These days Uncle Sassy works in a big corporate office with lots and lots of people. After years on the job I’ve finally figured out the difference between the guys who are “on the track” vs. the “guy in IT” – it’s their clothes. If you want to play with the big boys, you gotta dress the part – and I’m gonna tell you how.

Most offices these days are “Business Casual” – meaning you don’t wear a suit. But even without the tie and jacket, you still can look sharp for that impromptu meeting with the CEO. Like it or not, you are judged on your appearance – and there is a world of difference between a true player and the khaki-clad, polo-shirted cube jockey.

Pants
When you walk into Macy’s, you will see a big selection of men’s clothing right near the entrance. Walk right past this section and find the place where the suits are sold. The section out on the floor is the casual section. Those clothes are meant for 25-year olds with their parent’s credit cards. If you want nice clothes for work, you need to find the old man with a tape measure around his neck, usually in the back with all the suits.

A good pair of Italian 100% wool slacks should last you nearly a lifetime with care. Avoid elastic waistbands, stretch, or polyester. If you are under the age of 40 and in decent shape you should consider flat-front pants. Pleats are fine for those of us with a bit of a spare tire to cover up. Wear your pants at the waist and wear pants that fit. There is no level of bagginess or sag that is appropriate in the office. Low-rise pants for men are an abomination and should never be worn to work.

Get your pants hemmed by a tailor. The break of your hem (how much your pants rumple at the shoe) is crucial. Short men can wear pants hemmed with no break or a half break. Tall men should wear a full break. A proper hem is to the heel of your shoe and to about the third lace of the shoe’s upper. Be careful about pants that are too long and fold over too much – and watch out for too-short hems, these are very common problems I see in the young men around my office. Also avoid the “straight leg” look – your pants will cover too much of your shoe. Cuffed pants are generally out of fashion for younger men.

Keep your pants pressed. Creased fronts are more dressy than plain fronts. Chinos and Khakis are OK too, but if you want to be “on the track”, save em’ for casual Fridays.

Shirts
Remember when I was talking about the casual section? Try this sometime: go look at a button-down shirt in the casual section and check the size. Then, go to the dress shirts and check their sizes. You’ll notice that the casual shirts are sized “Small” or “Large” while the dress shirts are “16 – 34/35” or whatever.

Ask the old guy to measure you for a shirt and buy the shirt that fits. Those casual shirts will never fit right and will always have some problem like too-short sleeves or collars that are too wide. You can buy the “slim fit” shirts if you’d like but you’d better be slim.

Personally I stick to 100% Italian cotton shirts – no stretch, no sateen, no permanent press. French Cuffs are for bankers and salesman, otherwise it’s a bit dressy for most offices – but if you like em’, go for it. Grandpa’s cufflinks are classier than Geoffrey Beene’s.
Iron and starch your shirts every time you wear them. Your sleeves should have crisp creases. Press your collars – I can’t tell you how many men I see with curled collars.

Personally I do not like button-down collars. Also, a men’s dress shirt has a breast pocket. If the shirt doesn’t have a breast pocket, it’s for the clubs, not work. Keep your shirt buttoned to the top if you wear a tie, otherwise the top button is the only one that should be undone.
Long-sleeves are the safest bet if you want to look sharp. Polo shirts, short sleeves, untucked shirts are OK on casual fridays but otherwise should be avoided.

Shoes
Shoes make the man and they are the easiest way to tell a player from a schlub. Those thick-rubber-soled square-toed shoes that Steve Madden is churning out of Malaysia are cheap and look cheap. If you can afford it, buy Italian leather shoes with sewn (not glued) leather soles. It’s tough to swallow spending 300 bucks on a pair of shoes but with care they will last you for life. Those glued rubber sole shoes will fall apart in 3 years. Keep em’ shined.

Avoid trendy shoes at all costs. Those gauchos or alligator skinned mocs are not gonna fly. Oxfords, pennies, weave loafers – stick to the classics. Besides, when those goofy shoes go out of style in 3 years you’ll still be looking sharp.

Socks, Belts, Jewelry
Dress socks are key – no ribbed black cotton jobs allowed. Your belt should be conservative – avoid chromed or large buckles. Jewelry should be similarly conservative – those gigantic men’s watches are great if you work for a record label but ain’t gonna fly at a real job. Similarly, those wristband watches are better for the weekend.

Grooming
Unfortunately for Uncle Sassy, who loved his mop-top and goatee, short hair and clean-shaven is the way to go. That means no sideburns either. Neat and clean nails, teeth, it all matters.

So that’s it kiddies.  Get that credit card warmed up and make it happen.  You’d be surprised how much more seriously people take your nonsensical ramblings when you look good.