Pencil Skirts & Pantyhose: Businesswear Decoded

For men in an office environment, you pretty much have three levels of formality: A full suit with a tie is business formal, without the jacket or tie is business casual. Throw in a few pairs of khakis and the occasional polo on a Friday, and a dude is good to go.

For more feminine profiles, what to wear can be a little tougher to decode. When are pantyhose appropriate? When should you wear a blazer? When are heels essential, and when is it better to wear flats? With a few easy tricks to remember, you’ll soon be feeling more comfortable in front of your closet on the day of your next important business meeting even if you usually never change out of jeans and Chucks.

Think of businesswear like an upside-down pyramid. At the top, you have outfits that include everything: Blazer, crisp shirt, skirt or pants, pantyhose (if you’re wearing a skirt), and heels. This is for the most formal of business days: When you’re giving a presentation, for example, or the day of an important event. In some industries this full-regalia outfit will be more common, like administration, politics, law or the financial sector. Other industries will rarely see this in the office – creative fields and newer tech companies are usually more casual.

The next level down means taking off a few of these components. You won’t need the blazer or pantyhose, and you can probably choose nice flats if you prefer. You can also wear bolder colors and jewelry. This type of outfit would be for a regular day in a more formal office, or a meeting day in an office that usually allows jeans. A less-formal business casual would allow even khakis or a less-formal blouse.

Then there’s the jeans office, which can be tricky to think about when you first encounter it. You wore jeans to every day of high school, so you should be fine, right? Yes, as long as you keep in mind that a professional look never involves torn knees – not even for a “distressed” look. Jeans should be a dark wash, as it’s more formal than fades or washes. They should be slim but not tight and paired with a nice top, not a message t-shirt. Flats or boots are probably the best shoes for a jeans office, not sneakers. There may be an office out there that allows Chucks, but you might want to check with your supervisor first.

There are a few pitfalls to watch out for in a new office, especially if dress rules are strictly enforced. In warmer climates, sandals are an essential part of staying cool, but in other areas it can be considered too informal for a business-casual office. This is nice sandals, like an open-toe wedge — don’t wear flip flops to the office unless you’re a lifeguard or you get allowance in writing. Some other common clothing concerns from management are clothes that are too revealing, distracting colors or patterns, powerful perfumes, or big flashy jewelry. Check with a friend in the office before coming to the office in an outfit you’re not sure about. It can seem silly to ask, but it’s better than getting unwanted attention from you manager for something that has nothing to do with your work.

Whether your office is formal or allows pajamas will depend a lot on your industry, your company, and your level of seniority. If you’re worried about what to wear on your first day, err on the side of being too formal rather than too casual. And when in doubt, you can really never, ever go wrong with a pencil skirt.

Featured image via Shutterstock