The One Question to Ask Yourself Before Dressing for Any Occasion

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It’s that time of year again, party after party after party. And not just with your nearest and dearest friends and family, but with your coworkers, bosses, and more distant (and sometimes more judgmental) relatives. I don’t know about you, but these kinds of events give me serious anxiety, usually because I have little to no context as to what to expect, especially about what to wear. Even if I am told what to expect, “Just dress casually!” I still have a million more questions; what if their idea of casual is my idea of dressed up? Like, “casual” as in yoga pants and a hoodie or “casual” as in jeans and a real top with buttons and stuff?

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After some time of stressing and worrying about what to wear, I developed a question to help guide my clothing choices to find an outfit I can feel comfortable and confident in. The question could be asked before picking something out or applied to an outfit idea you already have in mind. The question is this: What would I be comfortable in this if other guests were really dressed up and if others guests were dressed down?

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The sweet spot is choosing an outfit right in the middle. I know this sounds impossible, but once you think of the event in this perspective, you start to realize that there can be a happy medium. So, if you have no context to the event, think of an outfit fancy enough to fit in with a dressed up crowd but casual enough if guests showed up in jeans and a tee shirt. The same method can be applied to a designated “dressy” event, because there are hundreds of options in this scenario too. You can show up in a elegant top and dark wash jeans or a full-length gown. If you ask yourself the aforementioned question and still feel comfortable in one of those options, great! If not, perhaps a cocktail dress is the perfect compromise.


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In all honesty, most of the time there is a mixture of people in their Sunday’s Best and others who wore the same sneakers that they walked the dog in earlier that day. But if you take this situation into account, you dress to feel confident no matter what the anyone else is wearing. And there’s no better feeling than being comfortable in your own skin. So, party on, people!


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Is This “Dirty Word” a Do or a Don’t?

finished sandalsEven if you are only slightly obsessed with Anna Wintour and have a internet connection, you have probably seen that she considers the word “trend” a “dirty word.” Which seems like somewhat of a hypocritical statement; Anna Wintour being the Editor-in-Chief of a magazine that is practically the birthplace of trends. However, the queen of fashion (all hail Anna!) makes this statement because she believes fashion is about an individual’s character, not what’s “in” and that everyone should wear it.

I absolutely embrace this belief of individual style being the ultimate goal instead of owning the “newest” or “trendiest” clothes. But with that being said, you are bound to be wearing “trends” if you meant to or not. So, if you can’t escape trends (if you did you would have to buy new un-trendy clothes every month, which isn’t that just as bad a buying trendy clothes every month?), how do you pick what trends are right for you?

Trends are easy traps to fall into; they are new and exciting. It’s very simple to feel a “love at first sight” kind of moment with a trend, only to find a few months later seeing that trendy item again makes you say to yourself, “what was I thinking?!” The best way to avoid this, is to really get to know you. What you like, what you feel comfortable in, what you want to say to the world. When you have a better sense of yourself, it’s easy to tell if a “trendy” item is just a fading fad or will become a part of your signature style. You have to see yourself wearing it long after it’s trendy days are over, and not feel like a fool or outdated.

If you read my last post, I spoke about wanting to embrace the sunny yellow and pastel pink trend; because these are some of my favorite colors to see and wear. Since I already love these colors, I’ll continue to wear them. In the opposite case, such as the bohemian, “Coachella,” trend that’s been going strong for a few years now, I just can’t get into it. Trust me, I tried flowy tops and fringe-everything, and looked the part because that’s what was “in.” But I easily tire of these things instead of getting excited to wear them. Therefore, I am left with the I-have-nothing-to-wear dilemma.

So though there are countless of other colors and trends this upcoming season, these flowery shades are the ones that really speak to me. It’s important to pick and choose the trends that you like best/work best for you, if any at all! And if you can’t or don’t want to participate in a trend, that’s okay too (even preferable to the most influential tastemakers).