How to Win Friends and Look Super Fly at Your Holiday Office Party

Well, folks- it’s that time of year again- where holiday cheer and good tidings are served up with a nice big helping of awkward as you put on your schmooze-face and attempt to navigate the holiday party scene. I hope you’ve all dug out your ugly christmas sweaters (for that really originally themed party you were invited to) and have been massaging your livers in preparation for the inevitable onslaught of rum-spiked eggnog and shots of hard liquor you’ll be taking just to deal. 

Of all of these festive gatherings, perhaps the most difficult to maneuver is the office party. So many variables- so many opportunities to mess the hell up.  What should I wear? How much should I drink?   Should I take that novelty mistletoe hanging above my boss’ head literally?? 

Well, friends- I’m here to save you from yourselves (or at least from all of your ill-advised fashion choices) by giving you a list of do’s and dont’s for dressing for the  office party.  And for all you fellas in the house- while I could tell you what I like on guys, I have a feeling you’re probably not going to wear Skinny Jeans and a band t-shirt to an office party. So instead, I’ve enlisted my friend and co-worker, the ever-stylish Mike, who has recently started blogging over at Tremendously Tremendous,  to drop a few tips for the lads.

So lessssgo!:

For the Ladies: 

First and Foremost–> DO: Remember that it is office first, and party second. This is not a Vegas nightclub, ladies.. nor is it the Jersey Shore. DJ Pauly D will not be spinning any fresh beatz while Snooki and Deena grind in the background. Make sure that whatever outfit you ultimately choose is still work appropriate- and can be worn during the day with a cardigan or a blazer thrown on top. Also make sure it’s comfortable, the girls are firmly in place, and not too short or too tight. If you find yourself wondering “is my ass hanging out of this dress right now??” Then I’ve got two words for you: MEATBALL PROBLEMS!!!

 Secondly, DO: Amp up the accessories. A little bit of  bling can go a long way. Throw on a chunky necklace on top of a black sheath dress, or a statement pair of earrings. Hell, go a little crazy and spring for a big cocktail ring. .. but DONT: Overdo it. The last thing you want is to wear so much floss, you’re mistaken for T-Pain. Stick to one statement piece, or stagger your accessories- don’t just pile everything you own on at once like an Italian Nonna. And remember- if you are lucky enough to be sporting a grill: then that is allllll the accessory you need.

So, just to recap:

DO:                                                                                             DON’T:


Thirdly- DO: Experiment with colour/texture.  Try out a bold pair of tights, a printed shoe, a velvet blazer.. you can even get into the spirit by adding a little sparkle, or something red…  but DON’T go overboard with your interpretation of the word “festive“. Just because it’s a “holiday” party doesn’t mean you need to wear the shit out of a Swarovski crystal-embossed cocktail dress, or don some novelty Christmas Tree earrings.  Make your outfit “inspired” by the Holidays… not a walking, talking nativity scene. And please, please god- if it has any kind of picture on it- just do yourself a favour and burn that shit.

DO:                                                                                        DON’T:



And finally DO: Go a little more dramatic with your makeup. A smokey eye or a statement lip colour can take a corporate looking outfit into a new stratosphere… but DON’T: go for synthetic hair extensions,  fake eyelashes,  or a spray tan. Save those for that Real Housewives of Beverly Hills Season 3 wrap party you were invited to.  (And p.s. hook a sista up with a plus one, would ya??) 

DO:  The Smokey Eye                                          DON’T: The Courtney Stodden


 So there you have it, ladies- just a few tips to keep you looking superfly and mad profe$h at this year’s office party. And just remember: when in doubt, the answer is  yes…. yes you DO look like a two-bit hooker making the rounds at your friendly neighbourhood Appleby’s. Now put some clothes on, woman!!

Now… For the Gents:

A word from the Tremendously Tremendous Mike Mando

It takes advice from a fashion aficionado to look Tremendous at your Corporate Holiday Party. It just so happens that my ensembles have been complimented by numerous coffee server girls and bar maidens, so I feel confident in throwing some style tips your way for the Holiday Party season.

