Fall is about layering and the jacket is essential. For year-to-year wear stick with tailored styles like the one-button blazer and casual jean jackets. Tweed, suede and corduroy are favorite jacket materials for tailored or casual. The general trend over the past few years leans toward snugger fits (no baggy looks) and vintage-y touches (suede patches on the elbow, bomber jackets, "worn" looks).
Menswear or haberdashery prints encompass houndstooth, plaids, pinstripes and checks. Fall is the perfect season for masculine prints to appear made up in suits, pants, jackets, coats and dresses. When buying classics, remember that you'll tire of prints faster, so stick with smaller-scales (pinstripe vs. large houndstooth). Pair a feminine top and accessories with menswear for maximum style.
Wearing pants in cooler weather is largely a practical matter (keeps legs warmer!), but they impart tons of style, too. For maximum wear, stick with jeans with a lower waist and slight flare (or bootcut) in a darker wash. Tailored pants in menswear prints are a great investment, just remember to go with traditional silhouettes that defy trends: cuffs, flat-front or soft pleats.
Although there are always exceptions, fall clothes often appear in earthy hues (olive, chocolate, stone) and jewel tones (deep purple, emerald green, ruby red). Black and navy are always dependable, but don't be afraid to add shots of hot colors like red or fuchsia and even pastels to your mix. White is usually reserved for blouses in Fall (looks great with menswear prints).
Boots are enormously popular for fall and winter, so invest in several pair and you'll always have shoes for this season. Shorter boots with a heel look great with pants. Mid-calf boots can be worn with cropped pants or skirts. Knee-high boots go great with all types of skirts. Pair your boots with either bare legs or tights to complement the outfit.
Natural fibers are a top choice for sweaters: wool, cashmere, cotton. They breathe better and are great for layering. Look for classic choices like solid turtlenecks or Vnecks. Lightweight silk or blend can even take autumn style to tropical climates.
Stash the straw, fall means it's time for a more serious bag. Suede and leather are natural choices in everything from earthy browns to warm reds. If you lean toward logos, now's the time for a status bag to add pizazz. Remember to scale the bag size to your size (small bags for small frames, up to larger bags to larger frames).
This humble fabric may get touted by some designers as a year-round fabric, but who are they fooling? Nothing says "Autumn" like plush cords in everyting from jeans to jackets to bags. For maximum flattery, watch the wale (that's what those stripes are called): thin wales add texture without heft, while the wider wales pack on the bulk.