December 15, 6:30PM, I stood in the Red Line station. I was wearing a Theory blazer and what I thought was the perfect Christmas Party Look, a Banana Republic sequin top. By the time I reached Back Bay, the sequins were snagged on everything (coat zipper, subway pole, etc.) and my tights were developing a run that seemed to grow with each step. My heels, which I thought I could wear for a short commute were now actively rebelling against my feet.
While trying to text my coworker Maya about being late; and trying to prevent my blazer from getting wrinkled on the subway, I realised I looked EXACTLY like I was — a finance professional, who had dressed for a party in her Beacon Hill apt. and then had to navigate Boston Public Transportation. This is NOT a good look.
That night — I ended up in emergency flat shoes purchased at CVS; and spent half of the party trying to safety pin my top back together in the restroom. I made a promise to myself. I work too hard. I spend too much money on clothes. I will never again show up to a work function looking like I went through a blender.
There had to be a way to dress for these corporate holiday events, and not have to sacrifice looking good, or arriving in one piece. So, I spent most of last winter testing different approaches. Every work event/client dinner became a lab for party-professional wear that could endure the T, Boston Weather, and my tendency to spill things on myself.
1st Lesson Learned: Layering is Everything. BUT, layering MUST be Strategic. What I call “Defensive Dressing”. Your base layer MUST be able to WICK MOISTURE. Commuting on a heated subway car in Winter = Sauna. I found these Seamless Long Sleeve Tops at Uniqlo. They are thin enough to disappear under your real outfit. However, they keep you from FREEZING when you inevitably have to wait for 20 minutes for an Uber outside the Venue.
Middle Layer — the part people ACTUALLY SEE — was harder to find. Anything with Loose Sequins/ Beading = DISASTER. I learned this the HARD WAY when half the embellishments fell off a Zara Top during ONE of the most Crowded Rush Hour Commutes EVER. Now, I only buy items with Sparkle that is WEAVED INTO THE FABRIC, NOT GLUED ON TOP.
My current GO TO is Navy Knit Dress from COS with Metallic Threading. SOUNDS BORING — I KNEW THAT WHEN MY ROOMMATE ASKED IF I WAS GOING TO A FUNERAL FOR A ROBOT when I first brought it home. Under party lighting — IT IS STUNNING. AND MORE IMPORTANTLY — I have worn it to FOUR DIFFERENT EVENTS THIS SEASON. IT STILL LOOKS PERFECT. AT $120 — it was not CHEAP. However, considering I have ALREADY GOTTEN MORE WEAR OUT OF IT THAN MOST OF MY “SPECIAL OCCASION” PIECES — the math WORKS.
Separates — I found Success with Black Velvet Blazer from Theory. ($285) Made Me Physically Ill. BUT — TWO YEARS LATER — it is STILL my #1 PARTY PIECE. The Velvet is THICK ENOUGH to hold its SHAPE when CRUSHED AGAINST OTHER COMMUTERS. AND — it automatically makes WHATEVER YOU WEAR UNDERNEATH look more EXPENSIVE & INTENTIONAL.
Bottom Half Strategy — I had to Test Some Stuff Too. After One Memorable Incident — SILK SKIRT + RAINSTORM = WET ANIMAL AESTHETIC — I switched to Wide Leg Trousers in Darker Colours. Not BLACK — Shows Too Much LINT/GENERAL SUBWAY GRIME. But Deep Navy/Burgundy. I Found These High-Waisted Ones at Zara with Subtle Gold Threading that adds JUST ENOUGH Festive Energy Without SCREAMING “I’m Going to a Party!” To EVERYONE ON THE GREEN LINE.
Shoe Situation = ETERNAL STRUGGLE. I’ve Tried Bringing Separate Party Shoes — BUT That Comes With Its Own Risks. Last Year I Showed Up to Our Year End Client Event with Two Different Black Pumps because I’d been Packing in my Dark Closet That Morning. Another Time My Backup Heels Got SOAKED When My Water Bottle Leaked in My Bag — Leaving Me With Wet Leather Nightmares.
My Current Solution is Pair of Block Heel Ankle Boots that Can Handle Both Commute & Party. Invested In Some From Stuart Weitzman that Were Painful at $350 — but have Been Worth Every Penny. They’re Comfortable Enough for Walking/Standing on Subway Platforms — but Sleek Enough that I Don’t Feel Under-Dressed When I Arrive. The Key Was Finding Ones that Had Been TREATED for WATER RESISTANCE — Boston Weather Doesn’t Care About Your Party Plans.
