Tailoring the perfect shirt, pants, and jacket

I’ve had custom clothes made for me twice, once by Pete the tailor, so if you’ve never had custom clothes made then I have infinitely more experience in this area than you 😂.

I recommend bringing clothes and photos of clothes with elements you like so that you can show them to the tailor. You want your tailor to know how you want to look and feel. Materials-wise, it’s good to aim for 100% cotton and wool.

The risk with getting clothes tailored is that you can't try them on ahead of time—this article ahould reduce that risk for you.

Elements to consider when tailoring the perfect shirt

• Sewn in collar stays
• Double layered collar
• Style of collar, angle. British, Mandarin, rounded
• Double layered shoulders to reduce wrinkling and protect against pointy hangars (it’s time to get better hangers!)
• Double layered cloth under middle buttons on both sides to reduce wrinkling and prevent show-through
• Cuff style, rounding radius or cut angle, French
• Length of shirt to accommodate staying tucked, untucked casual wear, or both
• Weave of the cloth: some weaves are much more wrinkle resistant than others. 100% cotton can be quite wrinkle resistant
• Material: cotton, or cotton/linen blend for summer (pure linen gets wrinkled too easily for me)
• For white shirts, a very very light purple helps them stay white longer
• Chest pocket or no pocket. Nice for the pocket to be big enough to hold your passport while going through the airport.
• A couple of spare buttons attached where no one will see them
• It fits you well based on your measurements. If you expect to gain/lose weight in the next 5+ years then ask for that literal breathing room.
• You’ll likely want at least 3 white shirts with normal British collars and cuffs, and the rest can be different colors and styles.
• Price-wise, I paid $42 per shirt a long time ago, which is probably still a good price considering untailored shirts from better brands go for $50+, but of course shop around.

Elements to consider when tailoring the perfect pants

• Must be slightly stretchy. You will hate them otherwise and never wear them. For example, 4% elastane.
• They fit you well based on your measurements. Personally I feel straight leg pants hide your silhouette too much.
• Pockets that don’t drop stuff
• Back pocket that is wide enough for your U-Lock
• Basic color choices: navy, charcoal, black, khaki

I don’t have as many items here because I think pants are easier to get right.

Elements to consider when tailoring the perfect blazer / suit jacket

• If you overheat easily and live in California like me, getting a summer jacket that doesn’t have a back liner helps a lot. It’s also nice how much lighter it is which makes it more comfortable to wear.
• Decide on the length at your wrist and length at your hips that fit your style: be careful you’ve not working with a tailor who prefers mobster cuts 😂.

Thank you Alex Cohen, you got me started on all of this and your advice has been crucial! 🙇🏻‍♂️ A couple of tips from him:

• Three pillars of style: fit, material, color
• Avoid wearing more than 3 colors in an outfit

What do you look for in your clothing? Let me know.

May you look good and feel good,
David Trejo
Email me ✉️

PS If you’re just getting started on dressing more fashionably, you probably don’t feel confident enough that you’d want to go to a tailor. Ask your most fashionable friend to go shopping with you so you can make purchase decisions and don’t get overwhelmed by analysis paralysis. Uniqlo and Luigi Fusaro are a couple of my favorite stores where you can pick up basic outfits for good prices (make sure to check the materials!).