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The Outerwear: A Thigh-length Blazer

Lower Layer: So long as it's thin, most any top works: T-shirts, tank tops, sweaters and button-downs. Something too thick, though, like a chunky knit or scuba sweatshirt, will bulge beneath the jacket's trim cut.

Top Layer Option: To transition this piece from Indian summer to late fall, try a slightly shorter hip-grazing vest. For a more casual feel, pick something puffy and sports-inspired; sleeker quilted styles are better for commuting to work.

Styling Tip: Because most blazers have narrow sleeves, don't try to roll them with something wrist-length beneath—it looks sloppy. Instead, peel the cuffs back a few inches to let the contrasting fabric peek through.

The Outerwear: A Boxy Tweed Jacket

Lower Layer: Longer cut T-shirts and tanks, hanging loose or tucked in. But nothing exactly the same length as the jacket! It looks forced and awkward.

Top Layer Option: A casual shawl provides extra warmth an makes the prim-and-proper cut of the blazer feel a little less formal. Bonus!

Styling Tip: A-line skirts and fit-and-flare dresses are just the right silhouette to balance a Coco Chanel jacket's square proportions. Pants should be exaggerated shape as well, so go for legging-like skinny or wide leg.

The Outerwear: An Slouchy Bomber

Lower Layer: Thanks to the roomy sleeves, heavier fall pieces, like chunky cable knits and wool pullovers, work. The caveat: everything must be either slightly cropped or tucked in to offset a baggy bomber's volume and cinched-in bottom.

Top Layer Option: Nothing—if it's too cold for this look, just switch to an overcoat.

Styling Tip: To make a turtleneck/pencil skirt combo a little less liberian, throw this on top. You'll instantly look Jenna Lyons cool.

The Outerwear: A Short Sleeve Coat

Lower Layer: Without the confines of sleeves to consider, this is one of the few instances where a bulkier bottom layer actually works. Or course, a thin long sleeve shirt gets the job done, too. But I say take advantage of the chance to show off your new sweaters—especially ones that don't fit under a bomber, blazer or moto jacket.

Top Layer Option: A skinny waist belt so your shape doesn't get lost beneath all those clothes.

Styling Tip: Higher necklines are better suited to the cozy, bundled up feel of this look.

The Outerwear: A Moto Jacket

Lower Layer: Tops with slim sleeves, like cotton pullovers and tissue tees.

Top Layer Option: Shrunken shearling vests, left loose.

Styling Tip: If the first layer is light enough, there should be room enough to wear the vest under your jacket as well. That means you can squeeze two different looks out of the same exact three pieces without anyone knowing.

The Outerwear: A Field Jacket

Lower Layer: Probably the most versatile of all light autumn layers, the field jacket is long and loose enough to throw over any denim/casual shirt combo. Skirt-wise, it'll always work with a mini-length, but I'd avoid anything past the knees. The longer proportions of a midi- or maxi- skirt are better suited to outerwear that hits above the hip.

Top Layer Option: Cozy fur vests work both on top of and underneath an anorak.

Styling Tip: Use the laid-back tomboy vibe to offset something a little more feminine, like Alexa Chung does.