How to Dress for the Holidays

Dressing for the holidays is always a bit of a challenge – where do you draw the line between formal style and holiday cheer? Should you always wear a Santa Hat or Rudolph Nose with your tailored khakis?

Not to worry – we’ll break down how men can dress for the holidays in a variety of situations.

Don’t Overdress

For starters, remember not to overdress for the event you’re attending. Thanksgiving dinner might be an important tradition in your family, but that doesn’t necessarily mean you need to show up in a three-piece suit. Holiday parties may mean that it’s time to bring out a tie, but there are still ways to construct a fashionable, but casual outfit.

Start with standard men’s choices: dark sweaters, dark slacks, everything fitted to perfection. But you do have a little more flexibility during the holiday season to get fun. After all, it’s the holidays! Don’t keep things boring or overly formal by showing up in a suit to every event. Get a little creative!

Picking the Right Sweater

It all starts with shirts and sweaters. If you're attending a cocktail party or a more fun-oriented holiday event, don't be afraid to break out an ugly sweater with a graphic or knitted design. Sweaters or long-sleeved shirts in wool are ideal in practically every holiday event. Choose your colors from dark green to red to blue or even gray. Generally, the closer you are to Christmas, the more color is needed in your outfit.

Tailored Trousers – Stylish or Silly

When it comes to leg wear, you have a lot of options depending on the event you’re going to. Is it a work event where you’re supposed to be serious or more formal? Go with stylish yet understated trousers. Alternatively, you can lean into the above-mentioned ugly sweater aesthetic and choose more colorful, bombastic pants to celebrate the holiday season.

One great example of comfortable yet stylish pants that'll go with any cocktail party or holiday outfit is Berle’s Narrow Wale Cord Flat Front Pants. Designed with a super soft poly corduroy pattern and a relaxed fit, these trousers are ideal for darker wardrobes or more serious after-office parties.

If you want to be a little more festive, Berle’s Fancies Collection has everything you need to spice up your outfit and bring some holiday color to your ensemble. Take these Royal Steward Wool Plaid Pants. The red and green plaid can be a perfect pairing with a warm holiday sweater and Santa hat.

Recall our advice about dressing for the occasion, however. If you need to dress yourself up a bit for an office event or more formal party, Charleston Dress Khakis could be great for pairing with a dress shirt and coat. Ultimately, the flexibility of men’s trousers means that there’s always leg wear suitable for your holiday party or appearance.

Get Fun with Accessories

Your accessories often allow you to get in the holiday spirit and improve your outfit even if you don’t deviate too far from cold-weather male fashion. We’re talking things like bracelets, hats, or decorative belts/belt buckles. If you’re wearing a suit, consider getting a tie with snowmen or other wintery icons to lighten the mood while still adhering to formal outfit rules. Or consider a Christmas-themed watch, one with Santa on the front instead of a Rolex logo. The sky’s the limit when it comes to accessories!

Tuxes and Suits – When Are They Needed?

Lots of people get married near the holidays. But you might also have to attend more formal galas or other events. In those cases and more, a tuxedo or suit made of wool or a similarly thick material is just the ticket. Fortunately, tuxes and suits should keep you plenty warm and essentially decide all of your clothing choices for you. Odds are you already have a tuxedo or suit to wear; break it out and make sure it is still tailored for your body size and you’re good to go.

Don’t Forget Footwear

Last but not least, don’t forget to consider your footwear. Your shoe wardrobe may need a little updating for an upcoming cocktail party or holiday bash. Patent leather loafers are perfect for a relaxed and dressy-casual event, especially since they can be worn with a suit, denim, and everything in between. Or consider versatile boots that are great for stomping through wet streets to get to your destination.

Whatever you do, don’t wear sneakers to a holiday event!

As you can see, there are lots of ways to dress stylishly as a man for the holidays. So break out your ugly sweater, make sure your trousers are tailored, and have fun!