Give any outfit Annie Hall cred with this charcoal polyester-blend fedora.To buy: $58, michaelstars.com (available mid-September).
Your dad’s old necktie gets remade into a totally modern polyester dress.To buy: $89.50, landsendcanvas.com.
Show off your shape by cinching your waist with this slim cognac leather belt.To buy: $34, lodis.com.
Chunky links always add a little polish.To buy: $65, 212-685-1248.
Go gray whenever black feels too severe.To buy: $14.50, nordstrom.com.
Loafers + platforms = preppy glam.To buy: $50, hm.com for stores.
Use a silk scarf the same way a man does a pocket square—to punch up an understated look.To buy: $38, michaelstars.com (pattern available mid-September).
Cable knits can be boxy, but this cotton blend has a snug, Joan-from–Mad Men fit.To buy: $59.50, bananarepublic.com (available end of September).
Quirky piping takes the stuffiness out of tweed.To buy: $69.50, 888-563-8444.
An oversize leather-strapped watch commands attention.To buy: $50, timex.com.
The I-can’t-believe-it’s-polyester factor alone qualifies this as a steal.To buy: $35, hm.com for stores.
There’s no doubt who wears these pants: The female-friendly polyester-blend cut and the cinched sash waist give it away.To buy: $80, shopbop.com.
Irregular (in a good way), these resemble freehand circles.To buy: $40 for 12, 212-685-1248.
Keep your loved ones (or at least their photos) close with this five-locket charm bracelet.To buy: $75, 212-685-1248.
A true designer find, complete with zigzag suede and faux-bois heels.To buy: $40, target.com (available mid-September).
A knee-length trench is classic in khaki—and expected. In brick red, it becomes dashing.To buy: $50, target.com (available mid-September).
Tired of hemlines creeping up your thighs? At 42 inches in length, this black microdot viscose-blend sheath is designed for tall women.To buy: $95.50, longtallsally.com (enter the code RS1234 to get this discounted price through September 30).