Man in holiday sweater and Christmas hat

What to Wear to a Holiday Party 11 Menswear Bloggers Show Us Their Favorite Festive Attire

We can hardly believe that Christmas and New Year’s are (literally) around the corner. In the midst of buying last-minute gifts, going out with friends, and wrapping up work deadlines for the year, time goes by ridiculously quick. However, despite all the craziness, there’s certainly one thing to look forward to when the holiday season hits: holiday parties. They come in all shapes and sizes, from small office gatherings to ugly sweater white elephant exchanges, to all-out jam-packed ragers, and every other variation in between. Holiday parties are the cream of the crop when it comes to getting dressed and going out. For all of the festivities you’ve got lined up over the next few weeks, you’re gonna need to know how to dress up and look your best. We’ve asked top menswear bloggers from the Style Guru Society to weigh in on holiday party looks, and show us how they will be dressing up for the office party, the casual get-together, the ugly sweater party, and the formal gathering. Read on for their best looks and style advice to get you through the season in style.

Table of Contents

The Office Party

Rick, The Wingtip

Rick Reyes - Office Party Outfit

Phoenix Red Tie

The Phoenix tie features a checkered pattern that is playful yet refined. Choose this red accessory to add a splash of personality to your dapper ensemble.

“What is the first thing that comes to mind when you hear the words “office party?” To many, that entails men in boxy suits and women in boring pant- or skirt-suits gathering in cubicles. Does it really mean that, though? We now live in a very dynamic and progressive era. Granted, we live in California where people feel more comfortable wearing beanies and sweatpants. Nothing wrong with that, but the West Coast, the idea of dressing up seems to have taken the passenger seat while the East Coast takes all the credit. For that reason, I want to let you guys know that dressing up for the infamous “office party” does not have to be a burden. Rather, it can be a rather joyful experience! It is your time to shine and stand out amongst a sea of boring office outfits.

As you can see, I decided to ditch the full-blown suit and add a more modern and young look to my outfit. You definitely want to add some sense of formality; after all, it is a business party… right? So, you can accomplish that by wearing a solid white shirt and well-tailored suit pants. Then, give it a modern twist by adding textures! A wool blazer and a wool tie (powered by make your outfit stand out amongst the masses. Yeah, yeah, it may not be as cold here as it is on the East Coast. So what? Are you going to let your outerwear just gather dust in your closet? Use your holiday parties as an opportunity to bring out the coat and layer it over your blazer. Finally, bring your most polished briefcase, and you’ll be prepared to both ace your morning business presentation and wow your coworkers at the lunchtime party, with ease.

Ultimately, the point is that you feel comfortable and confident in what you are wearing. Throw in the piece you like the most and wear it with pride. Remember, although it might be an office setting, we are a new generation when it comes to business attire. It is up to us to change the dynamic and culture of the 9-5 world. Merry Xmas!”

Matt, RunninEverlong

Matt Hartman - Office Party

Ugly Christmas Sweater Navy Blue Tie

Pull a fast one on everyone and show up to your next ugly sweater party with not a sweater, but a tie! Our navy blue Ugly Christmas Sweater Tie has all the fixings of the signature sweater without you actually having to wear one.

“When I attend a holiday party I want to make sure I ‘stand out’ from the crowd.  An easy way to do this is by your outfit, of course.  I focus on wearing something that is a touch of class with some personality, but nothing tacky.  There’s a fine line there when it comes to holiday parties, and that has been very carefully considered.  My career has been in large and medium-size organizations, so holiday parties are one of the few times I actually get to meet new people.  I want to make sure I make a good impression.  This year I’m wearing a sweater with a cool tie so I can be comfortable but fun at the same time.”

Carl, New England Style Consulting

carl-murawski - office party

“I like to work with colors which draw from the holiday color palette without directly referencing any imagery. Reds, greens, deep shades of burgundy, etc. all work well together and bring to mind the warm feel of the season. It’s also the perfect time to bring out heavier textures, which I did with the pocket square and tie.”

The Casual Get-Together

Ryan, Brick and Vine

Ryan Rosenkilde - Casual Get Together

“For a casual holiday gathering, I’d go with one of my solid outfit go-to combos: denim on denim. For me, it’s a classic ensemble and it feels very comfortable, which is important if you’re going for a casual look. Since it is the holidays, after all, ditch the regular denim jacket and go with a sherpa trucker jacket instead. It’ll give your look a more festive, wintery feel.”

Jake, Oxford & Henley

Jake Palmer - Casual Get Together
Jake Palmer - Casual Get Together

Red & Pink 4 Pack Waxed Multicolor Shoelaces

Liven up any shoe with this 4 pack of 100% cotton colored shoelaces. This pack includes a pair each of Ginger Red, Carnation Pink, Burgundy Wine, and Flame Red shoelaces. Wax coating keeps the laces tied tight throughout your day. One size fits most; measures 28 inches.

