@Humbloom I'd suggest unlocking Blacksmith, Farmer, Flockherd and Clothier first!
Clothier and Blacksmith unlock pretty much all craftable clothes + the ability to gather Spool of Thread in the case of Clothier.
Flockherd and Farmer can gather items needed for Clothier items, Wool & Cotton respectively. Though Cotton cannot be gathered in winter, so if you're short on materials I'd suggest putting unlocking Farmer on low priority and buying all the Cotton you think you may need from Whiskers before winter hits.
If you don't mind paying extra for Clothier/Blacksmith items, or if you have no plans of using them, then go ahead and start dressing those cats up! It's a good money sink and a nice way to spend time on the site before Adventuring hits.