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There are a few weeks during the months of September and October that are supremely awkward to dress for. Depending on the time of day, it’s either slightly too chilly or slightly too warm—and for some inexplicable reason certain summer staples (like that strappy sundress or pair of sandals) just feel wrong. This year, we’re taking cues from fashionable ladies everywhere and learning how to work a cross-season combo.

RELATED: Summer’s Most Popular Skirt Will Still Be Everywhere This Fall

a tee under slip dress layer summer and fall pieces
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1. A Tee Under a Slip Dress

Get an extra few months of wear out of your slinky dresses with a lightweight shirt underneath.

An Ultra fine Sweater Under a Dress layer summer and fall pieces
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2. An Ultra-fine Sweater Under a Dress

This also works well with a delicate knit (and a pair of tights in the winter).

sweater over sundress layer summer and fall pieces
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3. A Sweater Over a Sundress

Fake the look of a skirt with a chunky knit on top.

RELATED: A Discerning Editor Just Found *the* Booties for Fall 2019

An Off the Shoulder Tunic Over Wool Suiting Trousers layer summer and fall pieces
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4. An Off-the-Shoulder Tunic Over Wool Suiting Trousers

Just enough skin to keep you cool and just enough fabric to keep you covered. Have a jacket on hand for additional shoulder-draping.

RELATED: 7 Chic Off-the-Shoulder Blouses and How to Wear Them

A Cropped Jacket Over a Maxi Dress layer summer and fall pieces
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5. A Cropped Jacket Over a Maxi Dress

Fancy heeled booties are optional, but we assure you this works just as well with any pair of (ahem, more comfortable) ankle boots.

RELATED: How to Wear Ankle Boots (You Might Be Doing It Wrong)

strappy sandals with slacks layer summer and fall pieces
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6. Strappy Sandals With Slacks

Don’t put away those gladiators just yet. Worn with sensible slacks and a blouse, they no longer feel out of season.

A Sheer Maxi Skirt With a Long Blazer summer layer summer and fall pieces
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7. A Sheer Maxi Skirt With a Long Blazer

The bohemian bottom creates a nice counter to the preppy vibe up top.

duster coat list
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8. A Duster Coat Over Everything

Short hemlines, strappy heels and even our beloved off-the-shoulder tops can all be worn with a solid topper. Go with an on-trend, mid-calf length and you’ll essentially double your wardrobe.

RELATED: 10 “Boring” Fashion Basics Every Woman Needs to Own

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