28. The Tweed Blazer — Whether you opt for a simple, nipped-at-the-waist jacket of a boxier version, a tweed blazer is a preppy fall topper that will never (and we guarantee it!) go out of style. No need to wear it with that plaid, loafers or other trad basics — we like ours with acid-hued dresses and statement jewels, and printed, flowing skirts.

H&M Blazer, $19.95, available at H&M; Rachel Comey Quip Jacket, $886, available at Rachel Comey.