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How to Break in Your Baseball Cap Like the Pros

If you've ever wondered why the pros look so much better in their caps than the rest of us, the secret’s out—it’s all in the break-in process. By shaping and softening a cap, especially a 59Fifty fitted, you can give it a worn-in, personalized look that flatters. Luckily, it’s a simple DIY job at home with a few tools: a clothes steamer, a pair of winter gloves (or oven mitts to prevent burns), and your cap.
@mikemonnette Being a jacked and rich pro-athlete is also helpful but we'll work with what we have. If you don’t have a steamer you can also use a tea kettle with the spout left open, or even a hair dryer to apply heat. If you don't have winter gloves you can also use oven mitts, but you definitely need to be careful so as not to burn your hands on the steam or heat. I didn't realize until relatively recently that the hats players were wearing on the field were the same hats I thought of as "flat bills". Once I realized this was the type of hat players were wearing, I started researching how they got them to look so much more round and curved instead of boxy and vertical. I learned the steps I go over in this video and a lot more by watching the channel "Dre in the 616" on youtube (@dreinthe616) – he’s got a bunch more videos on hat education so I’d definitely recommend checking his channel out if you want to learn more. Hopefully this video will be a helpful guide in how to break in your baseball hat, or how to break in your fitted cap, or how to break in your 59fifty fitted cap. #menswear #mensfashion #mensclothing #mensstyleguide #style #styleguide #fashiontiktok #fashion #mensstyle #styleguide #fitted #hat #hats #howto #fashionhowto #stylediy #fashiondiy #fashiontiktok ♬ original sound - Mike

Here's a step-by-step guide to make that flat bill fit you perfectly.

Step 1: Curve the Visor
Most of us are used to seeing 59Fifty caps as flat-brimmed, but to break it in, we need to curve it. Heat the visor over steam for about 30 seconds until it’s pliable. Once softened, use your hands to gently bend the visor into a curve. Don’t worry about going too aggressive—brims tend to straighten out a bit as they dry. Hold the curve until it cools and dries, which should take about a minute.

Step 2: Remove the Creases on Each Side
Next, we want to eliminate any boxy creases on the sides. Steam each side for about 30 seconds to soften the material, then pull the fabric tight, smoothing out the wrinkles. Hold the tension until the hat cools, and your cap should start to look a little smoother and less rigid.

Step 3: Round the Shape of the Crown
To get that professional, rounded look, focus on the crown. Use steam to heat up the top, then press the corners down with your hands for a more subtle, curved shape. Some people even use a round object like a small bowl or ball to help create that perfect dome shape. Repeat as needed until you get the shape you’re after.

Repeat these steps until your cap has the look you want.

Alternatives if You Don’t Have a Steamer
If you don’t have a clothes steamer, you can use a tea kettle with the spout open, or even a hair dryer. Just remember to wear protective gloves to prevent burns!

From Flat to Fitted: My Journey
I didn’t realize until recently that the hats players wear on the field are the same "flat bill" caps many of us know. Seeing how they shape their caps so well inspired me to do a deep dive on breaking in caps. After researching, I found the tips I’ve shared here and much more on a great YouTube channel called Dre in the 616. He’s got loads of hat-care videos, so if you’re interested in cap customization, definitely check him out.

Breaking in your cap can make a world of difference in style and comfort, so give it a try! Whether you’re aiming to break in a baseball hat, fitted cap, or 59Fifty, you’ll have a fresh look that fits like a glove.
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