An early winter work trip
Outfits for when you're basically 30, and it's a little chilly.
Since I live under a rock (i.e. don’t have a TikTok), I’m sure the cultural discourse has already moved on from “how funny is it that young people have no idea how to dress to go to an office”—unfortunately (or fortunately!) I have not moved on. (I actually love some of the bonkers outfits I’ve seen trickle in from TikTok onto my basically-boomer IG feed, but I have no desire to recreate them lol. Cheers to you youngsters!) I’m here today instead to speak on (1) how I like to dress for work trips as an almost-30-year-old and (2) how I pack strategically to account for each look.
What I’ve worn to the office
An entire section of mirror selfies, I feel so 2013.
I arrived to Brooklyn a day before I had to go into the office, so the first outfit had to be something comfortable enough for a 3 1/2 hour train trip, as well as a day of puttering around the city, but not something work appropriate necessarily. Thus, this outfit features:
the Yohji Yamamoto blazer I’ll wear as an outer layer with all my other outfits while I’m in down
a Lululemon pullover and a Lululemon Align bodysuit as my core layer (two items I would not sport at the office)
a pair of frilly socks long enough to stick out of my Allsaints ankle boots (the boots which will also go with all the other outfits)
a Libra necklace from my grandmother, on a thrifted silver chain; my Alicia Hannah Naomi wedding ring <3, a cast coyote spine vertebrae ring, an oversized silver safety pin for closing the jacket (or leaving open), and my Bea Bongiasca x Linda Farrow eyeglasses (originally sunglasses, with my prescription replacing them!) — all of which will be included in every subsequent outfit
and, finally, a Salvatore Ferragamo Gancini top handle bag (spacious enough for a book, my wallet, and all my toiletries — retainer case included lol.) Accessorized with my very-down-market Boba tea keychain to give it a little whimsy.
There is also a suitcase here, not pictured, which is European carry-on sized. So, small! Helps me from overpacking to limit myself to that and my purse when on work trips.
The Lululemon items are here for comfort; Amtrak is lovely and the seats are generous, but it’s still a travel day and I want to be comfortable more than anything! The blazer fortunately doesn’t easily wrinkle (being a synthetic/natural blend helps) but I would iron it in the hotel if needed. If the weather had been a bit colder, I would’ve likely had a knee length puffer coat on this journey, but it was unseasonably warm, so I skipped it.
Wearing the shoes I’ll be wearing for the other 3 days also opens up a lot of suitcase space, so I opted for boots that were comfortable but fit in my style plans.
The next ensemble was my first day in the office in quite some time; so the blazer, boots, jewelry, and purse all come along for the ride again. Newly added are:
Pleats Please (Issey Miyake) short sleeve top
Skims long “slip dress”
I’ve waxed poetic about the Pleats Please line before, and I need to once again remind you all that they are so convenient for travel. No ironing, no steaming, no nothing required; you will always look put together. (Scoring them via any thrift/secondhand retailers, even online, is also easy in a way that other items aren’t; the sizes are really generous and the quality is pretty guaranteed to mean you always made a great investment.)
The Skims dress is perhaps a controversial choice. Anything Kardashian-connected is inherently controversial, but even more so is the idea of wearing a “slip dress” to work. I’ll make my case: (1) the dress is being misrepresented as a slip dress and (2) a slip dress is undergarment coded, but can be styled to look much less so.
For (1) — this Skims dress is a light, but dense knit. Even stretched over my stomach or legs, it isn’t revealing; you can’t see underwear underneath it (at least in the black colorway) and that makes it acceptable workwear in my opinion.
For (2) — the spaghetti straps are being obscured by the top layered atop the dress. This also helps style the dress in a way that is office appropriate. We can fight all day about why women’s shoulders aren’t work “appropriate” and I fully agree that it’s bananas that you won’t feel “professional” wearing spaghetti straps at work; but here we are. This isn’t the specific fight I wanted to fight this week; so, spaghetti straps obscured. Check.
The next outfit once again included the blazer (not pictured), jewelry, and boots. The rest of the ensemble included:
Pleats Please (Issey Miyake) long sleeve top
Marc by Marc Jacobs trousers
This outfit I love because of how bright and jewel-toned the top is. It just makes me happy to hit those sculptural and colorful parts of my style sense in an outfit. Once again, the logic here was to pack something that wouldn’t wrinkle and would look “put together” instantly. This hit those boxes; the trousers in particular “roll” well and those pleats go nowhere, as we know.
The last day had to take me into the office and back onto the train, so I wanted comfort but needed to maintain that dash of professionalism. Once again; blazer, jewelry, and boots made a reappearance and the new kids on the block were:
a Max Studio just-above-the-knee length knit dress
fleece-lined leggings from TJ Maxx (hello, fellow maxxinistas!)
This dress is such a trusty staple to my wardrobe. The perfect length; very transitional, dressy but not too dressy, and comfy. Fleece-lined leggings, naturally, were added for comfort and thermal management lol.
How I packed it all (and what else got packed)
Since I only had 22 x 16 x 9 inches of packing space; the name of the game here was “what can I use more than once and it won’t smell terrible” and also “what can I include as backup”.
I took a few cues from Joan Didion (a popular reference it seems these days!) and just tried to include the absolute least I needed, with coverage for something getting stained.
So the packing list ended up looking like this, for a 3 day trip:
Suitcase:
2 shirts
2 dresses; one long - one mid-length
1 pant
1 pair of leggings
3 pairs of undergarments
3 pairs of socks
1 alternative pair of shoes (black boots, but sans-silver hardware)
1 alternative blazer/jacket (a Sonia Rykiel wrap jacket)
work laptop
Purse:
bag with: retainer, toothbrush, travel toothpaste, floss, prescriptions, deodorant, hand cream
iPad (for personal entertainment)
keys
wallet
a book and a pen (to markup any quotes or observations)
Unlike Didion, I aimed for things that felt uniquely mine, but still suited to the vibes of my work environment. (For context, it’s a tech startup, so it’s pretty lenient, but my personal feelings about being “at work” have me considering certain constraints, like avoiding bare shoulders.)
I have enough pieces that match these descriptions that I could recreate this list probably 2 or 3 times over, across the seasons. I might add a piece or two for a longer trip, but the interchangeable and mix-and-match nature remains no matter the length.
My only advice for “packing light” is to look at your trip length and be ruthless. Only pack alternatives for things that are likely to totally derail your life if they get messed up (e.g. shoes that get destroyed, or a warm layer getting forgotten somewhere). If I get a stain on a top, I just deal. Maybe not the most practical advice and others might disagree, but that’s how I do it! (For a slightly different take on strategy here, I like this advice from Christina Mychas.)
It’s been a minute since I last wrote, so it felt good to get back to it. I’ll be back again, maybe with holiday hot takes? We’ll see!
xoxo JM, lol.