The Best Cold Weather Date Night Outfit

all black date night look

ASOS Balloon Sleeve Sweater / Madewell High-Rise Slim Boy Jean in Lunar Wash / Sam Edelman Hazel Pointy Toe Pumps in Black Suede / Everlane Day Tote Mini / Ray-Ban Original Aviator / Daniel Wellington Classic Petite Mesh Watch in Rose Gold

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When Chris and I first started dating, our schedules were busy, we lived +/- 30 minutes apart, and we’d mostly only see each other on the weekends and we quickly realized that one date night during the week was crucial to our relationship. We started to make date night once a week (typically Thursday’s) a priority to help break up the week and spend some one-on-one time, away from our roommates. 

Now that we live together, a majority of our date nights are spent at home, cooking dinner together, opening a bottle of wine, and watching a movie we’ve been dying to see. We do try to get out a few times a month for date night – seeing a movie, grabbing dinner, trying a new place for drinks – but once the cold temperatures roll around, the last thing I want to do is leave our apartment and freeze my ass off.

Enter the chicest black sweater, that’s under $40.

If I can put together an outfit that looks chic and keeps my cozy, I’m all for it. Especially for date night.

Paired with a light-washed pair of black jeans and a great pair of black pumps, I can stay warm and still look put together for date night! I actually even wore this outfit, paired with my faux fur leopard coat (under $100!), for New Year’s Eve dinner. The fit of these Madewell jeans is so good, too. Tight where you want them to be, lose to fit all the date night food and drinks, and a killer wash. I loved them so much, I also picked them up in a light wash. 

What’s your favorite date night outfit during the winter months?

Shop The Post

ASOS Balloon Sleeve Sweater / Madewell High-Rise Slim Boy Jean in Lunar Wash / Sam Edelman Hazel Pointy Toe Pumps in Black Suede / Everlane Day Tote Mini / Ray-Ban Original Aviator / Daniel Wellington Classic Petite Mesh Watch in Rose Gold

Photography By: Caroline The Photographer

Leave a Reply


  1. 2.3.20
    Rach said:

    Love this all black outfit! Super cute and now you are inspiring me to re-create this look!

    • 3.2.20
      Rachel said:

      Thanks Rach! Can’t wait to see you rocking it!

  2. 2.3.20
    rebecca said:

    YES GIRL!!!! killing it in the all black. my date night outfit is similar except with some heeled booties instead of pumps!

    xx rebecca //

    • 3.2.20
      Rachel said:


  3. 2.3.20
    Mariah said:

    I always struggle looking cute when its cold. My booties I wear year round because I hate having my feet cold. I definitely think shoes can make an outfit feel nicer or dressed down.


    • 3.2.20
      Rachel said:

      Getting out during the winter is the worst, right? Nothing a chunky sweater can’t fix 😉

  4. 2.3.20
    Stephanie Whitman said:

    This is so my kinda outfit for date night. I love the monochromatic black look. SO chic, for sure! Usually I just opt for skinnies, a chunky sweater, and booties on date night. My hubs is super casual so I try to stay that way as much as possible too!

    • 3.2.20
      Rachel said:

      I can totally picture you rocking this! All-black is my fav!

  5. 2.3.20
    Radi said:

    Love this look and the pumps for date night!

    • 3.2.20
      Rachel said:

      Thank you!

  6. 2.4.20
    Lizzie said:

    This outfit looks so chic! I love this all black ensemble, especially those heels!


    • 3.2.20
      Rachel said:

      Thanks Lizzie!

  7. 2.4.20
    Laura Leigh said:

    I am obsessed with this look and this backdrop! Pure perfection – great planning lady!

    xo Laura Leigh

    • 3.2.20
      Rachel said:

      Thanks, girl! I’m obsessed with Newburyport and was so excited to shoot on the cute streets!

  8. 2.4.20

    I am LOVING where you took these photos! You look gorgeous, I love the open hem on the jeans.

    • 3.2.20
      Rachel said:

      Isn’t the dark building gorgeous!?

  9. 2.4.20
    Greta said:

    I love a good all black look, especially for date night! You look so good girl!

    • 3.2.20
      Rachel said:

      Thanks Greta!

  10. 2.4.20

    Love this classic look! Black pumps are also my favorite date night shoe 🙂

    -xo, Azanique |

    • 3.2.20
      Rachel said:

      Thanks Azanique!

  11. 2.5.20

    Coming from New York, I appreciate the all black everything outfit! Love how you styled the pieces! xoxo, Sarah

    • 3.2.20
      Rachel said:

      Yasss! All black is the way to go!

  12. 2.5.20
    Anna English said:

    I love the simplicity of this look and how it can easily be recreated with pieces I already own!

    • 3.2.20
      Rachel said:

      Thanks Anna!

  13. 2.10.20
    Kristina said:

    Can’t go wrong with a monochrome look and your hair looks so good!

    • 3.2.20
      Rachel said:

      Aw thanks! I’m such a sucker for an all-black look!