Hello @aaronrulz the Pioneer era is actually not very popular with creators and there are slim pickings.
Women's:
http://historychallengecc.tumblr.com/search/pioneer
This may be more western "town" wear: http://sssvitlans.tumblr.com/tagged/s4historical/page/29 needs mesh here:
http://mystufforigin.com/civil-war-fashion/
Child:
http://cepzid.tumblr.com/post/160699036762/farm-fresh-folk-set-2-child-outfits-conversion
https://www.4shared.com/zip/62LzCmfmba/CF_SundayBestDress.html?
Toddler:
https://segersims.tumblr.com/post/157070653785/country-dress-annie-hat-for-child-toddlers
https://qvoix.tumblr.com/post/156263135878/hi-sweets-so-i-couldnt-decide-on-which-sleeve
Women's ankle boots:
http://kedluu.tumblr.com/post/147252057353/download-thanks-to-sunflower-sim-for-the
Sorry, I couldn't find anything for men. Maybe you could use this?
https://www.thesimsresource.com/downloads/details/category/sims4-clothing-male-teenadultelder-everyday/title/suspender-shirt/id/1314617/
with this one of these hats?
http://femmeonamissionsims.tumblr.com/post/144220456429/floppy-wool-hat-this-is-an-edit-of-the-base-game
http://happylifesims.tumblr.com/post/165828620718/lonelyboy-ts4-wide-brim-hat-finally-ive