Oh no. Here it goes again. You have just been asked to chaperone a family member to a date. You know you're not supposed to interfere, or to look too conspicuous either. For the latter, you need to dress incognito in order to watch over the entire thing while pretending you're not there.
Dressing up as the chaperone isn't so hard. As the representative of the parents, you don't have to look like a parent yourself. They key is to identify the dress code for the particular venue where the appointment would take place.
In a fancy restaurant, of course you should look decent, but not too attractive that you're sibling's or cousin's partner would be drooling all over you. Try to appear more casual then those going on a date themselves; avoid looking like you're the one out on date by ignoring patterned or shiny clothing.
Wear a long-sleeved shirt without a tie, with the top three buttons informally unclosed. Or you can wear a dark-colored polo shirt. If it's cold, bring a leather jacket with you to impress the kids. Your trousers, naturally, should be pressed and in either navy, dark gray, or black. Espadrilles or clean sneakers can be worn.
On a date out on a regular eat-out place, wear a tee that's not solid-colored. A V-neck short-sleeve in gray points out that you're the authority in the gathering. You can also choose a tee with an interesting print or design. Just don't wear something that is too tight. You certainly know better that you can't put on a t-shirt that has shows off rated-R graphic or text. The pants you pair your shirt with could be baggy with many pockets, or plain dark blue denim jeans. Sandals aren't restricted either.
When in a by-the-beach place, you're forgiven if you're wearing Hawaiian flower-prints and open shoes. Just don't overdo with khaki shorts and a ring of flowers around your neck. The sandals don't have to be any other color apart from brown. As for accessories, a watch to tell the time is always indispensable. Don't wear stud if you've got piercings.
The most useful tip you can follow when you want to dress well as a chaperone is go with what the younger ones are wearing. Of course they hate you for being the eye in the sky, but they'll hate you less when you don't embarrass them unintentionally.
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