Santa's Little Helper: Dressing Him for the Holidays

lay it out for him.

lay it out for him.

November is marching along, which can only mean one thing: the holidays are almost here! This signifies a lot of things for a lot of people: spending time with family and loved ones, appreciating life’s blessings, and preparing for a new year of opportunity and growth. That’s all well and good, but the holidays also mean parties. Even if it’s just to your mother’s house for eggnog and cookies on Christmas morning, we’re willing to bet you’ll be invited somewhere you’ll be expected to wear decent clothes and socialize with other human beings.

If you have a significant mister in your life during this festive season, chances are A) he’s going to be attending these parties with you, and B) you’re going to want him to look good when he’s on your arm. While the idea that “men don’t care about fashion” has long been disproven (check out meninthistown if you require proof of this claim), what if your beau just can’t tell the difference between a placket and a jacket? Or what if his idea of “dressing up” consists of donning black Rainbows instead of his usual classic brown? If this sounds like that special man in your life, then it seems you have two people to dress for this year’s festivities. There are three major types of situations that you should be prepared to tackle:


We’re not necessarily referring to a situation where tuxedos and evening dresses are required (although you should keep an eye out for the words “black tie”- the host is asking for a very specific type of formalwear and it’s considered rude not to comply with that request). An example of this type of situation might be a dinner or event your boss hosts. You’ll be trying to maintain some semblance of professionalism, so you’ll want him to be on the same page. If you’re wearing a dress and heels, putting him in a slim three-piece suit would be a smart route to take, like this Navy Twill Photographer Suit from ExpressMen. Navy, which is a flattering color for all skin tones, is versatile and quietly sophisticated, and can be matched with a variety of colors. If the tone of the event is more relaxed, you can play around with different pieces. Perhaps ditch the vest and switch out the solid button-up for one in plaid to achieve a nice contrast between modern lines and a classic print, or pair the suit with burgundy dress shoes for an added pop of color. Don’t forget the tie!


Think: family party hosted at a relative’s home. It’s a much more relaxed atmosphere, but you’ll still want him to make a good impression among company of mixed age and gender, especially if this is the first time you’re bringing him around to meet everyone. A suit isn’t necessary, and jeans and a t-shirt aren’t appropriate, but pairing a blazer with slim-fit denim in a dark wash over a knit sweater might bring together the best of both worlds. A pair of well-fitting chinos in a neutral color like beige or brown, such as these 1901 ‘Ottoman’ Slim Fit Pants, is the epitome of the sophisticated-yet-easygoing look you’ll want him to be sporting here. Pair them with a knit pullover or shawl collar cardigan over a button-down to complete this look.


This type of situation would probably involve going to a friend’s house for a night of good ol’ fashioned debauchery. The other people in attendance will most likely be your friends and acquaintances, in which case you’ll probably just want to let him dress in the style that feels most natural for him. Jeans and a t-shirt would definitely be appropriate here if that’s your guy’s standard go-to outfit, unless there’s a theme like “ugly sweater” or what-have-you. Just remind him that it’ll most likely be chilly outside, so he’ll want to take a jacket with him (which you’ve already picked out, obviously).

Of course, the situations described above are completely dependent on your personal situation. Your boss might take the office to a dive bar for happy hour and call it a Christmas party, and your mom might hold her annual New Year’s celebration at a country club this year. You know your work environment, your family and your friends better than we do, after all. If you stay flexible and stay clever, you and your boy will surely be the belles of every ball you attend this holiday season.

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