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My Favorite Clothes of 2025 (So Far)

My Favorite Clothes of 2025 (So Far)

The 30 best jackets, shirts, pants, shoes, and accessories I’ve acquired this year.

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JAKE WOOLF
Jun 29, 2025
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My Favorite Clothes of 2025 (So Far)
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Original image (center) by Yann Kim

I’m pretty sure New Year’s Day was last week, and yet I woke up today to the reality that we’ve almost hit the halfway point of 2025. But before I start looking ahead to Part Deux of the year (and the fall collections already calling my name), I wanted to take a beat and sit with (mentally, that is) every garment that’s made its way into my closet so far. More specifically, I wanted to reflect on the pieces that have stuck with me—items that went beyond hype or quick-hit gratification and have become bonafide staples I genuinely find myself wearing over and over again.

For starters, this has meant figuring out which items from the classic menswear categories—plain white tees, navy blue suits, jeans, oxford shirts—have differentiated themselves in an ultra-crowded market as elite tier (and worthy of your hard-earned dollars) by virtue of their fits, fabrications, and quality.

But another thing I noticed as I was compiling this list is that I’ve become a lot more invested—monetarily and mentally—in small batch indie brands than ever before. While I’ll follow a great product wherever it comes from (see: the $200 loafers from a globally-famous brand that I officially dubbed my “shoe of the year (so far)”, and the sub $500 suit I haven’t shut up about for the last 2 months.), I’ve found it especially gratifying to purchase a handful products from brands where the founders are front and center, are uncompromising in their commitment to quality, are available to chat via a simple Instagram DM, and every last dollar has a real impact. On that note, special shout out to Ven Space and C.H.C.M., two stores I’ve spent a ton of time in this year, and which continue to inspire me by lifting up burgeoning labels while educating customers (myself included) on their value.

I’ve also fallen deeper down the vintage rabbit hole than ever before, focusing on pieces that have already stood the test of time while giving them a second life in my wardrobe. I’ll never tire of the quiet thrill that comes with finding something with history, and then continuing to write that story in your own way. It’s no surprise then that these pieces remain some of the most cherished in my arsenal.

So with all that in mind, I’ve pulled together my 30 favorite pieces I’ve picked up in 2025. Along the way, I handed out some superlatives—best sneakers, best shoes, best pants, shirts, jeans, even scents, and broke down why each made the cut. So yeah, basically that’s really hit this year, all in one place. As always, links to purchase included below. Enjoy!!!

OTHER POSTS YOU MIGHT LIKE:

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My Favorite Under $100 Summer Shoes

The Best Summer Pants Aren’t What You Think

My New Favorite Summer Suit Is Less Than $500

This newsletter is ENTIRELY funded by subscriptions. I don’t use affiliate links, and all of these products are things I’ve endorsed because I actually like them—though in some cases I did not pay for them. Point is, your subscriptions are both extremely cool and very much appreciated. Thank you!

My 30 Favorite Clothing Items Of The Year (So Far)

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