thesilentist

Buttons have to deal with the level of formality.

Single buttons have their roots in the single-breasted dinner jacket or tuxedo. If you want your jacket to have an increased level of formality, you'd go with a single button.

Two-button suits are more standard, common for business and every-day suiting. Formal enough for the majority of situations when you'd wear a suit, but not quite "after six" level of formality for an evening event or dinner.

Three-button jackets should be left to casual suits or odd-jackets. Adding more buttons on the single-breasted suit adds an increased level of informality. Works best on casual, seasonal fabrics like seersucker, linen, tweed, corduroy, etc.

Double-breasted jackets have their roots in the military and are often paired with peak lapels, which are more formal than the notched lapels of most suits. So, a double-breasted suit would be definitely on the more formal end.

So, I wouldn't say that buttons are about "personality" as much as it is the situation in which you'll be wearing the suit.

I've had experience with both Spoon Tailor and Indochino. TL;DR: go with Spoon over Indochino if it's in your price range.

I've used Spoon for about 9 shirts and talked with them extensively about their MTM suiting. The quality is much higher on their suiting and the fabrics are nicer. Plus, as far as MTM goes their process is closer to bespoke. Multiple fittings are involved and they have a local tailor that does the pattern, if I recall.

Indochino's an affordable option out there, but they're definitely going the cheaper MTM route. Their suits are based off of ready-made patterns. They can't really do stuff like account for sloped shoulders or weird drops. Their details are also a lot more "fashion forward" (like skinny lapels) that will look dated in a few years. I went to their traveling tailor event in Chicago a few weeks ago and got a suit made up for me as a review unit for a blog I write and I can't say I'd highly recommend them over other MTM services that might charge more or ready-to-wear options that cost the same.

If you're looking for something at Indochino prices yet in "ready to wear", then I'd suggest checking out Suit Supply. Decent cuts, good fabric, good construction, affordable intro-level prices.