What do you wear when the weather gets cooler? After a fun summer of trends, I’m looking forward to kicking off the fall with classic staples. The first time I pull on straight-leg jeans or a tissue turtleneck, it feels like returning home after vacation.

On chilly days, I’m excited to wear an iconic rollneck to the park with the boys or to my next soup group. And if you want an everyday sweater recommendation, I’ve worn this workhorse on repeat for years — it’s effortlessly sexy on its own or layered over a chambray shirt.

For outdoor dinners or work meetings, this cocoon sweater-blazer is pretty and super cozy.

I’m also into playing around with denim — I love nothing more than denim on denim and covet this whole vibe: denim jacket, blue shirt, jeans and loafers. Plus, gold hoops and a red lip! #doneanddone

When it comes to chinos, the slouchier, the better. And wouldn’t these sneakers be perfect for long podcast walks?

What are your thoughts on this skirt? I love this for anyone who’s feeling flirty! I also adore slip skirts — my bff Gemma wears them on repeat and looks so cute every time.

Thoughts? What fall styles are you into? Here’s J.Crew’s lookbook, if you’d like some inspiration. (This dress and these boots are both great.)

Great news: Get up to 40% off wear-now styles & extra 30% off sale styles, use the code SHOPSALE. See the full sale here. Thank you!

(This post is sponsored by J.Crew, a brand we’ve loved and worn since high school. Thank you for supporting the brands that support Cup of Jo.)