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When it comes to dating it can be tricky trying to find the right outfit. What you wear depends on what type of date you are going on; is it the first time you are meeting each other or are you in a relationship, and what day of the week it is on really matters what you are going to wear on the date. In the summer when I go on dates I always opt for a dress. I not only feel the most confident in dresses, but a dress can be tailored to any type of date situation. During the winter is when my date night wardrobe becomes a little tricker, and quite frankly, I am bored of. For date nights I have a handful of tops that I rotate through, but lately, I have been looking to freshen up my date night looks with a new top or two.