Foldable Ballet Flats — If You’re Committed to Full Stiletto Fantasy — Those Are Life Savers. Ridiculous. You’ll Look Like Crazy Changing Shoes in Bathroom of Whatever Venue You’re Attending. But Better Than Alternative. Which I Experienced During Particularly Brutal Client Holiday Party in 2019. I Ended Up Walking Barefoot Through Downtown Crossing Because My Feet Had Completely Gone Numb. Not My Finest Moment Professionally or Personally.
Outerwear — Where I Used to Make Biggest Mistakes. Either Freeze in Something That Looks Good but Provides Zero Warmth. Or, Bundle Up in Everyday Puffer Coat & Look Like I’m Headed to Bruins Game Instead of Corporate Event. After Many Expensive Mistakes & Extensive Research, I Found Wool Wrap Coat from Reiss That Hits Sweet Spot. ($425) Made Me Question ALL LIFE CHOICES. BUT — It’s Roomy Enough to Go Over Party Clothes Without Crushing Them. Structured Enough to Still Look Professional. Wrap Style Means I Can Adjust Fit Depending on What I’m Wearing Underneath.
When I Feel Brave About Weather & Shorter Commutes, I Have Fake Fur Jacket from Warehouse. Emerald Green Colour Gets Compliments From Strangers. Texture Actually Looks Better a Bit Mussed — So Being Squished in the T Works in Favour. Just Don’t Wear It in Actual Precipitation Unless Enjoy Wet Animal Aesthetic.
Minimal Accessories While Traveling. Statement Earrings — Pack in Small Case in Bag Until Reach Destination — After Losing Favorite Pair Somewhere Between Park Street & Office Building, I Don’t Take Chances. Same with Delicate Necklaces — Seem Magnetically Attracted to Getting Tangled in Coat Zipper or Scarf Fringe.
Bag Situation Required Own Strategy Session. Need Large Enough for Touch-Up Supplies/Weather Contingencies. But Not So Massive You Become Person Taking Up Half Subway Car. Settled on Structured Leather Tote That Zips COMPLETELY CLOSED — Crucial After Several Makeup Explosion Incidents. Smaller Clutch Fits Inside for When Reach Event & Want to Look Less Like I’m Carrying Entire Life With Me.
Ultimate Test was Last Month’s Holiday Party for Largest Client. Held at Four Seasons. Cocktail Attire. Naturally — It Was Sleeting. Half the Subway Lines Were Delayed. Freezing. Had to Transfer Twice to Get There. Wore Navy COS Dress. Treated Ankle Boots. Wool Wrap Coat. Carried Cautiously Curated Emergency Supplies — Blotting Papers. Travel Deodorant. Lipstick. Band-Aids for Potential Shoe Casualties.
Arrived Looking… Well. NOT LIKE I’D STEPPED OUT OF MAGAZINE. BUT DEFINITELY NOT LIKE I’D BEEN INVOLVED IN SOME KIND OF WEATHER RELATED DISASTER. Highest Compliment Came from Managing Director, Patricia. Who Pulled Me Aside During Cocktails to Ask How I’d Managed to Look “So Polished” When She’d Seen Me Emerging from Same Subway Entrance She’d Used — Clearly Battling Far Worse Fate Than I.
“Strategic Planning. And Possibly Unhealthy Amount of Thought Put Into Practical Party Dressing.” I Told Her. Right Before Demonstrating How My Dress Did Not Show Wine Stains — BY IMMEDIATELY SPILLING RED WINE ON MYSELF. Patricia Now Asks for My Outfit Advice Before Major Client Events. I Consider That the Ultimate Professional Endorsement.
Truth Is — Working in Corporate Finance Means I Attend A LOT Of These Events — Client Dinners. Holiday Parties. Industry Networking Things. Company Celebrations. They’re Part of Job. And Showing Up Looking Put-Together — Part of Maintaining Credibility in This Industry. But I Also HAVE to GET to These Events Using Normal Transportation. In Normal Weather. With Normal Bags Full of Normal Stuff I Need to Get Through Day.