“With the holiday season upon us, there are lots of opportunities to get together with friends and family. Most of these for me are going to be casual events. What I love about this time of year and especially the weather is that it allows for layering. I will usually go with some kind of collared shirt and sweater combination. If it’s cold, I have the sweater to cover me up, and if it gets a little warm I can always take it off. While I went more plain with gray and white tops, I added pops of color with green pants and red laces on my shoes. Have a great holiday everyone!”

The Ugly Sweater Party

Devon, Dminnisct

Devon Minnis - Ugly Sweater Party

“There are a ton of different ways to style an ugly Christmas sweater, and my look definitely is done with the idea of being casual and comfortable in mind. This look is perfect for the weekend, family gatherings, or even parties with friends. I am wearing an ugly Christmas sweater vest layered over a nice white turtleneck, which I then paired with chinos. This is a great casual look and will keep you comfortable all night long no matter what your festivities have in store. Feel free to style with a minimalistic watch and some bracelets!”

Baker, Ape is Dapper

Baker - Ugly Sweater Party
baker - ugly sweater party

“You get the invite every year. Some friend is throwing a party, and the dress code is that sweater you only wear once a year. And, it’s ugly. I’m not the biggest fan. So, when Ape gets dressed for ugly sweater parties, this outfit… well, the tie, is the solution. It’s just enough of the right aesthetic so that your friends won’t complain about you not wearing an ugly sweater, even though you aren’t. As for the outfit, I basically worked around the tie. The green oxford complements the Christmas tree design in the tie. The sweater is pretty damn Christmassy, too! You simply can’t go wrong with a thick shawl neck cardigan when it’s cold out. It’s a far cry from ugly, but that’s the point! I went with these chinos because khaki works with everything– it brings balance to the outfit. I couldn’t really explain the shoes and socks, though. I just figured they’d look good. Happy holidays, folks! Enjoy an eggnog or something for us.”

Jason, Oxford & Henley

Jason Trinsey - Ugly Sweater Post

“When attending an ugly sweater party, be sure to wear a sweater that means something to you, so if someone asks, you can explain it. In my case, I love “A Christmas Story” so this sweater was a major award of a purchase. For the rest of the outfit, don’t be afraid to go all out–greens and reds. Oh, and don’t forget the Santa or elf hat to complete the look. Sometimes I even like to wear a shirt and tie underneath to start the party. You can always undo the tie and collar as the party progresses.

It’s also important to remember that it is courteous to bring something like food or alcohol (or both) as a sign of thanks. Make sure to greet everyone appropriately, be safe, make memories, and don’t leave without saying goodbye and thank you!
Happy holidays to all!”


Steve, The Social Cut


“I’ve never quite understood the concept of the “Ugly Christmas Sweater” party. It must’ve been an excuse from some style-challenged guy that once showed up to a Christmas party wearing a terrible sweater, and played it off very well. As modern-day gentlemen, I say we do away with the ugly Christmas sweater this year and go with something more stylish that still keeps the holiday spirit! This holiday season, opt for a shawl collar cardigan with a festive pattern (I said festive–don’t get carried away) and pair it with a solid-colored turtleneck to earn those extra style points. A hat and sunglasses are optional. You’ll look casual and will definitely get heads turned your way.”

The Formal Gathering

John, Bull And Blossom John

john-tjaarda - formal gathering

“I think it’s important to not overdo a “classy event,” which says a lot coming from me, especially when so many people might consider my outfit to be overdoing it. I’ll start with the jacket.  I found the jacket itself at a consignment shop for $10 and had my tailor add the bias tape to the edges for another $30.  This jacket goes a long way in expressing my personal style so I didn’t need much else to do any of the talking for me.  I picked a festive, silk bow tie that didn’t clash with the mood of the jacket.  I went basic with my shirt and pants because I didn’t need them to do any work other than to keep the look grounded and simple.  I finished with a black and white floral (so hot right now) pocket square.   Overall, this isn’t something I wouldn’t wear day-to-day, which to me, is the entire point of attending classy, sophisticated events. You want to dress up, sure, but you also want to stay true to who you are and choose pieces that help you express your personal style.”

Mitch, Meeeotch

Mitch - Formal Gathering

Cocoa Brown Tie

The ultra satin finish of this stunningly lustrous solid cocoa brown necktie brings amazing depth, dimension, and a vibrant sheen to its 100% silk construction.

“I will be wearing a Robert Talbott plaid tuxedo pair with a crisp white shirt and black tie for this weekend’s formal holiday party. I chose this look because I wanted to be the best-dressed person at the party. 🙂 I know that most people will either wear a black suit or a traditional black tuxedo, and I wanted to stand out in a good way. I know my audience and I also know the tone of the party. I feel like this plaid tuxedo will not only turn heads but be memorable. When dressing for a formal gathering, know your audience, stay true to your style, and make sure that you love what you’re wearing. There’s nothing worse than wearing something you’re not completely committed to.”

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