The Obtainer - 3/31/25, Monday
Cory Ohlendorf
March 31, 2025
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Pull on a Ball Cap
Let’s get one thing straight: style is about confidence. And nothing exudes confidence quite like bending the so-called rules of fashion and making them work in your favor. One of the best moves in the modern menswear playbook? Pairing a casual ball cap with your tailored clothing.
Yes, you read that right. That unstructured navy blazer you're pairing with jeans? Rock it with a vintage dad cap or a jacquard Dodgers hat. Your go-to charcoal suit? Try it with a understated seersucker or corduroy cap for some unexpected texture. This is not about throwing on the battered cap you wear on Sunday morning coffee runs—it's about strategically incorporating a piece of casual headwear into a refined, intentional outfit. Done right, it's an effortless blend of sophistication and streetwise cool.
Why? Because the all-American baseball cap has an innate and undefeated ability to transform any kind of fit. Want to make a casual pairing of a light jacket and jeans look a little more stylish? Try an embroidered cap in a contrasting colorway. Wanna make that suit more casual and less stuffy? Baseball cap. Wanna tell the world that your thrift plug is better than everyone else's? You guessed it: throw an unusual cap on top of that noggin and wait for the questions on where you picked it up. It's up to you if you want to share the wealth or gatekeep your sources. To help you out, here are some of our current favorite picks for the “best caps of Spring 2025” in a range of styles and price points.
Our Picks |
This twill cap pays tribute to the juggernaut of the Negro Leagues, the Homestead Grays.
$58 by Ebbets Field
This classic paneled hat is crafted from a vintage-inspired butterfly pattern jacquard fabric.
$39 by American Needle
Partner
Kick Off Your Worries
at the Door
Indoor wool slide, $79
You’ve just come home from a long day. You’ve been on your feet for hours on end. Leave your stress and fatigue at the door and slip into something more comfortable—namely Kyrgies. Crafted by skilled artisans in the valleys of Kyrgyzstan, the cozy line of footwear are made from felted wool for an incredibly comfortable and durable fit. Their classic style has been refined over generations, which means they’ve perfected important details, such as they’re actually supportive and moisture-wicking. What’s more, you can feel incredibly good about your purchase since the brand isn’t just focused on feeling good, but doing good, too. The slippers are designed using natural materials, including low-impact dyes and leather tanning practices that avoid the use of chromium, a highly toxic metal that can leach into waterways and poison ecosystems. The brand is committed to creating positive social impact by working with a women-owned and operated factory in Bishkek that hires predominantly women and pays everyone a living wage. Plus, as members of 1% for the Planet, they give back to environmental causes. |
 |  Tengries house shoe, $89  Molded mule, $109 |
 Handmade tote, |  |
Explore Kyrgies picks »
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Looking for a new daily carry? Fursac has made the ultimate spring and summer tote ($305) that's the perfect mix between ruggedly casual and elegantly refined. Crafted from tough cowhide suede that's 100% Leather Working Group-certified (meeting all standards for sustainable and responsible leather production), the bag is roomy without feeling too big. It features comfortable rolled top handles and an internal patch pocket for added organization. See all 5 products » |
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