3 Great Holiday Outfits: Be The Best Dressed Gent in the Room

Holiday parties are good for more than just gathering precious dirt to use on your coworkers for the upcoming year.

You know, like when that quiet guy who normally stares at his phone during meetings has a few too many drinks and takes his shirt off.

We wait all year for that sort of rare behavior.

Obviously, that’s not going to be you this year (hopefully it wasn’t last year, or the year before, either).

This year, your holiday outfit is gonna be on-point! We’ll help you be the best-dressed guy in the room.

Wanna know how I know?

Because you’re going to read this article… that’s how I know!

I’m going to break down three different outfits you can wear to any holiday party.

• Got a work party and need to look sharp? Take a look at outfit #1.
• Need to make a good impression with your new in-laws but don’t want to over-do it? Outfit #2 is a classic and won’t let you down.
• Getting together with friends and want to spruce things up a bit? Look no further than outfit #3.

No matter what joy or trauma you’re up against this holiday season (we can’t get shirtless Joe out of our heads!) make sure your outfit is one of the highlights.

What’s Different About Holiday Outfits?

You don’t have to go over the top and wear a pointy red hat. No, that’s not what this is about.
When you’re rollin’ to a holiday party, do you really want to wear the same outfit you wore to work earlier that day?

Of course not! ‘Tis the season and all that jazz.

• Feel free to get into the spirit with rich burgundy and forest-green tones.
• Layer on your thicker fabrics like wool and flannel.
• Bust out those suede shoes.

The holidays are the best time to bring out all those richly textured items in your closet and let them shine.

Can’t I just wear that gimmicky suit I bought for $30 off Amazon?

I once watched a man walk into a holiday party with such a suit. He bent down to pet the dog and completely blew the seat and crotch out of his pants.

After everyone had a good laugh at his expense, he started saying his ‘hellos.’

When he gave the host a hug, his suit jacket busted open at the back and, as far as I know, he’s never lived it down.

You can wear that gimmicky $30 suit. I just hope you have a thick skin. A very thick skin.
And some nice underwear.

Ok, no gimmicky suit, so where do I go?

We used Peter Manning’s catalog to put these three outfits together. We’ve been huge fans of Peter Manning for a while now and we’re proud to partner with them again for this article.

Peter Manning specializes in making clothes for not-so-tall guys who typically need a 30” inseam or shorter. If you find yourself regularly going to a tailor (or just skipping the tailor and living with shirts and pants that are too long) you need to know about Peter Manning.

Good news, fellas. The first 100 Effortless Gent readers who head over to Peter Manning can get 20% off by using the code EG20 at checkout.

Insane.

Not only do they make pants with inseams sizes 25”- 30”, they design their whole collection with the shorter gent in mind. That means v-necks don’t cut too low, shirt sleeves fall where they’re supposed to, and sweaters aren’t comically long.

A well-curated wardrobe from Peter Manning will ensure you’re the best-dressed gent in the room.

Taller than 5’10” and PMNYC doesn’t work for you?

We chose these items because they’re fairly common, so don’t despair if you’re taller than 5’10”. You can easily pick up similar versions of these items elsewhere.

Let’s get into the outfits, shall we?

#1: What to Wear to a Holiday Office Party

Everyone’s office is a bit different… some keep a tight ship and basically require a suit and tie to the holiday party.

Others hand out those silly jingly reindeer hats that make everyone look ridiculous.
Let’s just go ahead and assume you don’t want to look ridiculous.

Grey suit (jacket and pants), (option 1) black watch shirt / navy tie, (option 2) red stripe shirt / green tie, black cap toes

Even if you’re wearing a suit, holiday parties are more relaxed affairs (hopefully). A grey suit is a perfect choice. You’re dressed up, but you’re not going formal with a black or deep-navy suit.

For parties, I love putting on something patterned underneath my jacket. If you’re going for a subtle look, pair your suit with this Black Watch Plaid Everyday shirt from PMNYC. The navy and hunter green are festive without loudly announcing themselves.

