I've been wearing barrel jeans - (and their cousins horseshoe jeans) - since 2019, and wear them with loafers, ballet flats, hi-tops, low-tops, and boots. Some of my barrels are full length, and others cropped. See pics:
Apart from one pair of lug sole boots, my shoes are refined and not chunky. They are flat or low heeled. My boots are tailored on the ankles so they work under the width of the hems of all bottoms, really. It's quite easy!
Actually, I wear my loafers, booties, and sneakers with every bottom in my wardrobe! I don't differentiate much with my footwear because I don't have much variation. I wear very few types of shoes
