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 on the stereo

38. Getting on the dance floor (even if you’re not a great dancer)

39. Taking the stairs

40. Smiling