Wear it with a solid, textured navy tie and black shoes to complete the look.

Some of you won’t settle for rich, subdued tones.

Some of you just need to pump the Christmas bass… that’s cool.

For you, put a solid hunter green tie on this red university stripe shirt. You don’t have to be obnoxious to show your holiday spirit after all!

With both options, we love the Allen Edmonds cap-toe oxford. It’s a formal shoe, but the brogue detail along the cap adds a little ornamentation to celebrate this special time of year (and also dials down the formality).

#2: What to Wear to Family Dinner

If it helps, you can think of a holiday party as the “final boss battle” on your quest to mastering texture layering.

This outfit has it all… denim, corduroy, wool, suede. It’s like an all-star cameo-filled outfit featuring all the winter favorites.

Navy cords, denim shirt, burgundy sweater (PMNYC option / Uniqlo, pictured), herringbone sport coat (PMNYC option / J.Crew, pictured), camel top coat, tan suede Chelsea boots

If your office party will be a little less formal, you can go with this combo, but this is a great choice for heading over to the in-laws for dinner. You know, those moments when you need to punch it up a bit but you don’t want to look like you’re trying too hard.

Start with an unstructured and minimally-lined wool blazer. If you’re going for a smart casual style, it’s important that you choose an unstructured blazer. Jackets that have lots of structure can be good for the office or any formal occasion, but you don’t want to look like you’re walking into a job interview when sitting across from your father-in-law (even if you feel that way).

From there, we put on a denim shirt…again, going with a casual shirt to keep things relaxed.

Layer a rich burgundy Merino wool sweater on top for the classic blue and red holiday pairing.

You can go with dark denim (just make sure they fit well), cotton chinos, but if you want to take things to the next level, hit ‘em with the corduroy pants.

The Kittredge Cord from Peter Manning is textured enough to look rich, but they don’t become distracting. Corduroy got a bad rap after some brands took it too far. Luckily, Peter Manning is restoring the good name.

Go full stunner with a pair of suede Chelsea boots on the bottom. The light color here really pops. Voila, your texture masterclass is complete!

#3: What to Wear When Getting Together with Friends

Ah, yes. You’ve noticed the tree doesn’t have ornaments. It has liquor singles.

You must be at a friend’s holiday party.

Good thing you didn’t wear your suit.

Navy chinos, gingham shirt, quilted vest, leather jacket, cream cashmere scarf, black sneakers

When going to a casual gathering with friends or coworkers (not the office party), you still want to put in some effort.

Now’s the time to show off the best of the best in your casual wardrobe.

For us, that’s a cashmere cream scarf and lambskin leather jacket from Peter Manning. Seriously luxurious.

Break up the solid colors with a nice grey and burgundy patterned oxford, and do a classic pairing with chinos. These bottom layers are staples, so hopefully, you have some in your wardrobe already. If not, get on it!

Since its winter and I hate the idea of freezing to death, I like to add a mid-layer. My go-to is the Flatiron Vest. This thing gets so much use in fall, winter, and into spring. I don’t know what I’d do without it.

Of course, on top of the vest, you have your show-stoppers…the cashmere scarf and leather jacket.

Finish the look with some black Greats hightop Royals. The black leather pairs perfectly with the lambskin leather jacket, but keeps things casual and relaxed.

Ready for the Holidays?

Well, we can’t help you with the family and office politics.

But we can help you look great as you scramble for an excuse to head outside and take a breather.

If you head over to Peter Manning and use the code EG20, you can get 20% off your entire purchase. But the offer’s only good for the first 100 readers who head over, so if you want to bump up your holiday style, jump on this deal while you have the chance.

The holidays are a special time. You could wear the same stuff you’ve been wearing all year… but where’s the fun in that?!

Step it up this holiday season, and if you’re lucky, grandma will slip you an extra twenty from her purse. Rub that in your cousins’ faces.

Want a few more holiday outfit suggestions?