Have used both High Society (suits/jackets/trousers - ~10 commissions) and MyTailor (shirts - dozens?) for the past ~10 years. Have no experience with MyTailor bespoke, but swear by their MTM shirts (as would many others on here, I suspect). Am a mid-30s native Angeleno in a white collar profession.
High Society occupies an interesting niche. It’s a bespoke product, but without all the bells and whistles. You’re paying for fit and customization—not hand stitching (though it is available for certain items upon request). And it has a price point to match—suits start at just under $2,000. If you want a great fit but can live with machine stitching, it’s a God-send (especially if you have an unorthodox build, as I do). They did my tux, and I’ve brought friends to them for their own wedding tuxes. All their work has been great. I could lecture on the pros and cons (mostly pros) for pages, but I hate typing on mobile devices—feel free to DM me if you would like my 10-year/10-commission perspective.
A quick word on non-local tailors (whether they travel to you, or you travel to them): make sure you have the time (and/or travel budget) to make every fitting you need. As you are no doubt aware, the fittings are where the magic of bespoke happens. I learned this the hard way ~9 years ago with a traveling HK bespoke tailor generally considered far superior to High Society. Even with a full basted fitting, the result was disappointing. There was no substitute for “just one more fitting,” as I enjoyed at High Society—that’s the advantage of having a local tailor. You can go back every week until your commission is “right.” If you want to use an SFO tailor, get ready to fly to SFO at least 3-4 times if you want to do it right. (And with MyTailor, you can drive to their Costa Mesa location.)
As I said, please feel free to DM me if you would like to discuss further. Cheers.
Thank you for the response. I will DM you with a couple of questions. Definitely leaning away from traveling tailors and towards MyTailor, and looking into High Society.
Hope you're staying and safe.