With Love
From Kat

With Love
From Kat

What to Wear on Date Night

Venice, CA

I always get a ton of questions about what to wear on a first date or date in general!  I love wearing a midi dress, with a simple heel and small clutch/bag on a date night.  It’s feminine and elegant, but also effortless and comfortable.  You never want to try too hard…or show too much skin!  Leave something to the imagination ;)  Plus a midi dress can easily fit in anywhere from a casual bar to a more upscale hotel lounge, speakeasy, event, or formal dinner.  You never know where the night will take you so you want to make sure you dress the part.

I always get so many questions about my favorite dress brands.

Honestly, I love Topshop, Mango, ALC, L’Academie, Misa, and Reformation.  These brands all consistently fit well, are high quality, and last for years and years.  I’m willing to splurge on a beautiful dress if I know I’m going to get a bang for my buck and be able to wear it countless different ways with a leather jacket, button down shirt, vest, trench, or blazer!

In terms of these Stuart Weitzman heels that I always wear…yes they are 100% worth it and yes they are comfortable.  I own them in 7 different colors – that’s how much I love them.  They make your feet look so long and thin and your legs look super lean!  I’m not into fussy shoes and these are perfect for every and any occasion.

There are several different style variations of these sandals but I prefer the Nudistong because they’re high (almost 4″), but not insanely high to the point of being kind of painful like the 110mm Nudist style.  Which by the way, do make your legs look absolutely killer and amazing, but they just hurt!  As far as an everyday heel style that I’m obsessed with and that many of you have seen me wear a million times…I love the NearlyNude which is about a 3″ heel.  I can walk for hours in these which is especially great if you’re into whoever you’re on a date with ;)

Shop all of my date night must haves below including what bra I love wearing under silk dresses, and what mascara, highlighter and bronzer I swear by!

What to Wear on Date Night




Shop the Post
ALC dress (also love this one)  |  Stuart Weitzman heels
Chloe bag  |  Boardwalk sunnies (similar)

Jessica Alexander Photography

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  • Simplement Lui says:

    A beautiful dress for a very nice and elegant outfit! Happy Monday xx


    August 13, 2018 | Reply
  • Cristina - Memories of the Pacific says:

    That dress you are wearing is so beautiful, Kat!
    I love how legs look with heels but I just can’t be bothered…they always hurt my feet so I go for wedges instead.

    August 13, 2018 | Reply
  • Ray Amaari says:

    Such a fabulous look.


    August 13, 2018 | Reply
  • Roses for Fridays | by mia says:
    August 13, 2018 | Reply
  • Rach says:

    This dress is definitely a perfect date night outfit!It’s so flirty but still classy!


    August 13, 2018 | Reply
  • Rin Longo says:

    This dress is so flattering on you! Love the floral and ruffle details.

    xoxo, Rin
    Ramblings with Rin

    August 13, 2018 | Reply
  • Coco B. @ Millennielle says:

    LOVE that dress Kat!

    August 13, 2018 | Reply
  • Inna says:

    What a cute outfit!


    August 13, 2018 | Reply
  • Dana says:

    Oh my, this dress is GORGEOUS! Love it for date night!

    The Champagne Edit

    August 13, 2018 | Reply
  • Claire V says:

    Such a classy/sexy look – this is what I absolutely love about you and the content you post that sets you apart from other bloggers. So effortlessly sexy, yet classy, and chic altogether!

    August 13, 2018 | Reply
  • My lovely people says:

    This dress is really beautiful and the heels are amazing. You look gorgeous

    New blog post: my two combinations with a white linen jumpsuits. Don’t miss it!!!!!

    Kisses from Miami


    August 14, 2018 | Reply
  • Lisa Autumn says:

    This dress looks beautiful on you! Obsessed!

    x Lisa | lisaautumn.com

    August 14, 2018 | Reply
  • May says:

    Love the dress and the shoes! Definitely great for a date night.

    May || http://themoderness.com

    August 15, 2018 | Reply
  • Jessica from What To Style says:

    You look gorgeous in this dress and its color suits you so well! Fortunately, I have a very similar bag to yours! ❤

    Jessica | New post: whattostyle.blogspot.com |
    Instagram @ what_to_style

    August 15, 2018 | Reply
  • Delaine says:

    That dress is fire, I absolutely love it but that price tag though is ridiculous, yes it is gorgeous but wow. You rocked though.


    August 15, 2018 | Reply
  • Amelie says:

    Yes I agree this is a perfect date night dress and has a nice refreshing summer feel and colours. beautiful pictures.

    August 16, 2018 | Reply
  • Jae says:

    Such a great dress! I love the floral print on black with that pop of white!

    August 17, 2018 | Reply
  • Fashionandcash says:

    I love this look

    August 17, 2018 | Reply
  • Cozy Teddy Coat - With Love From Kat | Lifestyle Blog says:

    […] size down if you want to wear thin socks and have narrow feet. These boots are going to be an ideal date night heel in the rain/snow since I won’t have to worry about beating them […]

    November 25, 2019 | Reply