Despite my love of fashion, I sometimes find myself struggling to pick out outfits for certain occasions. I’ve stressed over what to wear on an interview or to a wedding. I’ve obsessively scrolled through Instagram ahead of beach vacations, hoping to feel inspired before I start packing. I even have the same fashion struggle year after year: finding a jacket that will actually look OK when paired with my Halloween costume (and yes, I’ve already started thinking about it — in July).
Still, there’s one occasion that doesn’t exactly send me into that well-known, what-the-heck-do-wear type spiral, and that, my friends, is called date night.
It's not that I’m exceptionally skilled at picking out dresses fit for fancy restaurants, or that I’ve found a comfy-cute pairing that always works for a boardwalk stroll. It doesn't even matter that I'm in a long-term relationship and, at this point, have worn some truly hideous things around my significant other. It's that I don’t understand what, exactly, turns a "date night" into its own huge event — or at least, one that requires a billion articles filled with outfit suggestions.
To me, there’s isn’t much of a difference between going out for drinks with my boyfriend and going out for drinks with friends. In both cases, I might reach for a flattering jumpsuit or a pair of heels. If I’m headed to the movies, I’ll go with something comfy, such as jeans and a T-shirt, and bring along a jacket, just in case it gets chilly. What I’m actually dressing for is the location; it doesn’t matter whether or not it’s a romantic outing.
Of course, I understand wanting to make a good impression on the first date — perhaps the goal is something that’s sexy yet effortless — but that varies from person to person, and it definitely isn't exclusive to date night (I promise, single people enjoy this, too). Plus, I hate to break it to you, but most of the photos included in these galleries aren’t even being worn on dates. They’re just outfits that might work for one…but many other nights (and days), too.
When it comes to finding something to wear on a date, the tricks are very, very simple. Wear what you’re comfortable wearing, and simply consider where you’re headed when gathering ideas (as in, maybe don’t wear stilettos to mini golf). If you treat this night out — and, therefore, this outfit — the same as you would any other, I promise, you will be fine.
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