Foolproof Date Night Looks

So let’s be real we all want to be that girl who shows up to her date looking effortlessly chic like she just rolled out of bed looking this way.  But let’s check back into reality, it probably takes us about an hour to achieve that “cool girl” look.  I’m happy to tell you that with my help, looking chic for date night will in fact be effortless.  Although I do recommend a shower, you could technically roll out of a bed and throw on any of these foolproof date night outfits and look and feel amazing!

Let’s start with high waisted wide-leg pants.  This is one of my favorite pieces to style my client’s in because it gives women a sexy hourglass shape by defining your waist.  Not to mention once you pair these pants with a pair of heels your legs will look miles long.  On the top, I like to style these pants with a tight bodysuit or tucked in silk cami.  

Photo Credit: &, Top: Cami NYC, Pants: Halogen, Shoes: Stuart Weitzman, Earrings: Nordstrom, Clutch: Nordstrom

We all knew I was going to mention a little black dress because what woman doesn’t feel sexy and confident in their go-to dress?  Let’s put a modern twist on this look and pair it with a black duster and a great pair of heels.  Just like that you’ve made your traditional date night look more trendy and effortless.  Pairing a sexy fitted piece of clothing with an oversized casual piece instantly creates that cool-girl look that we’re looking for.

Photo Credit: &, Duster: Babaton, Dress: Susana Monaco, Heels: Steve Madden, Earrings: Petit Moments, Clutch: Kayu

The last go-to outfit choice I have for your date night involves a sexy pair of black skinny jeans.  As we just did with the typical date night dress, let’s give this skinny jean outfit a modern twist.  Grab a pair of heeled over the knee boots and a silky one-shouldered blouse and you’re looking fab!  The combo of an over the knee heeled boot and your skinny jeans will elongate your legs and draw the eye up.  The reason why I love a silky one-shouldered blouse is that it’s the perfect mix of feminine and sexy.  I personally think that showing off your clavicle is a subtle and simple way to look classy and sexy.

Photo Credit:,, &, Top: Intermix, Jeans: Frame, Boots: Villa Rouge, Belt: Lizzie Fortunato, Earrings: Isabel Marant, Clutch: Tamara Mellon

So now that we have your effortless cool-girl looks ready for date night, we have to address your confidence.  Above all if you don’t feel confident the second you walk out of the door, your date night will flop.  Fashion is my favorite way to boost confidence.  If you feel beautiful and amazing in what you’re wearing, forget the rules and wear it!  Luckily with the date night looks, I’ve styled above, you’ll never have to second guess your outfit again. 

Written by: Caitlin Jaymes

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