When it comes to the question of “What to wear” for Holiday Events, simple elegance is your best solution. Whether your personal style is Streetwear or Classic Menswear; for a family gathering, your girlfriend's office party, a formal gala or a dinner with friends, it's not hard to be comfortable, to enjoy yourself and to look your very best all at once.
Start with the basics: a dark suit or blazer, a crisp white shirt, great shoes (well polished black ones for evening) and please, this Christmas, leave irony to the insecure and to Urban Outfitters. Do you want to be remembered for being well-dressed or for having a silly tie?
My guideline that applies especially to dressing for the Holidays is the “One Rule." People will notice any one special item you are wearing, but their attention becomes diverted by multiple statement pieces of clothing or accessories. More isn’t better, more doesn’t make you “better dressed." In fact, it distracts so that nothing is remembered other than that your outfit looked busy - or that you're trying too hard. Limit yourself to one article of clothing or accessory that expresses your festive mood. Wear it well and enjoy it.
Your wardrobe basics are ideal for Holiday events. However, consider getting something special this year to wear and enjoy throughout the season and for future Holiday occasions. For example, if you entertain at home, a pair of velvet slippers makes even a pair of flannels and a sweater seem special. My wife special-ordered a pair for me with my initials one year and they have become an enjoyable Holiday tradition. Many companies offer these, including Foster & Sons custom monogrammed slippers from The Hanger Project, while ready-to-wear versions from Stubbs & Wootton or Shipton & Heneage offer everything from plain velvet to fun and elaborate embroidered themes reflecting your interests, university or attitude.
If you already have a dark suit or navy blazer, consider a velvet jacket. You know those invitations marked “Dress: Festive Holiday Attire”? A velvet jacket certainly qualifies. A velvet jacket is like champagne; it makes any occasion just a bit more special and fun. And, women will want to touch you. I wear mine with a casual mix of jeans, and a white shirt for a lunch or dinner at home with friends and with a black bow tie, white shirt and flannels for almost any semi-formal evening event. (No need for those bright red Reindeer socks; the velvet says it all). Ralph Lauren and Paul Stuart are often good sources for velvet jackets but most better menswear retailers offer them as made to order.
If your personal style is a bit more artistic or modern consider charcoal pants, black shoes and a great fitting, special white shirt. It always looks smart and the focus is on the subtlety of the fit, cut and style of your clothing. Want to kick it up a notch? Get something a bit architectural or decorative from a designer like Comme des Garçons.
Drake's tie; 155$ at Sid Mashburn
Don’t be concerned about being a bit overdressed. Pull out that dark suit, simple dark tie, white shirt, white pocket square and black shoes and you will not only look well-put-together, you’ll look dashing in a Bond-ish sort of way. No need for a bright red pocket square (which too often look like cheap lingerie anyway), as the classics will do you just fine. No dark suit? Grey flannels and a blue blazer will work fine. If you want add a little Holiday color, how about a classic tartan plaid tie to wear with that white shirt and blazer? I personally like the more subtle green and blue Black Watch Plaid, such as this one from Drakes.
Traditional formal is rare in most circles but don’t let that stop you from enjoying black tie. After all, every guy looks great in a dinner jacket. Depending upon the event and the crowd, you may want to stick with a classic tux, collared shirt, a black bow tie that you tie yourself. Avoid the temptation to wear expressive patterns on your cummerbund and socks. I made the mistake once of attending a formal event wearing what I thought was a most stylish patterned cummerbund and tie and wing collar shirt. While being introduced to the former Secretary of State and several former other Washington big shots I realized I was the only dude in the room trying to push the style envelope. On the other hand, at formal events where you know there is more leeway, a smart and traditional look is a classic Black Watch patterned dinner jacket (or other tartan plaid). You’ll look like a leading man out of old Hollywood . But, please wear it with all your other other standard tux rig, the patterned jacket will be plenty to express your personal style and Holiday cheer. If you want to add a bit of pizzazz to your otherwise B&W outfit consider wearing a silk ivory scarf, or treat yourself to a set of interesting matching studs and cuff links. Brooks Brothers and Paul Stuart have a selection of tuxedos, including holiday plaids and accessories.
But even if your friends or social circle aren’t formal, there is no reason why you can’t create your own family formal traditions. I enjoyed seeing photos of a young couple on Styleforum who went to Tahoe for Christmas and New Years, cooked a Holiday dinner and wore formal attire in their cozy cabin surrounded by snow. They enjoyed the ritual and elegance of a formal celebration…just the two of them. How cool is that?
A Party With Friends:
There’s nothing wrong with being the best-dressed guy in the room, even though most of us hang out with a more casual crowd. You could wear a navy suit and white shirt sans tie (à la Tom Ford), or a blazer and flannels (maybe with a knotted neckerchief/scarf rather than a tie). For an artsy group, go with the perfect white shirt, scarf, dark trousers and killer shoes with a bad-ass black moto jacket. Here in the casual Bay Area, I mix something a bit formal with something casual. Tonight I’m going to a house party in Pacific Heights and will be wearing black double monks, jeans, a white shirt and a purple velvet jacket. I know everyone will be wearing something different and that’s OK. Hell, just foregoing a hoodie and T-shirt in San Francisco (and most cities these days) will make you one of the best-dressed men anyway.
So, have fun, don’t be shy about wearing something nice, avoid Christmas kitsch, and have happy and stylish Holiday season.