BreezyK Ed. Note: Say what you want about Scott, but boy does that man know how to rock a skinny suit

DO: Wear Slim Fit Everything (unless you’re more than a Deuce). Slim fitting suits and shirts hug and caress your body. The jacket follows your torso lines to give you a fit look. Slim cut pants accentuate your legs in a virile, “I-do-P90X” type way, and the tighter ankles draw attention to your shoes, which should be a focus point of your outfit. Keep this in mind, fellas: Shoes are usually the first thing a woman notices about a man. It’s science. Slim cut shirts show off your pecs and guns….and who doesn’t want that. Note- Slim fit DOES NOT mean airtight. Vacuum pack seals are for food and storage, not people.

 DON’T: Wear the Moore’s Box Cut Special (…Ever). Gentleman, think of the message you send when you put these monstrosities on. It says, “I don’t love myself enough to put effort into my wardrobe”. It’s not being metro to look good…and no one looks good when your suit jacket cuts you like a milk bag and your legs get lost in the over sized, swishy, billowy regular cut pants. And your shoes? What shoes? You can’t see them from beneath that bell-bottom. 

DO: Groom. I know this seems basic, but make sure your coiffe looks sharp. Get a trim and use product. If you’re going for a messy-but-pro look, use paste for a matte finish. If your hair is a little longer, and you want to look Don Draper-esque, use a gel (with the appropriate hold) for a sleek and slick (with a touch of shine for good measure).

DO NOT: Groom like an Idiot. Using the inappropriate hair product can be devastating. The messy spiky-pro look discussed above can quickly turn into the let-me-grab-my-glow-stick-and-hit-the-rave look. Don’t be that guy.

Another note from BreezyK on behalf of all the ladies out there: Absolutely DO NOT

 DO: Accessorize. Stick to basics for a classy look. Match belt to shoes, pocket square to shirt and/or tie. Wear a watch…and not your TIMEX. You’re going to a Holiday Party, not on a deep sea diving expedition. The band on the watch should match your suit. I opt for a black leather band and circular face for formal/semi-formal events. For a little added pizzazz, try ONE frill. A matching vest for a three-piece, a skinny tie as opposed to a normal one, or (dare I say) an ascot!! (NB: ascots should not be taken lightly. You better feel damn comfortable with yourself to pull off that look)

 DON’T: Accessorize like a Fool. Wedding bands, Stanley Cup and Super Bowl Rings are the only rings always acceptable for a man. Anything else is uncivilized (unless there is religious or cultural meaning, then scrap that comment). Necklaces must be worn beneath your shirt. You are not a mobster. Your watch should be proportionate to your body and outfit. Drawing attention to your watch is good sometimes, but not if it’s weighing down your arm. Then, you’re just a douchebag.

I pity the fool who wears this much bling to his corporate Christmas Party

 Follow these basic tips, and you will look Tremendously dashing for your Holiday Party.

Thanks Mike for the great tips!! Now Go and visit his blog for some more tremendousness 🙂

Question of the Day: Do YOU have any  tips for holiday office party fashion??    



15 thoughts on “How to Win Friends and Look Super Fly at Your Holiday Office Party

Add yours

  1. Good tips. Too bad I’m skipping mine. My best friend at work is some dyslexic kid that hasn’t been here in 4 years. He owns two shirts. God I miss that guy. If I had a reason to go (like the women here aren’t all 200 pounds and 50) I’d take these factors into consideration.


    1. I envy you and your dyslexic, two shirted friend… all of my friends have way more than two shirts. do you think that for every additional shirt you own, your interesting factor goes down one notch? Then maybe it becomes a viscious cycle, where you keep buying more shirts in an attempt to compensate for an uninteresting personality.. but it just makes you more and more lame. A “Shirt Complex” maybe. Think about it.


  2. Good tips, Bree. I’ll definitely be checking your lists before going to one of my school parties. The other one, however, is the ugly sweater variety, so in that case, do all your dont’s turn into do’s???except the whore of Babylon tips? I’m guessing that one is consistent across the board?


    I’ll require a consultation, I’m sure!


    1. I would like to see you try to dress like the whore of babylon while wearing your christmas sweater. It may be a “Don’t”, but it would sure as hell be an accomplishment.


  3. Being told I cannot wear much bling makes me want to challenge the notion and wear so much bling it blinds everyone in my path from all the sparkling. There’s making an impression and then there’s being lit up like the electric cowboy. Yeehaw.


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