There are certain styles that may be having a moment, but never really go out of style—and the equestrian aesthetic is one of them. Tailored wool blazers, beautiful herringbone and heritage plaids, rich chocolate browns, riding boots, crisp button-downs, great denim, and timeless leather accessories have been part of well-dressed wardrobes for generations. Right now, we’re seeing this look everywhere, but for me, it feels much more personal than a trend.

Growing up in West Virginia and later going to school in Kentucky absolutely shaped my personal style, and this classic equestrian aesthetic has always been a part of it. There’s something about the combination of American countryside style and British heritage dressing that I will forever love. It feels polished without being precious, practical without sacrificing style, and incredibly chic at any age.

For this edition, I pulled together my take on the Equestrian Grandmother aesthetic with pieces that feel classic first and current second. Think a beautifully cut wool herringbone blazer layered over a crisp shirt, wide-leg denim with a great leather belt, tall boots, barn jackets, suede, cashmere, and those rich, earthy colors that somehow make everything in your closet look more expensive.

And if there is one piece I will always advocate investing in, it’s the classic wool herringbone blazer. Buy a beautiful one and take care of it, and you can wear it for decades. These are the pieces worth spending a little more on because they only get better with time—and they can be styled a hundred different ways, from jeans and boots for everyday to trousers and loafers for something more polished.

A wardrobe rooted in quality, heritage, beautiful fabrics, and classic silhouettes doesn’t belong to a particular season—or a particular age. So consider these looks my take on the trend: a little equestrian, a little English countryside, a little Kentucky, and very much the kind of timeless style I’ll always come back to.