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HTML 

              
                .container
	.pumpkin-top
		.stem
	.pumpkin
		.pumpkin-middle
			.shadow-small
			.shadow-small
			.shadow-small
			.shadow-small
		.pumpkin-bottom
		.eye.left
		.eye.right
		.nose
		.mouth
			.tooth-upper
			.tooth-upper
			.tooth-lower
			.tooth-lower
			.tooth-lower
	.platform
!

CSS 

              
                $font-size: 20px; // Scale

// ===== Colors =====
$pumpkin: #e37b3b;
$pumpkinshadow: #e3631b;
$moutheyes: #1b0b1b;
$bgcolor: #7353c3;
$platform: #5f378f;
$stem: #4b9b7b;

// ===== Mixins =====

@mixin absolute-horizontal-center {
	position: absolute;
	transform: translateX(-50%);
	left: 50%;
}

@mixin absolute-vertical-center {
	position: absolute;
	transform: translateY(-50%);
	top: 50%;
}

@mixin centerAbsolute() {
	position: absolute;
	top: 50%;
	left: 50%;
	transform: translate(-50%, -50%);
}

@mixin circle($radius) {
	height: $radius;
	width: $radius;
	border-radius: 100%;
}

@mixin isosceles-triangle($height, $width, $color) {
	border-bottom: solid $height $color;
	border-left: solid ($width/2) transparent;
	border-right: solid ($width/2) transparent;
}

@mixin isosceles-triangle-upsidedown($height, $width, $color) {
	border-top: solid $height $color;
	border-left: solid ($width/2) transparent;
	border-right: solid ($width/2) transparent;
}

@mixin isosceles-triangle-pointed-right($height, $width, $color) {
	border-left: solid $height $color;
	border-top: solid ($width/2) transparent;
	border-bottom: solid ($width/2) transparent;
}

@mixin isosceles-triangle-pointed-left($height, $width, $color) {
	border-right: solid $height $color;
	border-top: solid ($width/2) transparent;
	border-bottom: solid ($width/2) transparent;
}

@mixin right-triangle($height, $width, $color) {
	border-bottom: solid $height $color;
	border-right: solid $width transparent;
}

@mixin right-triangle-pointed-left($height, $width, $color) {
	border-bottom: solid $height $color;
	border-left: solid $width transparent;
}

@mixin isosceles-trapezoid($height, $topwidth, $btmwidth, $color) {
	width: $topwidth;
	$sideCutWidth: ($btmwidth - $topwidth) / 2;
	border-bottom: solid $height $color;
	border-left: solid $sideCutWidth transparent;
	border-right: solid $sideCutWidth transparent;
}

// Styles to extend

.pseudo {
	content: '';
	position: absolute;
}

// Those little rounded shadow details
.little-shadow {
	background: $pumpkinshadow;
	width: 0.4em;
	border-radius: 0.2em;
}

// ===== Styling =====

body {
	background: $bgcolor;
	font-size: $font-size;
}

.container {
	height: 15em;
	width: 15em;
	@include centerAbsolute;
	top: 70%;
	//@include absolute-horizontal-center;
}

.pumpkin, .pumpkin-top, .stem, .platform {
	@include absolute-horizontal-center;
}

.pumpkin-top {
	background: $pumpkin;
	height: 2.5em;
	width: 10.8em;
	border-radius: 2.5em 2.5em 0 0;
	box-shadow: inset -2.5em 0em 0 0 $pumpkinshadow;
	
	// Little shadow details
	&:before, &:after {
		@extend .pseudo;
		@extend .little-shadow;
	}
	
	&:before {
		height: 0.9em;
		top: 1em;
		left: 1.7em;
	}
	
	&:after {
		height: 1em;
		border-radius: 0.2em 0.2em 0em 0em;
		top: 1.505em;
		left: 4.2em;
	}
	
	// TODO: ANIMATE!
	animation-name: raise-top;
	//animation-duration: 4s;
	
	.stem {
		background: $stem;
		height: 1.2em;
		width: 1em;
		top: -1.2em;
	}
}

.pumpkin {
	bottom: 0.6em;
	height: 11.9em;
	width: 11.8em;
	position: absolute;
	bottom: 0.6em;
	// So the angled shadow doesn't disturb the pumpkin
	// shape when the top is lifted
	overflow: hidden; 
}

.pumpkin-middle {
	//z-index: 1;
	
	@include isosceles-trapezoid(9.7em, 10.8em, 11.8em, $pumpkin);
	position: absolute;
	
