Q My wife and I are attending a weekend wedding in Chicago this fall. There will be a series of events besides the ceremony itself. As a groomsman, I will be dressed up for the wedding, but we were told the rest of the weekend will be informal. I’m trying to decide what to wear and my wife insists that casual duds won’t do. What does informal mean in the “big city.”
A Your wife is right to have you consider dressing somewhat less casually, especially if she intends to do so herself. Just as “you don’t need to bring anything” still means a gift would be nice, “informal” still means looking well-put-together … or it should. Time was, not too long ago, when it was considered insulting to one’s hosts not to “dress up” for a social occasion. Underdressing was thought of as a sign of disrespect and not something you did if you hoped to be invited again. These days, it seems as if very few people think that way.
I saw this reality when I was invited to a similar event early this summer. It was a very special outdoor/indoor party in honor of a milestone birthday. Everything about the perfectly planned event was unique and memorable: from the location at a former Brooklyn warehouse looking out at the Statue of Liberty, to the floating candles and fresh flowers, to the artistically arranged antipasto table on the terrace, the gourmet dinner served indoors, a DJ’s music, and dancing. These all set the evening apart from, and above, many New York Fashion Week events that I have attended.
On the other hand, what surprised (and disappointed) me were the clothes. The invitation had said that the dress would be “casual.” Even so, it was a grand party and “casual” can also be smart. I chose what to wear with care and presumed others would do the same. Not that they were dressed in a sloppy manner, but my disappointment was that I saw very little that was special, in keeping with the tone of the party, and the effort the hosts had put into it. Those who were dressed nicely were some (not all) of the women. A few wore festive-looking outfits; the rest dressed in nondescript summer attire. But, of the 30 or so men in attendance, I only recall seeing one wearing a tie and a few in sports jackets. The others wore every variation of casual Saturday-errand attire, except, thankfully, no shorts. Most dressed in standard sport shirts or open-at-the-neck dress shirts. Some shirts were good looking and well-chosen, but most were “nothing to write home about.”
To me, ignoring this opportunity to dress smartly seemed to be taking away a major element of the fun of a social evening. I don’t see why anyone would deliberately make such a choice. While it’s always confusing to figure out what to wear for special occasions, I told myself that the heavy emphasis on dressed-down, relaxed clothing was partly because it was summer, when clothes tend to be more casual than during the fall and winter.
So, as you may have gathered, I think you should dress up a bit, rather than down for these events. This is especially true as a member of the bridal party (even beyond the ceremony and party); you are something of an extension of the hosts, which calls for paying a little extra attention. And, in the fall, dressing down begins to fade with the temperature.
You would be well served to include in your packing such items as a well-cut navy blazer in wool or perhaps an ivory-colored blazer in silk, trim-fitting dark dress trousers, a pair of khakis, one white and one light blue dress shirt with a tie for each, and a handsome sport shirt in a colorful small-print or plaid. For an unexpected great look, consider a pastel-colored wool blazer. As an adult, take along a pair of quality leather dress shoes rather than deciding to compromise with today’s popular rubber-soled “dress shoes.” If some of these are not natural elements of your wardrobe and you cannot/do not want to add them, at least include what you consider your best “night out” look. This is a highlight occasion; there is no reason to wear lowlight clothing.
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