Caps with Tailoring
Who doesn't love a good ball cap? Here's an inspiration album full of ball caps worn with tailoring.
![Caps with Tailoring](/content/images/size/w1200/2025/02/play-lee-7-1.jpg)
Honestly, this is easy. This album is sort of a successor to my previous album on sneakers with tailoring, but it's so much easier to pull off, it doesn't really even need a write up. Three simple approaches:
- Build a casual outfit and throw on a jacket
- Think of a sport jacket as something you wear for sport, feel casual in it, throw on the ball cap.
- Dress up, use the ball cap for some formality contrast, do that sort of high-low thing with intentionality.
Really, though, it's not hard. You don't need a guide, you need inspo.
So here it is, pure inspo. Enjoy.
![](https://thesecondbutton.com/content/images/2025/02/jon-alan-victory-motel-white-pants.jpg)
![](https://thesecondbutton.com/content/images/2025/02/jon-alan-deus-cap-sfc-pants.jpg)
![](https://thesecondbutton.com/content/images/2025/02/jon-alan-pepsico-phone-call.jpg)
![](https://thesecondbutton.com/content/images/2025/02/jon-alan-nasa-cap-v-neck.jpg)
![](https://thesecondbutton.com/content/images/2025/02/jon-alan-victormy-motel-at-buck-mason.jpg)
![](https://thesecondbutton.com/content/images/2025/02/kiddkonni-at-pitti.jpg)
![](https://thesecondbutton.com/content/images/2025/02/henrik-2.webp)
![](https://thesecondbutton.com/content/images/2025/02/henrik-1.webp)
![](https://thesecondbutton.com/content/images/2025/02/henrik-3.webp)
![](https://thesecondbutton.com/content/images/2025/02/henrik-4.webp)
![](https://thesecondbutton.com/content/images/2025/02/henrik-5.webp)
![](https://thesecondbutton.com/content/images/2025/02/will-thedonsclub.jpg)
![](https://thesecondbutton.com/content/images/2025/02/play-lee-3.jpg)
![](https://thesecondbutton.com/content/images/2025/02/play-lee-1.jpg)
![](https://thesecondbutton.com/content/images/2025/02/play-lee-7.jpg)
![](https://thesecondbutton.com/content/images/2025/02/play-lee-6.jpg)
![](https://thesecondbutton.com/content/images/2025/02/play-lee-5.jpg)
![](https://thesecondbutton.com/content/images/2025/02/play-lee-8.jpg)
![](https://thesecondbutton.com/content/images/2025/02/play-lee-2.jpg)
![](https://thesecondbutton.com/content/images/2025/02/play-lee-4.jpg)
You people really ought to follow Play Lee.
![](https://thesecondbutton.com/content/images/2025/02/shot-for-fudge_magazine.jpg)
![](https://thesecondbutton.com/content/images/2025/02/ivan-ivy.jpg)
![](https://thesecondbutton.com/content/images/2025/02/stephon-and-ivan-gaming.jpg)
![](https://thesecondbutton.com/content/images/2025/02/ivan-check-jacket.jpg)
![](https://thesecondbutton.com/content/images/2025/02/stylesurlaville.jpg)
![](https://thesecondbutton.com/content/images/2025/02/kunle_x-2.jpg)
![](https://thesecondbutton.com/content/images/2025/02/kunle_x-3.jpg)
![](https://thesecondbutton.com/content/images/2025/02/cody-wellema-in-ballcap---taillour-suit.jpg)
![](https://thesecondbutton.com/content/images/2025/02/photo-fw20.jpg)
![](https://thesecondbutton.com/content/images/2025/02/mordechai-ss22.jpg)
![](https://thesecondbutton.com/content/images/2025/02/suit-and-scarf-fw20.jpg)
![](https://thesecondbutton.com/content/images/2025/02/ralph-nakash-ss21.jpg)
![](https://thesecondbutton.com/content/images/2025/02/air-ties-fw20.jpg)
Aimé Leon Dore
![](https://thesecondbutton.com/content/images/2025/02/quentin.menstyle.jpg)
![](https://thesecondbutton.com/content/images/2025/02/jason-jules-for-drakes-navy-db-light-blue-hat.png)
![](https://thesecondbutton.com/content/images/2025/02/drakes-seatown-1.jpg)
![](https://thesecondbutton.com/content/images/2025/02/Transitional_AW24_LayoutDOC33.webp)
Drake's. Note that Drake's hats are really short. Good if you have a short head, I guess.
![](https://thesecondbutton.com/content/images/2025/02/DSC04852.jpg)
![](https://thesecondbutton.com/content/images/2025/02/harris-tweed-RJ---omtc-blue-2.jpg)
![](https://thesecondbutton.com/content/images/2025/02/suit-runaway-linen.jpeg)
![](https://thesecondbutton.com/content/images/2025/02/fit-from-drew-joiner-audioPXL_20240504_220217870.PORTRAIT.ORIGINAL-01.jpeg)
![](https://thesecondbutton.com/content/images/2025/02/buck-tee-brown-db-3.jpg)
![](https://thesecondbutton.com/content/images/2025/02/Drakes-without-Drake-s-1PXL_20240226_170953450.PORTRAIT-01.jpeg)
![](https://thesecondbutton.com/content/images/2025/02/navy-blazer-and-jeans-1.jpg)
![](https://thesecondbutton.com/content/images/2025/02/2021-fit.jpg)
![](https://thesecondbutton.com/content/images/2025/02/rafael-brit.jpeg)
I've done this myself, once or twice. Hats from Ralph Lauren; Todd Snyder x New Era; my Alma Mater; and Alfargo's Marketplace. It's better to get your school, your favorite sports team, or a club you're part of than get something boring and pointless.
Further Reading
- Sneakers with Tailoring
- On Baseball Caps—and Logos in General | Permanent Style
- Lookbooks from ALD and Drake's
Special thanks to Ivan for helping me round out the album.