<div class='content-container'>

    <div class='madeby-grid'>

        <div class='madeby-grid__item'>

            <div class="madeby-grid__image">
                <img src="https://source.unsplash.com/random/1600x900" alt="">
            </div>

            <div class="madeby-grid__content">
                <h3>Your Name</h3>
                <p>Product: Defender Extreme<br>
                Customer Name: Company Name<br>
                Installed for: Cineword, Middlesbrough</p>
            </div>
            
        </div>

        <div class='madeby-grid__item'>

            <div class="madeby-grid__image">
                <img src="https://source.unsplash.com/random/900x900" alt="">
            </div>

            <div class="madeby-grid__content">
                <h3>Your Name</h3>
                <p>Product: Defender Extreme<br>
                Customer Name: Company Name<br>
                Installed for: Cineword, Middlesbrough</p>
            </div>

        </div>

        <div class='madeby-grid__item'>

            <div class="madeby-grid__image">
                <img src="https://source.unsplash.com/random/900x1600" alt="">
            </div>

            <div class="madeby-grid__content">
                <h3>Your Name</h3>
                <p>Product: Defender Extreme<br>
                Customer Name: Company Name<br>
                Installed for: Cineword, Middlesbrough</p>
            </div>

        </div>

        <div class='madeby-grid__item'>

            <div class="madeby-grid__image">
                <img src="https://source.unsplash.com/random/1601x901" alt="">
            </div>

            <div class="madeby-grid__content">
                <h3>Your Name</h3>
                <p>Product: Defender Extreme<br>
                Customer Name: Company Name<br>
                Installed for: Cineword, Middlesbrough</p>
            </div>
            
        </div>

        <div class='madeby-grid__item'>

            <div class="madeby-grid__image">
                <img src="https://source.unsplash.com/random/901x1601" alt="">
            </div>

            <div class="madeby-grid__content">
                <h3>Your Name</h3>
                <p>Product: Defender Extreme<br>
                Customer Name: Company Name<br>
                Installed for: Cineword, Middlesbrough</p>
            </div>

        </div>

        <div class='madeby-grid__item'>

            <div class="madeby-grid__image">
                <img src="https://source.unsplash.com/random/901x901" alt="">
            </div>

            <div class="madeby-grid__content">
                <h3>Your Name</h3>
                <p>Product: Defender Extreme<br>
                Customer Name: Company Name<br>
                Installed for: Cineword, Middlesbrough</p>
            </div>

        </div>

        <div class='madeby-grid__item'>

            <div class="madeby-grid__image">
                <img src="https://source.unsplash.com/random/1602x902" alt="">
            </div>

            <div class="madeby-grid__content">
                <h3>Your Name</h3>
                <p>Product: Defender Extreme<br>
                Customer Name: Company Name<br>
                Installed for: Cineword, Middlesbrough</p>
            </div>
            
        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

        <div class='madeby-grid__item'>

        </div>

    </div>

</div>
*,
*::before,
*::after {
	box-sizing: border-box;
}

body {
	padding: 1.618rem;
}

.content-container {
	text-align: center;
}

.madeby-grid {
	display: grid;
	grid-template-columns: repeat(auto-fill, minmax(20rem, 1fr));
	grid-auto-flow: dense;
	grid-gap: 1.618rem;
	max-width: 1440px;
	margin: 0 auto;	
}

.madeby-grid__item {
	padding: 1.618rem;
	border: 1px solid;
	min-height: calc(1.618rem * 5);
	grid-row-end: span 3;
	
	display: flex;
	flex-direction: column;
	height: 100%;

	img {
		width: 100%;
		height: auto;
	}
	
	&.landscape {
		grid-row-end: span 3;
	}
	
	&.portrait {
		grid-row-end: span 5;
	}
	
	&.square {
		grid-row-end: span 4;
	}
	
}

.madeby-grid__content {
	display: flex;
	height: 100%;
	flex-direction: column;
	justify-content: center;
}
View Compiled
$( window ).on( "load", function() {

	$('.madeby-grid__item').each(function() {

		var item = $(this);

		var width = item.find('.madeby-grid__image img').outerWidth();
		var height = item.find('.madeby-grid__image img').outerHeight();

		if( width > height ) {

			item.addClass('landscape');

		} else if( height > width ) {

			item.addClass('portrait');

		} else {

			item.addClass('square');

		}

	});
	
});

External CSS

This Pen doesn't use any external CSS resources.

External JavaScript

  1. https://cdnjs.cloudflare.com/ajax/libs/jquery/3.2.1/jquery.min.js