Style Guides

What to Wear During the Holidays

‘Tis the season of the holiday party! Are you looking forward to the soirees on your calendar or dreading them? Are you ever confused by the “suggested attire” section of an invitation? While “Ugly Sweater Party” is quite clear, dressing like a gentleman isn’t always easy to master.  

Treat Every Event as an Opportunity to Shine

Even if you don’t normally wear a suit to the office, the holidays can give you a chance to make a good impression. It’s not just the season of peace and fellowship; it’s the season of networking. Attitude matters. And a party is rarely “just” a party. At these events, you unwittingly have the power to make or break your reputation. That’s why we encourage you to make a confident entrance and mingle with a purpose.

Our best advice to you: dress appropriately for the occasion, and don’t fall back on holiday sweaters or khakis and polos that do you no favors. Just as you wouldn’t have too many drinks in front of the boss, you wouldn’t mess up your reputation by doing something sloppy with your wardrobe.

For a Cocktail Party, Strive for a Mix of Crisply Formal and Stylishly Casual

For a cocktail party – or, in fact, any special event like a wedding or awards dinner – you’ll want to go semi-formal. You don’t need to dress in a full business suit, but you’ll still want to err on the side of business-like. You do have freedom to add some personal touches; accents like a nice tie or pocket square are certainly appropriate. But please, no novelty ties, and leave the Christmas sweaters at home. Think semi-formal, yet elegant, with a little room for personal expression.

Here’s what else we recommend:

  • Dress in dark colors. They’re flattering on just about anyone. You can go with earth tones, charcoal gray, navy, or black. Avoid loud colors for an event like this.
  • Wear a tailored pant or shirt. Making sure your outfit is tailored is key when you want to add class to your look. People will wonder how on earth you look so sleek and put-together.
  • Add a layer. But do it without bulking up in a sweater. Choose a blazer or a simple vest instead.
  • Wear polished dress shoes. Instead of loafers, go with formal shoes, and make sure they’re shined!

Let Your Personality and the Occasion Guide You at a Casual Holiday Party

When it comes to holiday parties, there are all sorts. Some are ultra casual, some are rowdy and festive, others are intimate and warm. The way you dress will reflect both your personal style and the type of event you’re attending.

For those of you who secretly love to rock a festive Christmas sweater, this is your opportunity to shine. At a holiday party, it’s okay to choose a pair of fresh kicks or loafers over a business shoe. The trick for holiday parties is to be easy-going, but not sloppy.

Here’s what we recommend you try:

  • Be dashing in denim. It’s okay to wear jeans to a holiday party, but keep them dark. Leave your acid-washed, ripped, or skinny jeans at home. If you don’t yet own a pair of non-distressed dark denim, it’s time to go shopping.
  • Leave the business overcoat behind. At holiday events, it’s more appropriate to wear a more casual jacket, fleece, or coat.
  • Wear seasonal colors. They’re made for events like this. We recommend experimenting with darker or lighter shades of red. Try layering a soft, forest green sweater with a pair of chinos and a cool pair of Chelsea boots.
  • Add festive accents. Consider pairing a sweater or cardigan with a festive accent – a patterned sock or holiday tie, for example. Remember: you can be festive without being obnoxious.

Keep it Professional at Your Annual Office Party

Usually, we encourage our clients to take fashion risks, but for this one, we’re going to break our own advice. More than any other event, it’s important to keep your look rather professional at your annual office party.

We realize that our advice depends, in part, on your workplace. For some startups, you can get away with wearing a pair of jeans, a T-shirt and hoodie, and a pair of Chuck Taylors. For most of us, however, a dress pant and button-up shirt is more appropriate. Remember, your bosses will be there and, more importantly, so will their bosses.

Here’s what we advise for your next business get-together:

  • A pressed and well-fitted shirt is a must. Don’t throw on that wrinkly Oxford shirt. Wear your best combination of dress shirt and pants and pay attention to your gig line.
  • Experiment with patterns and textures. It’s cold outside, and it’s a festive event, so you can wear a thicker blazer or go with a unique pattern like a houndstooth, argyle, or tartan.
  • A blazer with no tie is a great look to imitate. You’ll want to avoid looking stuffy in a business suit, but still make a nice impression.
  • No sneakers. Wear some polished shoes or boots instead.

Black Tie Party? Here’s Your Chance to Show Off   

There are going to be a few black-tie shindigs on offer every year. Want to make an impression and truly shine? This is your chance to sport a tux or dazzle with luxe accessories.

Don’t own a tux? Don’t worry. You can put together a DIY version. Pair a tailored black suit with a crisp white shirt and a black bowtie – it’s completely acceptable. If you want to try a slightly edgier look, you can go with a midnight blue suit. You can also add a velvet accent or a richly colored bow tie and pocket square. However, you don’t want to go too far away from the standard black-and-white. Your goal is to stand out and look sharp, without being “that guy.”

We recommend these tips:

  • Stick with the classics. Wear a standard tux, a three-piece suit, or a dark dinner suit with a satin or velvet accent.
  • Add some luxury. This is your chance to wear that heirloom watch or try on those cufflinks you never get a chance to wear.
  • Go for James Bond, not Rick James. We like the funky beats of Rick James as much as the next guy, but we don’t recommend pimping out like he does. Think sleek, not flashy.

Let BillyGrey Help You Look Your Best Well into 2019

If you’re not confident about the way you look, and you’d like to be, give BillyGrey a call. We can help by selecting pieces that accentuate your natural coloring and personality traits. At BillyGrey, our focus is on you.