There’s a really good reason why Ivy style seemingly comes back every fall. The clothes were practically made for this time of year. A sturdy Oxford cloth button-down, some substantial chinos, loafers with a chunky lug sole and those classic campus-ready jackets that always look better with a little wear. But you don’t want to look like you’re headed to an alumni mixer. The way to wear it now is to loosen everything up, play with the proportions and let those familiar preppy staples feel a little less precious.

Start with a relaxed Oxford (slightly relaxed and rumpled is preferable) and throw J.Crew’s archival barn jacket over it. Down below, pleated chinos with a little break over your loafers give the outfit some weight. Then grab an oversized canvas tote, the kind that looks like it could hold a laptop, a couple books and whatever you picked up on the way home. It’s classic Ivy through a contemporary lens. Familiar, practical and particularly good once the leaves start turning.