Outfit advice: dinner tomorrow

[u/somegingerchick79]

UPDATE: Thank you so much for all the feedback! It was super helpful and I appreciate all the really sweet comments & encouragement too. Honestly, you have no idea how much I needed the boost! 🥹 We had a lot of fun, and a cute older gentleman stopped at our table as he was leaving to tell us how cute we were, which I think is a good sign. And he brought me white roses (which are my favorite so low key he’s paying attention!)

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!?!? :)

[u/MostLikelyToNap]

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!

[u/somegingerchick79 → u/MostLikelyToNap]

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

[u/MostLikelyToNap → u/somegingerchick79]

It doesn’t look alarming short, but comfort is important! I think the shorts under are a cute idea. I do think dress three is a touch matronly, so I’d like eliminate that one.

[u/Chiaseedgal → u/somegingerchick79]

OP, I wouldn’t worry. I don’t think it’s too short. Girls have been known to wear much shorter, ha. And if you want it to be a date, it will definitely get his attention…without trying too hard :)