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

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

Jessica Alexander Photography

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