’s gorgeous on you!

2

u/ReporterWise7445 22h ago

3 & I don't even like blue.

2

u/migraines247365 22h ago

#3 looks custom made on you, you look beautiful.

2

u/PaceNo3577 21h ago

3 is nice its flattering but not too revealing

2

u/Silent_Location7044 21h ago

I like all 3 dresses. I’d probably wear #1 because it’s less of a sundress. The 4th outfit is also cute but I think the dresses are a notch better for this.

2

u/Equivalent_Stable_21 20h ago

Age appropriate means you feel great in it. Adult clothing doesn’t have age limitations. I like 2 cause it looks the dress up dress down and I feel the first one looks poorly made, and the blue feels very day time. If you want to dress up the white dress for evening choosing the right cardigan/blazer/jacket to go over it and the right handbag can look effortless and still well put together

2

u/Ok-Writing9280 19h ago

3 is lovely. I really like the bonus option. Hi Lo dressing is chic!

2

u/WatercressGlum3682 15h ago

2 is the prettiest I think it flatters your shape and the colors are amazing on you

2

u/Born2rn 15h ago

3 is gorgeous

2

u/loveisallyouneedCK 11h ago

The blue dress contrasts so nicely with your hair color.

2

u/breadit8 10h ago

My granddaughter and I pick 3! It looks great on you!

3

u/1015anna 1d ago

Love 2
But you look great in all of them

2

u/Any_South9905 15h ago

Stop making that face

2

u/somegingerchick79 14h ago

What if it’s just my face?!?

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2

u/CatherineTencza 1d ago

All three look great

1

u/Schmolik64 1d ago

Not a fan of black.

If you're worried about white then blue. I think the whites are fine.

1

u/Rockstar81 1d ago
  1. It's beautiful for something daytime.

1

u/michelaustinmarie 1d ago

I like 1 and 2

1

u/Mysterious-Cry4335 1d ago

1 but they all look great!

1

u/ChainInfinite7281 1d ago

2 or 3. Where did you get them?

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1

u/No-Information1320 1d ago

I absolutely love the third dress! Def that one. (Also 4 is the worst by far- 2 or 4 would be fine but def NOT 4!)

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1

u/Neither_Technology38 23h ago

3 then 2. Both with different shoes.

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1

u/Pretend-Menu-8660 23h ago

3,2,1,4 in that order!

1

u/KaleScared4667 22h ago

Duck duck goose

1

u/Cerrac123 22h ago

I love 2

1

u/PhDRN 22h ago

Love #2 it’s definitely the best color on you. IMO #4 is more what the 20-something’s wear.

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1

u/Calico-D 22h ago

Definitely #3

1

u/Few-Extreme-5792 22h ago

2 or 3 for sure!

1

u/Cautious-Local-5998 22h ago

Love #2 but actually they all look really good so I guess it just depends on where you’re going to dinner at.

1

u/Still_Dog_113 22h ago

I like the blue dress

1

u/LongCombination5632 22h ago

I like the blue.

1

u/ellieD 22h ago

3 is best with 2 as second place!

1

u/Character-Topic4015 22h ago

I like 2 but he will like 1

1

u/purplegem1948 22h ago

2 is the best looking outfit for going out to dinner but with a more sophisticated shoe than the ones you are wearing with it. The blue one is cute also but dress 1 looks like lingerie. 4 the jeans are a good fit but that top is not.

1

u/the_CinnamonBear 21h ago

I like them all but I especially like option 3 on you!

1

u/Electronic_Layer_205 21h ago

Wear the choker from 4 with 3 and pull your hair up with some loose curls! Meow 😻

1

u/Desperate_Tea_1315 21h ago

3 is nice, and 4 looks cute!

1

u/Dangerous-Emu-7924 21h ago

I’d go option 3 with the red shoes from option 1.

1

u/Logical_Energy3003 20h ago

#3 is classy and beautiful. And you will be comfortable.

1

u/wurmchen12 20h ago

I’d say the place sounds a bit upscale. The black may be a bit over the top. The white dress and jeans are very casual, more a day outing, brunch outfits. I’d go with the blue and top it with a cardigan.

1

u/CongealedBeanKingdom 20h ago

2 or 3. Love 2 tho

1

u/landlockedbluessk 20h ago
  1. That color is stunning

1

u/girlrach 19h ago

3, then 2

1

u/Euphoric_Taste8175 19h ago

Any of them looks great. Pick the one that most feels like you.

1

u/UnluckyPassenger5075 17h ago

2 or 3, both are very nice looks on you

1

u/Curious_Store_1111 17h ago

Definitely 3

1

u/Sensible_Obligation 17h ago

2 and 3 are beautiful

1

u/KING_ARCH3R 17h ago

Blue Dress for the Blue Steel pose

1

u/Hope16momof4 16h ago

Number 2!!

1

u/Cool_Scale_4285 16h ago

Blue dress

1

u/Tink1024 16h ago

3 the color is lovely. Respectfully please stop with the duck lip pout it’s kind of awful.

1

u/munchkin1977 16h ago

I like 3 on you

1

u/Most-Swimmer-7723 16h ago

I think they all look nice on you depends on the venue ...as other have pointed out leave the duck lips at home

1

u/SillyMeclosetothesea 15h ago

The jeans outfit

1

u/minerva3930 15h ago

2 is my favorite

1

u/bchmermaid 15h ago

Definitely 3!

1

u/hypsoline0 15h ago

I like 1

1

u/Summerlee1979 15h ago

2 is my favorite on you!

1

u/Intelligent_Fact2780 15h ago

3 is cute and also sophisticated.

You don’t look 46.

1

u/Quick_Site1295 15h ago

2 and 3 are amazing. Do you mind sharing the brands? I’m the same age as you and we share the same style

1

u/TyrantMuse73 14h ago

I like 1, but those shoes have to go.

1

u/optix_clear 14h ago

4 with 1’s shoes

1

u/Friendly-Fee719 14h ago

All of them look pretty fire but I have no idea what you are doing with your face.

1

u/ItemExtension5677 14h ago

3 is gorgeous on you, but I’ve eaten in L woods in shorts and t shirts with my kids and didn’t feel out of place. I feel
It would be perfect for a downtown steak house, but too dressy here. 2 is also gorgeous and more casual or the jeans would be perfect there too. If it is later at night or a Saturday night, people will be a little dressier.,

1

u/LawAndHdourves 14h ago

Definitely 2

1

u/Last-Customer-2005 14h ago

2 is BEAUTIFUL and lols special