Chicago Manual of Style—4/29/2011

What to wear, when and where

By Jessen O'Brien

It’s great if you have the perfect outfit for every occasion, but how you do dress when you’re unsure about the occasion? In more concrete terms, what do you wear to an event that does not specify its formality, or does so with that ever cryptic phrase, “semi-formal?” Here are some tips on how to dress for several occasions at once.

Unless you are in New York or a similarly casual city, ditch the jeans. Unless you want to go full out fashionista in them and wear a statement outfit, jeans are inherently informal. Similarly, you want to steer clear of fishnets on your legs, hair bands on your arms, and baseball caps on your head. No t-shirts, and nothing with a logo or name emblazoned all over it unless it’s the type of company that would appear in Vogue. Even in summer, avoid shorts. And, in winter, avoid a tunic and leggings. Finally, no tennis shoes or flip-flops. All of these items place you distinctly in the casual category instead of balancing on the border of formal, which is exactly where you want to be.

For men, it’s easy to throw on khakis and a polo or a button down and go either way. After all, both of those outfits could conceivably be casual or formal. For women, it’s a little more complicated. I recommend investing in a pair of black pants. As long as they are not jeans and not cutting off your circulation, black pants are wonderful because you can wear them to class or the opera. Alternatively, it’s hard to go wrong with a black skirt (or dress; there’s a reason the Little Black Dress is such a ubiquitous article of clothing) and tights, although here you have the quandaries of how short is too short and whether or not you can get away with bare legs. For length, I’d go with mid-thigh when standing. As for tights in those tricky seasons of spring and fall, I’d err on the side of tights.

Next, what to wear on top. As a soft rule, avoid cotton. If you do, almost anything else is at your disposal as long as it’s not too sexy. You can wear colors, patterns, short sleeved, long sleeved, whatever; as long as it’s paired with a more classic bottom. Avoid anything too dressy, like a stiff, collared button down, and you won’t stray on the side of too formal or suit-like.

If you do not already own a pair of nice black boots, buy some. Like black pants, black boots are simply invaluable. You can get away with some hardware as long as the boots themselves aren’t too scuffed up. Instead of bothering with heels, you can always throw on boots and be confident that they walk the semi-casual line, especially in Chicago or any other city with a cold climate.

My main and final tip, even if you ignore everything else: layers and accessories. A cardigan or scarf can transform a look. If you’re wearing a blazer, throw on a bright scarf with an interesting print. If you arrive only to find that people look more casual, keep the scarf on—you’ve successfully toned down your look while keeping it stylish. If everyone looks formal, you can just take off the scarf with your coat or even tie it around your purse. You can do the same with jewelry or a hat and alter the formality of your outfit in a mere minute. Follow these tips, and you’ll be appropriately dressed for any event.