Addressed: Lessons from Vogue’s Best Dressed of 2025


Addressed is a weekly column about the act of getting dressed. Anything and everything is fair game for discussion—from animal prints and runway styling hacks, to how to build the perfect winter shoe wardrobe.

Vogue published a comprehensive package breaking down 2025’s best-dressed people yesterday. It was an exciting project here at the office, going to bat for the people we absolutely believed needed to be in the mix. Looking through the final list of 54 people from TK to TK, there are many lessons to be learned, most with universal applications.

If You Love Something, Buy It in Two Colors

Image may contain Jeremy Strong Glenn Tipton Grzegorz Napieralski Daniel Romano Luis Pizarro and Davor Dominiković

Jeremy Strong wearing custom Haans Nicholas Mott at Cannes…

Photo: Michael Buckner/Getty Images

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… and at the SAG Awards in 2025.

Photo: Emma McIntyre / WireImage

This is actually a really important lesson. If you’ve found your dream wardrobe piece, why not go ahead and get more than one? It doesn’t need to be as opulent as getting a custom suit made in two different colors—though that’s really the dream, isn’t it? It can be as simple as getting two of that basic t-shirt you love, or noting the style number and measurements of your favorite vintage jeans and hunting for another pair. The trick is wait for deep discounts to stock up on the things you’ve realized you need more of.

Bonus Jeremy Strong Lesson: Monochromatic dressing is always a yes!

Power Clashing Rules

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Bad Bunny in Valentino separates and Dries Van Noten mary-janes.

Photo: Jamie McCarthy/Getty Images

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Paloma Elsesser in Miu Mi

Photo: The Hapa Blonde / GC Images

Mixing prints is an instant way to elevate your look. Though it may be a scary proposition, consider the fact that as long as you keep the prints in the same color palette, your combo is likely to be a success. (If you want to experiment with different colors, then you may want to keep both prints/patterns in a similar scale.) Another thing that works is to mismatch types of items—think a formal double-breasted blazer with sporty shorts, or a sporty anorak with a more feminine skirt. When in doubt, remember Paula Abdul’s great hit “Opposites Attract.”

Bonus Bad Bunny and Paloma Elsesser Lesson: A little sock and shoe moment will take you a loooong way.

Put a Hat on It

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Pamela Anderson in a leopard print pillbox hat.

Photo: Neil Mockford / GC Images

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Cole Escola in a dramatic bonnet.

Photo: Michael Loccisano/Getty Images

I have written a lot about hats this year, and I have definitely written about this Pamela Anderson look at least three times—but can you blame me when it’s this good? A hat not only adds an unexpected level of pizzazz to your look, it also makes people ask Who Is She? Do yourself a favor this holiday break and take some time off from doomscrolling and search for vintage hats on eBay instead, until you find one you like. There will come a time when you are getting dressed and you’ll realize a little (or an enormous) hat is exactly what you need. And you’ll be happy you heeded my advice.

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