Picture this: You meet a guy at a friend’s party and have a brief conversation, where the two of you really hit it off. The following week, said guy asks you out to dinner and you immediately say yes. He is thrilled by your response and tells you when he will pick you up. However, (and here is the tricky part) he neglected to provide any details of the date. Because you have only had one short conversation with this guy, you do not want to pester him with questions of what to bring, where the two of you are going, and most importantly, what to wear! Sound familiar to any of you?
I experienced this exact situation recently. Being the fashion lover that I am, choosing the appropriate outfit for the night was the only thing I was worried about. There is a fine line between being overdressed and being underdressed, and I was walking it. Keeping that in mind, I wanted to be comfortable and confident, while also giving this guy a good impression of me.
About a dozen wardrobe changes later, I decided on an outfit that ended up being perfect for the occasion. I am confident that at some point in time, many of you will experience this same dilemma. Fear not! Here are some of my foolproof wardrobe recommendations, perfect for most any event. First dates can be stressful, so nailing the outfit gives you one less thing to worry about so that you have an enjoyable (and fashionable) night.
Look # 1 LBB + Jean Jacket
This look is perfect because we’ve all got these things stashed in our closets. Pair your little black dress with a jean jacket and a pair of cute (but not flashy) flats. Take a larger bag with you so that if a jean jacket is too casual for the date, you can stash it in your purse. You can also keep a necklace in your bag in case you need to dress up the look. Piece of cake!
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Look # 2 Blazer + Dark Skinny Jeans + Boots
This look is so versatile, and one of my favorites. Throw on your favorite pair of dark wash skinny jeans with a flat boot. (I prefer riding boots with this outfit.) Try to avoid jeans so dark that they appear black—you don’t want to look like you’re wearing leggings. Pair this with your favorite blazer and a cute blouse.
This outfit works because you have the casual aspect of the jeans and boots, but it also appears dressy from the dark wash of the jeans and the blazer. Keep the jewelry simple with this look. Finally, opt for a small bag with a long shoulder strap. If the date ends up being casual, the purse can act as a crossbody bag. If the date is a bit more formal, just tuck the strap into the bag—instant clutch!
Look # 3 Trouser Jeans + Leather Jacket
It’s hard to go wrong with a good pair of trouser jeans—dressy, yet comfortable. Pair these bottoms with a fun, printed blouse. Top it all off with a tailored leather jacket. It will add a little edge to the ensemble without going overboard. If you discover that the jacket is too casual, all you have to do it take it off and reveal your feminine shirt. No sweat.
I like pairing this look with a flat that has a subtle, contrasting pattern. It adds some pizazz to the outfit, but because the patterns are of the same color scheme, it’s not too busy. Some bangles and a colorful clutch complete this look.
Flashy jewelry and stilettos have a place, and it’s not a first date (unless you’re going to a rock concert). Gaudy accessories, and even makeup, are distracting and your date will be more focused on your clanking bangles than the conversation you are having. Here’s the bottom line: The key to nailing any outfit on a first date, is to keep it simple. While I’m a huge advocate of a fashion-forward ensemble, at the end of the night, you want your date to remember you more than whatever you’re wearing.