I think I've also got some country boots that needs a touch up. Any advice
if this is even worth modernizing.
By country boots I assume you mean cowboy boots? What color are they and what style? I'm picturing something like this:
Cowboy boots are such a great winter-to-spring transition piece. AND, in my personal opinion, they are worn BEST when they are OFF-trend, not on-trend. ie., when no one else is wearing them :) The best kinds are the classic ones that look authentic with real leather and bonus if they have scuff marks. My favorite colors are a rich dark coffee-brown as shown on the right of the link I have there, or RED. I have a pair of red cowboy boots and they always come off as unique when I pull them on.
Cowboy boots over leggings and a long fitted shirt (make sure the hem hits at least mid-thigh) would be a great casual on-the-go look. Paired with a slouchy hobo and, if you have an hourglass figure, a cinched belt that matches the boot color, this look would be great for spring. If you have great legs like the women in the link, you don't need leggings. And the flowy dress makes the outfit cute, but watch out for getting too little dramatic if you get too flowy.
If you want a more subtle "cowboy boot" look, bootcut jeans are your answer! Jeans with just a little flare in them give your body shape. You don't have to show the whole boot to get that "Western" look. Just let the jeans fall over the boot. Try them with a medium-width brown belt and a plaid or checkered shirt that isn't long, not the tunic styles, but slightly shorter to show off glimpses of the belt.
Another suggestion: Boots, bootcut jeans over it, loose fitting vintage-soft worn-in "I don't care" tshirt, maybe black-ish or yellow for a playful statement, or a basic super-soft tee, and an unbuttoned loose fitting button-up over it. Says completely casual with a twist! Accessorize with a funky necklace and oversized sunglasses and you're good to go.
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