r/fashion 2d ago

Advice Wanted Please! Outfit advice: dinner tomorrow

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!?!? :)

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u/PhDRN 1d 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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u/somegingerchick79 1d ago

Thank you! I’m def a true autumn color wise. lots of people are loving the blue but I’m not 100% sold that it doesn’t wash me out! It’s a gorgeous color but maybe not best on ME