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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: 10 White Pieces You Can Totally Wear After Labor Day

shirt dress list
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A Tee Under a Slip Dress

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

sweaterdress list
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An Ultra-fine Sweater Under a Dress

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

sweater skirt list
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A Sweater Over a Sundress

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

RELATED: The 7 Shoe Trends You’ll See Everywhere This Fall

offshoulder list
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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

cropped coat list
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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: 21 Things to Wear with Ankle Boots

sandals list
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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.

sheer skirt list
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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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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: 11 Weekday Uniforms You Can Easily Adopt

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