Dressing Better Vol 2.0

1. Please stop buying black dress pants.

Just stop it. Right now. Unless you’re a classical musician or a waiter there’s really no need to go there.

2. Assess your needs.

First, learn how people in your office dress and what the official stance on business attire is (if there is one). Some easy questions to ask yourself: does everyone have their pants creased or are they unpressed? Do you see wool slacks or cotton chinos or denim? If your office is anything like mine then all of these are perfectly acceptable, leaving the decisions to you. In my mind, business casual pants fall into three broad categories:

“Trousers.” This is a bit of a catch-all term, but in my mind it signifies pants made from a dressy fabric (usually some weave of wool, but any fiber will do) and with creases running up the legs. They will also have more formal details like slanted pockets, buttoned back pockets and hidden seams. These would be the equivalent of the bottom half of your suit, but without a matching jacket (you have a suit, right?).
Chinos. Named after the twill fabric that they are usually manufactured from, these bad boys are casual in nature but have become perfectly acceptable in most offices. These feature external stiching, rugged fabric, and a lack of creasing (or any pressing).
Denim. Now before you get too excited, this isn’t a free pass for jeans in the office. I’m talking about dark, unadorned, slim/straight denim with no rips and holes. When done right this can work well with casual fabrics like oxford cloth and tweed.
Once you figure out what your office’s feel is and where your personal tastes lie you can start looking to purchase. Try to keep things consistent with the rest of your outfit; if you wear spread collars, ties and blazers you’re going to need trousers for just about every day. If you wear button down oxford shirts, sweaters, and loafers then you can roll with just chinos and denim.

3. Figure out how these things should fit.

Now, this will depend on several things, namely your body shape, the pant style and your personal preferences. Much like shirts, the general concept is to find something that flatters your shape without pulling or looking constrictive. However, I believe that the fit should vary between the type of pants.

Trousers: due to their formal nature, I tend to lean towards classic proportions here. The nicer fabric will allow them to drape in an attractive manner and this is lost when they become overly snug. I don’t wear trousers tapered past 8” and I look for a rise that will allow them to sit above my hips.
As the intermediate choice, chinos can land anywhere on the spectrum. I prefer to keep mine on the slim side but make sure that my legs aren’t tapered past 7.5-8” (and I’m a lanky guy).
Denim can be worn slimmer than the other two styles, but within reason. I keep my denim snug in the thigh and waist as it tends to stretch with wear. I usually have a taper of about 7.5”.
Learning what pant fit suits you best will take some time and experimentation, but at the very least be conscious of the choices you make in this area so you can adjust in the future if need be. More information on fit can be found here and here.

4. Gray, gray, gray, and then something close to gray (but still not black).

Gray is a great (gray-t?) color for trousers because it provides a solid foundation for the rest of your outfit without detracting from it. It’s hard to think of a traditional shirt or blazer color that won’t look good with gray pants (with the exception of gray, of course). Embrace the color and make it the cornerstone of your collection; your brown, tan and navy blazers will thank you. Add variety by using different shades and fabrics. Of course, denim is best in navy and chinos are classic in khaki, but stick with gray trousers until you’re well on your way to a full wardrobe.

5. Experiment with materials and texture rather than colors.

Wild colors can be fun but I find that diversifying with different fabrics is a more versatile way to expand your daily choices. Worsted wool is a standby for trousers, but consider flannel, tweed, moleskin, linen, tropical wool or cotton canvas depending on your climate.

6. Pleats: the ultimate divider

Pleats got a bad reputation when they became the go-to for guys giving PowerPoint presentations. I grew up in a world of relaxed fit triple-pleat Dockers and it was not pretty. However, there is a time and place for pleats. When worn correctly (up on your hips and not pulled open) they can help create a smoother appearance of the lines in your pants, especially for men with larger seats and thighs. However, if you don’t know much about how pleats operate I would suggest avoiding them until you know if they’ll be beneficial to you. More information can be found here.

7. Break it up.

The break of a pant leg is a crucial but often ignored aspect of fit. The term “break” refers to how far the pants extend down your leg before ending. A “full break” will involve the pant leg folding upon itself several times over the shoe, whereas no break implies that the pants end before even touching your feet. A medium break is an easy choice, but current trends favor slight/no break (as do I). Narrower pant legs will look best a bit shorter, and vice versa. More information here and here.

8. Care for your clothes.

Take care of your clothes. Trousers should be hung and aired out before thrown in a closet. Dry clean only and do it as little as necessary. Chinos can usually be washed in a machine, and I prefer to hang dry mine. Iron if needed. Denim should stay out of the dryer and washed infrequently; the specifics beyond that vary depending on who you ask.

9. Make a list and stock up.

Pants for work can be found almost anywhere, but here is a short list (not complete by any means) that may help narrow your search.

Trousers: Howard Yount, Epaulet, Brooks Brothers, Land’s End

Chinos: Epaulet, Bonobos, J. Crew, Land’s End Canvas, Ralph Lauren

Denim: Levi’s, Bonobos, 3Sixteen, A.P.C.

Hope I did it right