Don’t Arrive Under or Overdressed! 6 Holiday Fashion Tips

If you have a holiday party or two on your calendar, you’re probably trying to figure out what to wear. If you’re going from the office to your company’s party, then you can probably wear whatever you wore to the office. But things are more difficult to figure out for just about every other kind of holiday party. What should you wear to the party at your friend’s downtown loft, the weekend get-together your coworkers have planned for their favorite bar, the dinner party your significant other’s best friend is hosting, or the cocktail party you were invited to by a friend of a friend?

Luckily, getting dressed for each of these parties isn’t as complex as it seems. With a few logical moves, you can make sure that you won’t show up at a gathering and feel either underdressed or overdressed all night. Here are our tips on feeling right at home at each holiday party on your calendar, whether that party’s right around the block with all your best friends or in an unfamiliar part of the city with lots of people you haven’t met before.

1. Assess the context

Christmas party, holiday, toast

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If you’re not sure what to wear to a party, there are a few ways you can try to figure out what’s appropriate. Try to determine where everyone will be coming from. If they’re all going from the office, they’ll likely be dressed more formally than if they’re assembling for a casual weekend get-together. Take a look at the invitation; if it says anything about the dress code, then you have a major clue to work with. And if it’s a theme party, things get even easier. An ugly Christmas sweater party, for instance? No one’s going to care whether you wear jeans or chinos with that dizzying reindeer knit.

2. Prepare for a change of plans

man straightening tie

Source: iStock

If you’re really unsure what to wear, and don’t have a friend in the know to clue you in, then you can carefully plan your outfit to allow for a little bit of latitude. It’s always a good idea to wear a blazer, a button-front shirt, and a tie. You can tuck the tie into your pocket if it seems like overkill. Or, if your friends are already knocking back shots when you arrive in a full suit and topcoat, don’t be afraid to take off the coat and suit jacket. You can also make an ensemble look less formal by rolling up the sleeves of your shirt. The point is that if you’re unsure of what to wear, you should err on the side of formal and plan to make modifications if you need to go a little more casual.

3. Layer judiciously

A smart move if you’re still not sure how to dress is to fall back on a perennially useful winter strategy: smart layering. If you really aren’t sure how guys are going to dress at a party being held by someone you don’t know very well, a great way to go is to layer a sweater under your blazer. It’ll look formal in a formal situation, but looks more casual than a blazer directly over a dress shirt if the party ends up being more casual than you expect.

4. Avoid wearing black

Another easy rule if you want some latitude in how casual or formal your outfit will look is to avoid wearing black. Especially if you’re wearing a suit, a blazer, or even a topcoat, you can avoid feeling overdressed or underdressed by choosing the color judiciously. Black often looks quite formal, while an alternative like navy can read either casual or formal. For instance, a navy suit can look festive with a red tie in a way that a black suit or blazer wouldn’t achieve.

5. Go for whimsical details

holiday party, christmas, bar, drinks, alcohol

Source: iStock

If you’ve decided to wear a blazer or a suit but are worried about feeling overdressed, you can hedge your bets by adding whimsical details to your ensemble. Opt for a colorful or patterned tie over a dark one, or break out the bow tie instead of wearing a straight one. Have fun with your pocket square or your cufflinks, or add a holiday-friendly scarf or hat if you’re in a cold area. Bright or fun details won’t detract from a formal outfit in a dressy setting, and will make that same outfit look more appropriate in a casual setting.

6. Adjust your attitude

While you can avoid being overdressed or underdressed in many situations, sometimes even the most meticulous planning won’t prevent you from walking into a party and still being dressed differently from everyone else in attendance. The best way to handle that is to let your attitude reflect the vibe of the party, even if your clothes don’t. If you walk into a Saturday night party in a tuxedo but don’t act stuffy or buttoned-up, then it won’t matter if everyone else is in more casual blazer and trouser combinations or even in jeans. And realize that it’s okay to stay true to your own style. You can wear a bowtie and blazer to the most casual of parties if the combination is your signature, and no one will think twice about whether you’re overdressed for the party.

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