Holiday season is officially on, and that means you're going to end up in a number of quasi-social gatherings where your attendance is underscored with a subtext of obligation. I'm talking about the likes of the annual company holiday party, the schmooze fest at the big boss's suburban McMansion, or meeting your sweetheart's family for the first time at her parents' home.
Of course, those events can be delightful, but scratch just below the surface and there's often a sense of slight uneasiness in that you know that this isn't the type of party that you can let it all loose. Unlike the parties that you voluntarily prefer swinging in, this is no place for faux pas of any kind. In fact, this is an occasion to put yourself in the best possible light in the eyes of your colleagues, superiors, and possible future in-laws. So while I can't help you from making an ass of yourself, at least I can attempt to help you avoid looking like one.
Let's start with an example of how not to dress. In all honestly, there's exactly nothing devastatingly wrong about this look. He's rocking a pop of festive color and pattern on his tie, and the windowpane blazer adds another element of textural interest — even the fit isn't all that bad. It's not that anything's blatantly wrong with him, it's just that he's just so-so, boring, standard, and exhibits no style or personality. Although not offensive, he's surely not impressive. This is not the way to go if you want to leave a memorable mark.
To amp his style, he can start by switching up the fat silk tie to a colorful knitted or woven wool one that's slightly more narrow than the one he has on — about 3" at the widest point (2 3/4" for a bit slimmer). Another easy fix is to take up the jacket sleeve so that he has about 1/2" of cuff showing when his arm is hanging straight down. Those details alone should help.
Alternatively, he can pair a solid or subtly patterned wool tie with a cheerfully colored shirt in a pattern, topped with a navy blazer (shown above). Since these occasions are a bit more relaxed, you can optionally wear a button-down collar for a more casual vibe. And if you really want to leave an impression, do like Mad Men and embellish with a simple tie bar and flash a sliver of white pocket square. A clean, super dark pair of slim straight leg jeans offer a more modern and sophisticated option to chinos, although chinos or grey wool pants that are well tailored, cut slim and with a short-to-no break will elevate you just as well. Lastly, polish off your look with a pair of brown leather-soled wingtips — they add much more smarts and interest to your look than plain black shoes.
This is a type of function where you want to stand apart from the cubicle drones, or, for that matter, loser ex-boyfriends your lady friend has brought home in past years. While it's imperative to leave a distinctively confident mark, you also need to make sure you don't come across as a dandy. Keeping all of your wardrobe components simple and classic while maintaining a modern fit and sensibility is a surefire way to make a stylish, respectable, and memorable impression.
And for the season, a distinctive but subtle conversational accessory like a pair of holiday-themed cuff links will add just the right dose of holiday flair that's sure to be appreciated with cheer.
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