Outfits: Holiday Parties

It can be hard to pick out an appropriate outfit for occasions like holiday parties.  Different types of parties call for different levels of dressiness.  And as a butch, it can be especially hard to decide how dressed up to get.  Worse, many of us fall into the trap of dressing like an old dude with baggy khakis and an ugly sweater and excusing ourselves by saying we are being “funny” or “ironic”.  This year you don’t have to dread every party because it’s awkward and uncomfortable to dress for.  Here we lay out good-looking outfits for three typical holiday party scenarios.

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Casual Party with Friends

An evening party with friends is a great chance to step up your casual dressing game.  I know it’s the perfect opportunity to wear an ugly holiday sweater.  I myself love ugly sweaters.  But when it’s a night out, I want to do better than that.  I know my wife is going to look good, and I for one, do not want to be the fat butch in an ugly sweater standing next to that hot femme all night.  She deserves better.  I deserve better.  These two outfits stay casual with dark denim and boots and also stay on the classy end of the casual spectrum with a thin sweater or a wintery blazer.

When you are a guest, remember to bring a few hostess gifts.  A good rule of thumb is to bring your choice of alcohol and flowers.  Remember though, that the hosts are busy coordinating the party, so either bring flowers that are already in a vase, or better yet, bring a small plant.  This set of small poinsettias are small enough to fill an empty corner of the kitchen counter or serve as a centerpiece on the buffet or table.  You can also bypass the flowers/plant altogether and bring some cookies or another food item for the host to enjoy the next day.

Men's Style Holiday Party

Victorinox Swiss Army Waiter Pocket Knife ($14).  Amazon Essentials 100% Cashmere V-Neck Sweater ($65).  Van Heusen Long Sleeve Shirt ($28).   Timex Weekender Chronograph ($37). Solmate Socks – Poinsettia ($20). Wolverine Leather Belt – Tan ($20).  Everlane – The Straight Fit Jean – Dark Indigo ($68).  Anchor Brewing Christmas AleThursday Boot Company Scout Chukka Boot($150). KaBloom Holiday Collection: Set of 3 Mini Poinsettia Plants ($26).

Holiday Outfits - Casual 2 - 2017

Warby Parker Hudson Glasses ($145).  Gold Tone Buckle Belt ($25). Croft & Barrow True Comfort Shirt ($18).   Cavani Mens Wool Mix Tweed Blazer ($140). Daniel Wellington Dapper Bristol 38mm Watch ($114).  GOLD TOE Frankie Striped Crew Socks ($8). Buck Knives 302 Solitaire Folding Pocket Knife ($32).  Rose Rose Gold Metal Lapel Pin ($20).  Everlane – The Straight Fit Jean – Dark Indigo ($68). Captain Morgan Private Stock RumUnlisted by Kenneth Cole Chelsea Boot ($40).  Cheryl’s Winter Wishes Cookie Box ($37).  

Business Casual

Ah, the dreaded office party.  If it’s just your co-workers you may be tempted to slide all the way into casual mode.  If the bosses and higher-ups are attending, you will worry about whether you are dressy enough.  Choosing a plain oxford shirt instead of one with a pattern and a dressier style of chino with a crease keeps the business in business casual.  Dress shoes with a pattern (like wingtips) are the perfect choice for walking the tightrope between dressy and casual.  Lastly, we can choose our accessories to really swing the whole outfit towards either end of the dressy or casual spectrum.  A tie or lapel pin dresses things up.  A scarf or unbuttoned collar keeps the outfit a bit more casual.

Holiday Outfits - Business Casual -1 - 2017

Zenni Optical Square Eyeglasses 322921 ($26).  Alfani Slim Fit Dress Shirt ($33 or $23 with offer code: FRIEND).  Amazon Essentials 100% Cashmere V-Neck Sweater ($65).  Savile Row Leather Reversible Belt ($30).  Dockers Slim Tapered Fit Signature Khaki Pants – Camino Burma Grey ($43).  Orient Capital Version 2 Dress Watch ($112).  Nunn Bush Nelson Wingtip Oxford ($68).  Bold Socks Argyle Dress Socks ($12).

Holiday Outfits - Business Casual - 2 - 2017

Zenni Optical Square Eyeglasses 322915 ($26).  Michael Kors Dress Shirt ($60 or $42 with offer code: FRIEND).  Lauren Ralph Lauren Cashmere-Blend Sport Coat ($180 or $126 with offer code: FRIEND). Stuhrling Original 997L.04 Ascot Dress Watch ($100). Case Chestnut Bone Peanut Pocket Knife ($43).  Mio Marino Fashion Scarf ($11).  Bonobos Stretch Wool Dress Pants ($198). Synthic Apparel Stitched Leather Belt ($20).  Ties.com Snowflakes Tie ($12.50).  More affordable slacks option – Perry Ellis Slim Fit Dress Pants ($50 or $35with offer code: FRIEND).  Florsheim Marino Wingtip Oxfords ($90 or $62 with offer code: FRIEND).  The Tie Bar Circuit Dots Dress Socks ($8).


My wife’s company throws a swanky party every year at a nice steakhouse.  Everyone dresses to the nines and ten years ago when we started attending, I was lost.  I had no idea what to wear.  And I was incredibly uncomfortable every single year.  Worst of all, I was so jealous of the guys in their sleek suits and ties.  Well, I’ve now had ten years of trying variations on outfits that were somewhere between masculine and feminine.  I’ve worn variations like the above business casual outfits that left me feeling a bit underdressed.  Then I graduated to blazers and slacks that worked perfectly when I wasn’t quite confident to pull out a suit and tie.  This year, I can’t wait to go full on suit, tie, lapel pin and dress shoes.  Hell, maybe you feel jaunty enough to pull off a shirt with cuff links or a dinner jacket with silk lapels.  However, this is not the time and place for statement socks or a silly holiday tie.  Lastly, remember you will probably feel worse underdressed than overdressed.

Holiday Outfits - Formal Business 1 - 2017

Zenni Optical Half Frame Glasses # 765921 ($26). Poinsettia Lapel Pin ($21).  Calvin Klein Dress Shirt ($52 or $37with offer code: FRIEND).  Indochino Dark Navy Suit ($379).  Orient Bambino Version 4 Dress Watch ($169).  Italian Leather Dress Belt ($29).  The Tie Bar Pittsfield Plaid Tie ($19).  Florsheim Corbetta Cap-Toe Oxford ($110 or $77 with offer code: FRIEND). Gold Toe Metropolitan Dress Socks ($15).