An orange plaid short sleeve shirt and navy jeans are true menswear staples if you're planning an off-duty wardrobe that holds to the highest style standards. Ramp up this whole outfit with a pair of black fringe leather loafers. This ensemble is the definition of ideal for hot summertime afternoons. Those who are curious how to wear classic and casual outfits as you go through your 20s, this combination should answer your question.