No One Has Swagger Like These Four Guys

Although I hate the word 'swag' (and every form of it), these dudes do have swag.
Word of advice: a classic leather bomber, a long scarf (not the ones I hate), a peacoat, investing in some sturdy denim, sneakers that aren't necessarily Nike or any other well known brand, European-inspired boots, Argyle, beanies, and oxford shirts are standard pieces that should be in every man's wardrobe.