OLD FASHIONED

OLD FASHIONED

THE WARDROBE: HALLOWEEN EVERYDAY

The other 'holiday dressing'.

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Ruby Redstone
Oct 16, 2025
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Often my topics for THE WARDROBE franchise within this newsletter are chosen from questions I get asked all the time in real life. (How would you you style overalls? What’s the best way to dress up shorts?) I can safely say, however, that no one has ever come to me with the burning question of how to incorporate more Halloween items into their outfits. And yet—and yet!—here I am once again urging you to do so.

There is so much talk in fashion media about ‘holiday dressing’ in November and December, all while we woefully neglect that a holiday meant for the sole purpose of dressing up falls on October 31st! There is no reason that we shouldn’t celebrate and anticipate Halloween’s arrival with equal zest. In fact, there’s no reason why a few Halloween treats shouldn’t be part of your wardrobe all year long, and I think I’ve made a compelling case for that below. I’ve ranked the Halloween-themed outfits from easiest to most difficult to execute, should you be scared of adding a little spookiness to your life. The hardest of these looks could easily qualify as low-lift costumes in and of themselves, which I also think is an underrepresented category in fashion media. Wear them to a bar, to your kids’ school Halloween dance (I certainly plan to), or just to pass out candy from your doorstep. It’s the most wonderful time of the year.

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