During the holiday season, typically from Thanksgiving to New Year’s, you will probably participate in numerous parties, dinners, gatherings, and other festive situations that require a specific set of attire. You should show respect for the host and other attendees by dressing festively for the event while still maintaining your gentlemanly style. We’ll review the holiday attire for men for the most common festivities.
The basic holiday events below will require a special outfit or at least that you dress up a bit more than usual.
- Thanksgiving dinner
- Holiday parties
- Holiday dinner
- New Year’s Eve
Versatile pieces
Before we dig into the different scenarios, we should note that it’s better if you can purchase pieces that you can wear for at least a couple of these situations or outside of the holiday season. And anything overly flashy, like a bright green blazer for instance, can only be worn once (maybe twice) during a season. A blackwatch plaid sport coat is a better alternative. While still festive, you can wear it multiple times during the holidays and beyond because it’s not so loud.
The holiday attire for men below will offer more versatility and classic gentlemanly style during the season:
- Blackwatch or green plaid shirt or sport coat
- Red flannel patterns
- Dark green or burgundy sweaters instead of brighter green and red sweaters
- Fair Isle sweaters/cardigans instead of “ugly” sweaters
- Navy blue, burgundy, or dark green corduroy/flannel pants
- Velvet dinner jacket (if you do fancy stuff)
The gentleman above all look sharp and festive without veering into clownish looking territory. One thing to note is how they complement these bolder pieces with the simplicity of the rest of their outfits.
If you do want to wear something flashier, you can always experiment with accessories. A bright red or green scarf or pocket square, a holiday print scarf, or some holiday inspired socks are easy ways to show your festiveness without looking too over the top.
If you love a specific holiday and do want to splurge, then you should. Get that crazy Santa sweater and wear it proudly. Just know that its use is extremely limited, and sometimes these pieces can come off more gimmicky than gentlemanly.
Thanksgiving
The level of dressiness completely depends on the family who is hosting the dinner. If your significant other’s family keeps it pretty casual, then some nice dark denim and a lambswool or merino (or Shetland wool) sweater over a button down will cover most situations. Even if they lean super casual, don’t show up in worn-out jeans and a hoodie.
Obviously ask your significant other about what the men typically wear, and try to stay in that general zone. If your family is hosting, again you should set a minimum standard mentioned above even if everyone else is super casual.
For slightly dressier situations, you can swap out the dark denim for chinos or flannel pants. The sweater over a button down will usually suffice, but you can add a brown sport coat on top (or replace the sweater with one) if you so desire.
Some families really like to dress up for Thanksgiving. In this case, I would definitely go with a brown or grey sport coat, some flannel or nicer chinos, and a subtle patterned or plain white/light blue button-down. A chunky shawl-collar cardigan is a wonderful option too in place of a sport coat.
Holiday party
For a work holiday party, you should lean a little more conservative. One festive piece for your outfit should suffice. A dark green or burgundy sweater and some navy blue cords will work for most casual work situations. A blackwatch plaid sport coat over a white button down or a blackwatch plaid shirt with some grey flannel pants would be fine too if your company is a little dressier.
If there is a clear theme, then it’s at your discretion to choose how much you want to fit in. For work parties, it’s best not to be the most outlandishly dressed person. You do want to exude a gentlemanly attitude while showing the appropriate level of festiveness.
Also, watch your booze intake. No one should threaten their career prospects because they got too drunk at a holiday party and did something inappropriate.
For friend-hosted holiday parties, let loose a bit. If you’re feeling like one subdued festive piece for your outfit is appropriate, then follow the work party guidelines above. Otherwise feel free to bring out your outlandish holiday sweaters/sport coats, Santa hats, snowflake scarves, etc…
If you attend fancy holiday parties, like a charity benefit or a formal holiday ball, this is a great opportunity to sport a holiday-inspired dinner jacket. A burgundy or dark green velvet dinner jacket, or a blackwatch plaid dinner jacket, can look great if you have the sauce to pull it off. Otherwise, the typical black tie attire will more than suffice, and you can add some festive-ness with a red, green, blackwatch or red plaid bowtie.
Holiday dinner
This event may coincide with a religious service, in which case you’ll want to dress appropriately for the situation. Even for a casual religious setting, you should sport festive yet conservative attire. Something similar to your subdued office holiday party outfit should suffice (dark green/burgundy sweater or blackwatch plaid sport coat over a white button down, navy/brown cords or dark grey flannel slacks, and a pea coat or overcoat if it’s cold). You can always add some color with a holiday-themed scarf.
If you or your significant other’s family normally dresses up for your holiday dinner, you can take your look in a couple different directions. Again, the blackwatch plaid sport coat can work great here (noticing a theme?). A medium or dark grey suit with a festive tie can check all the boxes too. A charcoal flannel sport coat over a white OCBD and either a red or green sweater and grey or brown flannel slacks, or ditch the sweater and sport some dark green/burgundy cords. Either way you’ll look sharp.
If you’re skipping the religious service, your bare minimum level of dressiness should be some nice dark wash jeans and a festive sweater. Or you could switch the sweater out for a holiday flannel patterned shirt and a down vest. This basic holiday attire for men can provide a fallback outfit if you’re unsure.
New Year’s Eve
You can finally ditch the holiday colors! If you do choose to go out on New Year’s Eve, you can dress in more typical attire based on the type of event you attend.
A black-tie event gives you an easy decision. You can maybe squeeze in one last wear of a velvet dinner jacket if you so choose. The blackwatch plaid might be too played out by this time in the season, but a burgundy or dark green velvet dinner jacket could work. Personally, I think standard black tie is your best bet, but let your personal style guide you for this event.
For something less formal (maybe a nice dinner out and some quiet drinks), some cold weather semi-formal attire will work best. A grey or brown tweed sport coat, a white or light blue OCBD, some grey or navy flannel pants, and maybe a camel or navy merino v-neck sweater will get the job done quite nicely.
Get 2-3 festive pieces
Holiday attire for men can present problems if you don’t prepare properly. You only need a couple of festive pieces to handle all of your holiday needs. The rest can be filled in with neutral cold weather attire to complement and highlight these individual pieces.
And when in doubt, you can always throw on a festive scarf, cardigan, and/or socks to make things work.
