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outfits prompts and you [lifestyle]

a guide to intentionality

Oftentimes I find myself struggling with intentionality in my outfits, merely throwing the basic array of my favorites together into an acceptable pattern as I gather enough energy to get to breakfast. It’s a difficult pill for me to swallow. I have never been a capsule wardrobe person; my goal has never been to be able to “get dressed in the dark,” as all the “problem-solver” fashion experts claim to be able to teach. I love clothes too much to limit myself to a minimalist, interworking system. I love the way they feel, their colors, their patterns, their age and construction, and—perhaps more than anything—I like having a lot of them. So how do I still end up wearing the same things in the same ways? 

Well for one, getting up in the morning is hard. I know, sometimes it’s easier to just throw on the shirt that you know fits and goes with everything. Especially when the other option is to break out the pink gingham that’s been staring at you from the dresser drawer for a week. I’ve been wearing tweed suits quite a bit lately, just to save me the trouble of matching. Sadly, I can’t dress like Dean Acheson all the time, but what I can do is devise a system of inspiration to give those morning outfits a little more spice: Outfit prompts!

Outfit prompts are a pretty simple concept: you take a prompt—think of those things you see attached to a very bad short story on Reddit—and attempt to translate the image or scenario into your outfit. This can range from rather simple constructions based around a color or a broad theme (The Man with the Yellow Hat from Curious George) to the extremely specific manifestations of one’s own inner fantasy grafted onto the outside world (The King in Yellow). Perhaps you want to revel in the world of a movie you watched the previous night. Maybe you like a certain aesthetic of an era past but have lacked the stones to pull it off—use a prompt and go for it. My fiancé and I do this all the time, usually taking inspiration from the world around us and turning it into characters. It came in handy in the summer—global warming being so hot it takes a concentrated effort not to go outside wearing a linen sack as an outfit. We imagined worlds of New England summers, Ralph Lauren iconography, and Bostonian living into our styles and fits. Not only does it make getting dressed in the morning a little more fun, but I often find it makes our outfits more in tune with the season. This is extremely vital to me, as I always default to the same color palette of browns and grays when I get dressed for fall, winter, or the middle of July. Outfit prompts can force you out of your comfort zone and allow you to explore the various ins and outs of what makes your fashion yours. To this end, I recommend you adjust your prompts to the specific avenues of style that you would like to explore. Instead of just saying “bread” and seeing what happens when you loaf from bed to clothes you could instead go “the fractals along the cracks and ridges on a fresh loaf of sourdough” and explore how much texture and visual depth can change an outfit. Isn’t that a lot more fun?

Outfit prompts are a great way to add some pizazz back into your morning routine. As for a place to start, try dressing like characters from your favorite movie, or hone in on a time period, or even a personal interest. Because I’m generous, I’ll be leaving you with some special outfit prompts to get you started. Take these as a point of expansion for the mind to run and develop your own settings and characters. Regardless of your methods, have fun throwing on those weird pieces from the back of your closet and let me know what you come up with.


Sean’s Special Sartorial Setting Suggestions:

  • Bookstore Grandpa
  • Neapolitan Nobleman in the 1930s
  • ’80s Preppy Guy with Red Pants et al.
  • Serpico Era
  • Miami Vice
  • All Night Italian Party in the ’80s
  • Parisian Style through the Years
  • Any Character from Sabrina (1995)
  • Lovers on the Run in the 1930s
  • Gay Lovers on the Run in the 1930s
  • Artist Summering on their Rich Friend’s Estate
  • Expat Journalist
  • Ralph Lauren Ad
  • The Glory Days of the French Riviera 
  • Mr. Darcy-core
  • Wes Anderson Movie
  • Dashing Aviator
  • ’70s YSL Vibes
  • The Impressionist Landscapes of the French Countryside
  • Abruzzian Estate
  • Secret Witch Living Amongst the People
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