<div class="item-image">
            <div class="plus-wrapper">
                <div class="plus"></div>
                <img src="source_to_image" alt="">
            </div>
        </div>

var image = $('.plus-wrapper img');
        image.each(function () {
            var that = $(this);
            if (that.width() < 250) {
                that.next('.plus').css('right', '41px');
            }
        });

$(window).load(function(){
    var image = $('.plus-wrapper img');
        image.each(function () {
            var that = $(this);
            if (this.width < 250) {
                that.prev().css('right', '41px');
            }
        });
});

var image = $('.plus-wrapper img');
    image.each(function () {
        if ($(this).width() < 250) {
            $(this).siblings('.plus').css({'right' : '41px'});
        }
    });