There are always exceptions. Or are there? At the very least, the following will take a long, lonnnng time to fall out of style and favor. Additions, overlooked exceptions, etc… can go in the comments. Top Photo Credit: Amy Gahran
1. Two button, center vent, navy wool suit with a medium width notch lapel
2. The bright white dress shirt
3. Semi-spread collars
4. 2.5″ – 3.25″ wide silk neckties with simple stripes or small dots
5. The Half Windsor
6. Brown (or black) cap toe, closed lacing true oxfords
7. Bar lacing (how-to here)
8. The small and subtle buckle dress belt with minimal shine
9. A silver dial, simple face dress watch with a leather band that matches your belt and shoes
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10. Peak lapel, single button tuxedo with bow tie
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11. The stainless steel dive watch (preferably one with minimal shine and medium to large width links)
12. A black, fitted polo that hits at mid bicep or just above
13. A light blue oxford cloth button down
14. Merino V-Neck sweaters in medium to light grey, navy, and black
15. Suede Chukkas / Desert Boots
16. Classic canvas sneakers
17. Slim but not tight, dark wash blue jeans
18. That dark denim with a solid light button up, a grey or blue cotton sport coat, and good looking lace ups or boots.
19. A leather billfold
20. The somewhat structured, soft sided briefcase with top centered handle(s)
21. Silver knot cufflinks
22. Or… silk knot cufflinks
23. A wool peacoat, double breasted overcoat, or single breasted top coat.
24. A water resistant trench that hits just above the knee
25 Carrying a good looking, classic umbrella, if there’s a decent chance of rain
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26. Clean shaven
27. A side part that’s not overly maintained
28. Getting your hair cut a week before people start to notice you could use a haircut
29. Dry gin martini with a lemon peel twist
30. Single malt, neat
31. Thinking carefully about whether or not you really want a third
32. Knowing when it’s time for you, or your friend to get a cab
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33. Having decent stationery on hand
34. Handwritten thank you notes
35. Giving flowers for no reason
36. Paying in Cash
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37. James Brown
38. Getting on the dance floor (even if you’re not a great dancer)
39. Taking the stairs
40. Smiling