What To Wear-Date Night in November.

I think as parents, we need to get out a little don’t you agree?

Date nights are rare around here since the kiddo came along, but we made a pact that we would at least do date nights once a month. Still waiting for this ritual event to take place. I guess it would be a good New Year’s Resolution (gosh is it really almost that time again!?). My birthday is coming up  in about a month though so I am trying to wrap my head around where I want to go to celebrate. There are so many options in Chicago that it’s hard to choose just one!

I have put together an outfit that you can pull off for your date nights. Single? Yes, you can pull this off too and it is a great first-impression outfit . This is my go to look that has some glam without all the fuss that I have managed to pull off many times.



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I have pulled a graphic tunic tee (3) into the mix because I think it gives the outfit some life to it. This is only my second time making inspiration boards and I closed the browser that had the tee on it so I can’t find it now for the life of me. I apologize for that!  Any graphic tunic tee will do and there are many options. If you want to tone the shirt down a bit, be my guest, it will work as well. I do this myself.

Also, a clutch purse of some sort with a pop of color helps pull the outfit together.  And you can’t go wrong with a black flat boot that can take you from catching a flick to grabbing cocktails to trying that new Sushi spot downtown.

And if you tell me you can’t pull off skinny jeans I will come over there and shake you and say “what’s wrong with you!” Yes you can! It’s all about balancing it out on top. As long as the top is long enough, you are good to go, trust me. If I still can’t convince you, denim leggings are an excellent alternative that are so versatile and comfortable,without looking like you just rolled out of bed.

So do you think you can pull this outfit off? (nod and say yes 🙂 ). Where do you think you would wear this on your date night? I’d love to hear your ideas!

And just fyi-I am not being paid to promote these particular items nor are there affiliate links. I just really dig these outfit ideas and wanted to share them with you. All opinions in this post are my own.


  1. Deanna, you are adorable! I love your writing style. It feels like you are just chatting with girlfriends. Now I’m going to do a little online shopping for some great flat boots. Thanks for the inspiration!
    Mo at Mocadeaux recently posted…Pizza And Wine – A Perfect CombinationMy Profile

  2. Haha Thanks Mo! I enjoyed writing this too, I can’t wait to do more of these!

    I love this look and pull it off in many types of dates with the hubs and scenarios. And a flat boot is a must! You must post a pic when you find a pair! I think it’s an outfit that is pretty universal that anyone can pull off!
    Chi City Mom recently posted…What To Wear-Date Night in November.My Profile

  3. Hello Deanna ! I enjoyed reading this post. I liked your writing style. It felt like we were having this conversation face to face. Advance Happy B’Day girl. My birthday is also in December. ( We have something in common ) I like the outfit, would like to try it out in one of my outings.
    Divya recently posted…R in A- Z Photography ChallengeMy Profile

    • Chi City Mom says:

      Thank You! That means so much to me. Still trying to figure out a lot of things, but the writing style at least I got going on 🙂

      So you are a fellow Sag too! That is great. Definitely try the outfit on and let me know where you wore it to your outings!