Dress Code: Ambiguous
No Career Limiting Party Fits
November is the start of real Holiday Party Season. You’ve made it past Halloween parties, now it’s time to wear something that hopefully feels less like a costume. Unfortunately, what sometimes comes with holiday parties of the work variety is ambiguous dress codes.
Let’s tackle one of the potential dress codes you might see, “Business Attire; tie optional.” I don’t even want to open the can of worms that is “business casual” party attire, so we will leave it for now.
Holiday parties can get weird. It’s a time for people to make awkward small talk with their colleagues and their plus-ones, and after one-too-many beverages make the occasional “career-limiting decision.” Let’s keep your fit from being one of the latter.
I will continue to beat the drum of feeling like you in what you wear, and ideally that makes you feel good. You must be comfortable in your clothing, but remember that comfort doesn’t have to mean stretchy pants and hoodies. I’m all for cozy comfort, but a holiday party isn’t the place to look like a millennial at the airport (you’ve seen them, and you must know I have lots of thoughts).
I have three recommendations for lead singers1 (an idea I will continue to borrow from the ever-stylish Sid Mashburn) to your outfit:
Statement Jacket
Statement Trouser
Fun Suit
Statement does not have to mean loud. I am not suggesting you show up in bright red trousers. If you want to do this, and you already have the pants, you probably don’t need any guidance from me, but know that I fully endorse this.
What these three leads do is keep you from wearing a typical navy or charcoal suit and having your tie do some very heavy lifting of singing lead. As much as I love ties, I’m leaning heavily into the tie being optional part of the dress code in my advice right now.
Statement Jacket
I think a statement jacket is the lowest risk option, and if you don’t have any of these three options in your closet already, this is an easy and versatile place to start. This jacket is not a navy blazer, or a charcoal, grey, or navy suit separate jacket. Those are perfect for the second fit, but a too simple to be a statement here. We’ve established what this jacket isn’t, so what should it be?
There are a number of ways your jacket can make a statement, beginning with the fabric. For the cooler temperatures, I would pick a tweed base in a brown, green, or grey. From there, it’s all about patterns, and the textures that come with them. On the subtle end you’ve got donegal and herringbone, then houndstooth, windowpane, and small check in the middle, and bigger bolder patterns like glen plaid, big checks, and tartan. This is the perfect opportunity for a classic jacket cut: the 3/2 roll, or if you’re feeling particularly bold, a double breasted.
If I were going for a quiet jacket, I might pick something like this Hopsack Houndstooth from Sid Mashburn. From far away it reads as just a brown jacket, but when you get closer you see the wine color that makes up the houndtooth and it gives the jacket a lot more depth. For something bolder, I’d go for this Rally Tweed Waverly from J. Mueser because it has tons of colors in the plaid pattern to play with.
With a jacket like this the backing band for the fit can be very simple. Grey wool trousers—four season high twist wool or a wool flannel—are the perfect choice. A white Oxford or poplin shirt—spread or button-down collar—doesn’t draw attention away from the jacket. Should you want to wear a tie, a knit in burgundy, oxblood, orange, or the always classic navy will do nicely. Or, you can pull a color or two from the pattern in your jacket to play against a larger or smaller pattern in a tie. If you’re in a pinch, you can email me and I can help you pick what might work.
Statement Trouser
A statement trouser isn’t that different from the statement jacket, but if you’re not used to your pants singing lead, this can be a little daunting. I totally get it.
As much as I’m an advocate for white denim, this is not the place (unless you’re on some top level Observer shit).
The same rough idea as with the jackets above applies here. Focus on the same fabrics and patterns from above in brown, grey, or green. A lot of the places from above sell matching pants (to make a fun suit, we’ll get there I promise) as separates. They are absolutely worth getting if you see something that speaks to you.
You can add a little visual interest to the shirt with stripe or a small check here if you want. Blue, pink, or lavender would work a treat. And for your (optional) tie, if there’s a color in the pattern of your trousers, pull something in that complements or contrasts it.
A Fun Suit
The last option for your holiday party is my personal favorite. For me the fun suit is for big, bold patterns: glen plaids, big windowpanes. This is also a great place to try out a double breasted jacket. Or an extra flex, a double breasted Prince of Wales.
Instead of a tie, I would pick something like a denim or chambray shirt, or maybe even a roll neck sweater (above left from Aimé Leon Dore). The denim shirt provides a formality counter point to the suit, while a roll neck complements it. Both work beautifully.
If you’re feeling really festive, maybe toss on a wool/silk scarf. I want all of the Drake’s scarves. They’re whimsical and weird and perfect.
None of these statement pieces have to be limited to party-attire. In fact, I would encourage you to work these things into your weekly rotation.
The point of all of this is to have fun! It is a party after all. If you want some non-suiting ideas, I’ll point you toward Drake’s excellent Autumn in Paris Lookbook for the incredible layering and pairing of ties with non-suiting jackets (a favorite of mine).
Got holiday dress codes that are baffling you? Let me know in the comments and we can tackle a fit together.
“You want to have one element of your look that's your strongest piece, and everything else is singing backup.” —Sid Mashburn