What clothes have you worn over and over? I’m always reaching for my trusty wool sweater and walking sneakers, and for the past 14 years, I’ve also worn Cuyana’s leather bags on hundreds (thousands?) of everyday adventures…

Classic Easy Tote in Cappuccino

The other day, I brought Cuyana’s buttery leather tote to grab coffee and pastries at our neighborhood café. But I’ve loved the California-based, women-run brand ever since Anton was a baby. I remember feeling drawn to their motto — “fewer, better things” — and how they focus on making classic pieces that you can wear throughout your life.

As a creature of habit, I like having long-term relationships with things I love, and to that end, there’s nothing better than being a coffee shop regular…

…when they make your drink before you even order!

Next I headed outside to work while I sipped my coffee. Roomy and durable, my Cuyana bag was a game changer when my boys were little; and now this one is my favorite work, travel and everyday bag. The tote comes in 11 pretty shades (I like cappuccino and dark olive), and it can be monogrammed, if you’d like to make it feel extra beautiful and timeless.

Nano Zipper Pouch in Black

Thoughts? Which Cuyana bag would fit your life best? (How cute are this pouch and this bow?) See all their styles here, if you’d like. xoxo.

(Photos by Julia Robbs for Cup of Jo. This post is sponsored by Cuyana. Thank you for supporting the brands that support Cup of Jo.)