Thinking about outfits this time of year feels different. Colder temps, more occasions, and a desire to simply acknowledge the shift in season calls for color, texture, and choices that feel celebratory but not overdone.

There’s nothing I dislike more than buying something I’ll only wear once. My approach to holiday dressing is practical: reworking pieces I already love, layering in a few thoughtful additions, and playing with timeless themes.

At the start of every season, I pull everything onto a rolling rack and spend an afternoon experimenting with outfits. It’s a ritual that helps me see what I already have, where the gaps are, and what combinations feel good for the rendezvous ahead.

I’m a big believer that creativity thrives with restraints — you can always work with what you already own to create something that feels good. This season, here are five ideas I’m experimenting with.

1. Fair Isle Sweater

I splurged on this Fair Isle sweater last month and I’m absolutely obsessed. If you’re thinking about trying it, size up — I rarely order mediums, and I’m so glad I did. The slightly oversized fit gives it a cooler, more effortless vibe. It works with everything: denim of any wash, leopard, tan cords, and even a pink silk skirt I never expected to pair with it. For accessories, I love it with chunky vintage rhinestone earrings, and if you need cozy basics, the Gap cashsoft socks are an easy yes to wear with boots. I’ve also been getting so much unexpected wear out of this cream belt, even in winter!