How to wear a button-down shirt
Ocbd with a jacket, khakis and brown longwings
This look may be the most characteristic of them all and the OCBD is the heart of it. The button-down looks greater than ever and the collar rolls smoothly.
On the OCBD Jay has an unconstructed jacket. If you're not sure if your jacket is unconstructed, it's most probably constructed. Unconstructed jackets have no padding or lining, making it ultimately casual and easy-going, but still sharp. It really doesn't point you out that much, but if it does you will look a lot better than than the guys with take-off ramps on their shoulders... Jay is also rocking a pair of khaki chinos. The fit should be somewhat straight and you can roll up the legs if you wish.
A good rule is that the belt should match the shoes, it's a harmony decided by wise men a long time ago and you should only break that rule at your own risk. And finally, the pair of brown longwing bluchers make the stone foundation of this look. As you can see, all the colors are quite neutral, but as one famous fashion designer once said:
We look our best in subdued colors, sophisticated cuts and general air of sleek understatement"
White ocbd with denim and black longwings
The white OCBD stands out from this look. A White button-down shirt is easily worn with almost anything from jeans to suit and tie. It's probably the most versatile piece of clothing after your heritage underpants. And by rolling up his sleeves Jay easily brings the house down. Raw denim in this outfit gives it the sturdy and solid look. The legs look good rolled, but the real reason to pin roll them is that there's a chance for you to show off the selvedge seam. Hipsters will go green with envy before you can spell black longwing bluchers backwards!
Black longwing bluchers are like the brown ones, but black and they're freaking awesome. They're on every Ivy-enthusiasts "Things to get before I die"-list. Try finding a pair with a shell cordovan leather and you're all set. An olive tote bag is for carrying all the stuff you usually use to carry around. Jeans' pockets tend to fray, when having held a table television-size phone there for some time, so believe it or not folks, bags really have a function!