My biggest fear is looking like I'm going to a bachelorette party in Nashville when I wear cowboy boots.😂 Long gone are those days! I think that the key to pulling off cowboy boots in your 40s is to oversize everything else. I love these Anthropologie shorts, they're sort of an elevated boxer, but you could totally wear a pair of cute oversized boxers. They are sold out but I linked a pair of boxers that I would wear instead. This sweater is from…wait for it… Walmart! It’s so soft and such good quality for under $20. I've had these boots for over a year, and they've held up so well. They are also shockingly comfortable to wear in the salon all day. Yay, fall transition season! Dress because it makes you feel happy. ❤️ Sweater-M Shorts-M Boots-TTS/8 LTKShoeCrush LTKOver40 LTKFindsUnder50