	// Shadow on the side of the pumpkin
	&:before {
		@extend .pseudo;
		transform: rotate(-2.97deg);
		top: -0.07em;
		right: -0.275em;
		height: 9.9em;
		width: 2.5em;
		
		background: $pumpkinshadow;
		//background: blue;
	}
	
	// Non-shadow area around the right eye
	&:after {
		@extend .pseudo;
		background: $pumpkin;
		top: 2.5em;
		right: 1.1em;
		height: 4.4em;
		width: 1.25em;
		border-radius: 1em 0.35em 0.35em 0;
	}
	
	// Little shadows
	.shadow-small {
		@extend .little-shadow;
		position: absolute;
		
		&:nth-of-type(1) {
			border-radius: 0em 0em 0.2em 0.2em;
			height: 1.95em;
			top: 0em;
			left: 4.2em;
			
			&:before {
				@extend .pseudo;
				@extend .little-shadow;
				height: 0.55em;
				bottom: -0.75em;
			}
		}
		
		&:nth-of-type(2) {
			height: 1.7em;
			top: 6.1em;
			left: 0.4em;
			
			&:before {
				@extend .pseudo;
				@extend .little-shadow;
				height: 0.55em;
				bottom: -0.75em;
			}
		}
		
		&:nth-of-type(3) {
			height: 1.35em;
			top: 1.6em;
			left: 6.35em;
			
			&:before {
				@extend .pseudo;
				@extend .little-shadow;
				height: 0.45em;
				top: -0.65em;
			}
		}
		
		&:nth-of-type(4) {
			background: $pumpkin;
			height: 1.2em;
			left: 9.75em;
			top: 8.05em;
		}
	}
}
	
.pumpkin-bottom {
	background: $pumpkin;
	height: 2.2em;
	width: 11.8em;
	position: absolute;
	bottom: 0;
	border-radius: 0 0 18% 18% / 0 0 90% 90%;
	
	// Shadow
	box-shadow: inset -2.5em 0em 0 0 $pumpkinshadow;
	
	// Tiny detail shadow
	&:before {
		@extend .pseudo;
		@extend .little-shadow;
		height: 0.8em;
		bottom: -0.2em;
		left: 3.7em;
	}
}

// ------- Facial features -------

.eye {
	position: absolute;
	top: 3.75em;
	
	// Iris
	&:before {
		@extend .pseudo;
		height: 0.5em;
		width: 1em;
		border-radius: 1em 1em 0 0;
		background: $pumpkin;
		bottom: -2.5em;
	}
	
	// Eyebrows
	&:after {
		@extend .pseudo;
		background: $pumpkinshadow;
		height: 3.5em;
		width: 0.6em;
		border-radius: 0.3em;
	}
	
	// Left eye
	&.left {
		@include right-triangle(2.5em, 2.5em, $moutheyes);
		left: 2.2em;
		
		&:before { left: 0.45em; } // Iris
		
		// Left eyebrow
		&:after {
			left: 1em;
			bottom: -1.8em;
			transform: rotate(-45deg);
		}
	}
	
	&.right {
		@include right-triangle-pointed-left(2.5em, 2.5em, $moutheyes);
		right: 2.2em;
		
		&:before { right: 0.45em; } // Iris
		
		// Right eyebrow
		&:after {
			//background: transparent; // TODO
			height: 4.0em;
			right: 0.8em;
			bottom: -1.7em;
			transform: rotate(45deg);
		}
	}
	
}

.nose {
	@include isosceles-triangle(1em, 1em, $moutheyes);
	@include absolute-horizontal-center;
	bottom: 5.65em;
}

.mouth {
	width: 7.5em;
	height: 3em;
	background: $moutheyes;
	border-radius: 0 0 30% 30% / 0 0 75% 75%;
	@include absolute-horizontal-center;
	bottom: 2em;
}

.tooth-upper {
	position: absolute;
	@include isosceles-triangle-upsidedown(1.3em, 1.4em, $pumpkin);
	
	&:nth-of-type(1) { left: 1.7em; }
	&:nth-of-type(2) { left: 4.25em; }
}

.tooth-lower {
	position: absolute;
	bottom: 0em;
	@include isosceles-triangle(1em, 1.2em, $pumpkin);
	
	&:nth-of-type(3) { left: 1.8em; }
	&:nth-of-type(4) { left: 3.05em; }
	&:nth-of-type(5) { left: 4.35em; }
}

.platform {
	height: 0.6em;
	width: 90%;
	position: absolute;
	bottom: 0;
	background: $platform;
	border-radius: 0.3em;
}
!

JS 

              
                // ¯\_(ツ)_/¯
!
999px

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