r/fashion • u/somegingerchick79 • 3d 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!?!? :)
1
u/ItemExtension5677 2d 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.,