Date Night outfits can be as casual and as fancy as you want it. I for example always need to take into account the weather and location of the date. No one is going to wear a miniskirt to a rock climbing date haha.
I went downtown Santa Barbara to "Blue Water Grill" which overlook the pacific coast. This location has outdoor seating and luckily my date gave me a warning that we would be sitting outside.
This outfit is actually very simple once it is broken down. I start off by going with a neutral skirt with a plain black blouse. I knew the black blouse would be perfect with the black knee high boots. The leather jacket is also a darker neutral shade, matching the skirt. The necklace is from World Market and my glasses are from H&M. All together this made up this super chic comfortable outfit. If you are ever worried about to wear to a date you can never go wrong with basics and just add accessories to them to dress up the look more.
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