In 1977 Diane Keaton walked through Annie Hall in khakis, an oversized white shirt, a black vest, a blue tie and a floppy hat, and fall dressing got a new rule. TCM credits costume designer Ruth Morley, Keaton herself and Ralph Lauren with that look. Morley said anyone could copy it, because the pieces were already in stores. I love that. Nothing was rare, it was just put together with nerve. I went deeper on a related idea in Diane Keaton style: The Annie Hall Wardrobe, Made Personal.

 

That is how I think about fall outfits now. You do not need a new wardrobe, you need a few solid layers that already belong to each other. This edit is built that way: a jacket, a knit, a trouser, a boot and a skirt, all in the browns, creams and plaids of October.

 

The jacket comes first, and suede is my pick. The word itself is French for "gloves of Sweden", used in English by 1859, so this is a glove leather grown up into outerwear. The Shyla in mocha is a clean faux suede with a collar and a zip front, and I would wear it over a white tee and straight jeans. The Cooper in chestnut has a cinched waist and a funnel neck, which makes it the sharper pick for a dress. The Trevanna bomber in chocolate is real lambskin suede with ribbed trim, and the camel Lauren Ralph Lauren flight jacket is the same idea in a lighter shade. For a more grown-up day I would reach for the Quince blazer in java brown, and the black Cole Haan leather bomber is the one for nights out.

 

Practical tip: carry one dry suede brush. Suede cannot go in a washing machine, and water alone can stain it, so let any damp jacket dry naturally away from heat.

Aran knitting is younger than it looks. Most historians date it to the 1890s and early 1900s, and the sweater took off abroad when the Clancy Brothers wore theirs on The Ed Sullivan Show in March 1961. The cable pattern on a fisherman sweater is a century old, which is why it still looks right now.

 

The Pendleton fisherman sweater in tan donegal has cable and diamond stitches, colorful flecks in the yarn and raglan sleeves for a roomy fit. The Barbour Ambleside in navy is a wool and cotton turtleneck with a chunky roll collar, and I would put it under a camel coat. The Abercrombie navy fair isle roll neck brings a cream and blue yoke if you want pattern. For a cardigan, the Rowing Blazers one in beige donegal wool has a small embroidered sheep, which makes it the funniest piece here. The Ralph Lauren wool and cashmere cardigan in cream is the quiet one, and the long oatmeal Splendid has a shawl collar and pockets for cold mornings. If you want to keep going, Polo Ralph Lauren Knitwear: Cardigans, Cable Knits and the Bear is the one I would read next.

 

The House of Sunny Peggy in brown has a detachable faux fur collar and cuffs and a tie neckline, so it works with the fur and without. The Good American sweater in berry noir is a ribbed wool and cashmere blend, and I would wear it with the FRAME wine corduroy.

 

Fitting test: lift your arms and check that the cuffs stay near your wrist and the hem does not ride up. Look for raglan sleeves or a snug rib.

 

What I would skip: a chunky knit and a thick scarf in the same weight. Pick one big texture per outfit.

Wide legs need a long hem, and the hem is where I would start. Stand in them in the shoes you plan to wear. The fabric should skim the top of the shoe without dragging on the floor, so a flat loafer and a heel need two different lengths.

 

Corduroy is the easiest fall fabric to love. The FRAME Le Slim Palazzo in wine is a wide-leg corduroy with a button closure and zip fly, and the AGOLDE Ren in bone is 100% cotton cord with a high rise. Both look good with a brown suede layer. For something dressier, the Citizens of Humanity Ines in gris is 100% wool with pleats and a tailored waist. The Theory charcoal plaid, the Reiss Derby in charcoal pinstripe with a drawstring waist and the brown glen plaid brushed wool from Lauren Ralph Lauren all lean office. I would wear any of them with a cream knit tucked in.

 

Then the jeans. The DL1961 Karmine in dark sea is a stretch denim with a high rise, and the Abercrombie high rise wide leg in dark wash has a drapey rigid denim and a long leg, which is the better choice for boots. Dark denim reads dressier than mid-wash, so a tweed or suede layer sits well on top.

 

Buying test: sit down in them. A high rise should not dig in and the zip fly should stay flat. With wool trousers, check the lining and the pleats for pulling when you sit.

 

What I would skip: pale jeans with heavy wool in the same outfit, because the two weights fight each other.

André Courrèges introduced what became go-go boots in 1964, and Nancy Sinatra's 1965 hit "These Boots Are Made for Walkin'" made them famous. The rule from that decade holds: the taller the boot, the shorter the hem, so a knee boot sits well with a midi or a mini skirt.

 

The Free People Kiki in chocolate suede has a kitten heel and a pointed toe, and it is the soft option. The Reformation Dominique in syrup leather has a stacked heel, while the Tory Burch in brown suede has a block heel and cap toe. The STAUD Wally in truffle has a sleek tall shaft that slides under wide-leg trousers. The Steve Madden Joette in black leather has a towering block heel, so I would keep it for evenings.

 

Loafers are the flat answer. G.H. Bass was founded in Wilton, Maine in 1876, and in 1936 it launched Weejuns, which it calls the world's first penny loafer. They were a spin on a Norwegian farm shoe, and kids soon slid coins into the slot, which gave the shoe its nickname. The wine box leather Whitney is that shoe with a cushioned footbed. The Dolce Vita Baxen in russet has a round toe, and the Sam Edelman Loraine in black has polished bit hardware.

 

Fitting test: for any knee boot, check the shaft at your calf and bend your knee to see if the top edge digs in. A loafer should hold your heel without slipping.

 

What I would skip: a boot with a pointed toe and a tight wool sock. Go with a thin sock.

A midi skirt is the easiest way to turn a fall sweater into an outfit. The length lands mid-calf, so it pairs with knee boots and flat loafers.

 

For suede, the brown coffee A-line midi has tonal topstitching and a velvet-soft finish with a smooth lining. The English Factory faux suede midi in brown is a super-stretch fabric with a hidden side zip. Suede skirts take the same care as a jacket, so brush them and keep them dry.

 

For wool, the Ramy Brook Abby in heritage brown is 100% wool with a split hem, a tie self-belt and on-seam pockets. For texture, the LE BOP Arlen in hunter green is 100% cotton corduroy, made in the USA, with a covered drawstring waist. Pair it with the cream cardigan.

 

Then the plaids. The Joe's Jeans Ines in camel plaid is lined lyocell, the Barbour Hazelwood wraps with a buckle on the side, and the Ralph Lauren tweed in burgundy has a fitted yoke and a flared hem. The Sanctuary slip skirt in green and black plaid has a bias drape, and I would wear it with a heavy knit and boots so it stays casual.

 

Buying test: walk in it. A wrap or a slip should stay closed and the lining should not cling to tights. Check whether the plaid lines up at the seams.

 

What I would skip: a plaid skirt with a plaid jacket in different scales. Keep one pattern per look.

I would begin with the jacket, since it sets the colors. Pick suede in a brown you like, then add one cable knit in cream or oatmeal.

 

Next comes the bottom half: wine corduroy or a dark wide-leg jean for days, and a plaid or suede midi when you want a skirt. Finish with loafers for errands and knee boots for nights, and keep the brush handy.

 

Ruth Morley was right that anyone could copy the Annie Hall look, because it was only clothes you already knew. I think good fall outfits still work like that: nothing new, just better layers.