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I’m kinda old school here. Most of my designs are type-based. So I’m thinking legibility from the start. Icons are cool, but the reality is that you need to spend pretty heavily before you get to where you can use an image without the name.
And, like all visual design, investigating the market, positioning, and usage come first. For example, if it’s going to be seen exclusively online, then it’s important to remember that we passed the time when more people see the internet on PHONES rather than computers long ago.
Good question, I suppose I have my favorites I tend to lend towards. However, I also have the benefit of being with a team and we all put input into these type of decisions so I rarely make the final font decisions all on my own.
Start by getting alignment on the brand's qualities, tone, voice...
Modern vs classic
Edgy vs safe
Artsy vs business-like
Global vs homegrown
Bold vs approachable
...that kinda thing. In many font tools and sites, you can type those qualities in and it will return results that have been tagged accordingly. ChatGPT can probably give you a list quickly as well, but it will probably lean toward the most well known.
Before messing with a tool, it can be helpful to consider the font characteristics that will match the feel you're aiming for: serif vs sans serif, tried and true or new and niche, etc.
Then you gotta just look at a bunch and do some experiments. Additional considerations are how much does it cost, who needs rights (the whole org or just creatives?), does it have all the characters and weights you need, does it play nice on web and apps or do you need easy to access substitutes.