We started this series with shirt advice, so now let's move down to the pants. We'll assume you already have serviceable chinos/khakis in your wardrobe. Those are great for everyday casual or dressed-down office wear, but it's time to add another basic that can be dressed-up more than chinos: gray wool trousers.
Like chinos, gray wool slacks are highly versatile. While there are many situations where chinos or gray wool slacks could be worn equally well, chinos also occupy the more casual end of the spectrum (t-shirts) while gray wool serves the more formal end (coat and tie). Thus, with these two types of pants in your closet you will have every situation short of "suit required" covered.
Now, there are some US climates where one medium-weight pair of gray wool slacks will suffice. The Midwest is not one of those places. Our extremes of heat and cold mean that you will actually want to obtain two pairs of gray wool slacks: a lighter summer-weight pair (look for "tropical weight" wool) and a heavier winter-weight pair (flannel is good here). Color-wise, we would recommend a deeper charcoal shade of gray for the winter pair and a lighter shade for the summer pair.
While we're on the topic of pants, here are a few pointers to keep in mind when shopping for them. Plain-front trousers are the standard these days. If you really want to go with pleats, try to stick with a single pleat and as trim a look as you can find. Pleated slacks should be worn higher than plain-front pants: this is how pleated slacks are designed and will help keep the pleats from puffing out. The general rule of thumb is cuffs with pleats and plain hems with plain front trousers, although the weight of cuffs can help maintain a good line on any pair of pants. When you're having your slacks cuffed or hemmed, you'll need to tell the tailor how much break you want, which determines how much of your shoe is covered by the slacks and how much extra fabric bunches at the bottom. You'll probably want to ask for a slight (quarter) or medium (half) break. No break is a popular look in some quarters these days, but will definitely attract attention in the Midwest. Whatever you do, avoid the full break, which can look sloppy. (Remember this when selecting the length of pre-finished pants, as well.)
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