What to Wear on a 24 Hour trip

The other day I found myself in a familiar stressful situation: I arrived home from work at 6:30 PM and had a plane to catch in less than two hours. And I hadn’t packed yet.  
Crazy, I know; packing procrastination does that to you.  For a dizzying moment, I felt overwhelmed, trying to visualize outfits with my closet content revolving in my mind like a tie organizer.  And then I thought: what if my choices were limited?
My trip wasn’t long – just a little over 24 hours from the time I board the plane to the moment I touch down from my return flight – and it wasn’t as I had to pack for a vacation. I just needed to be comfortable enough for the flight down, an all-day assembly the next day, and the return flight home.
Why waste time fretting over different outfits if I could make one outfit last 24 hours? 
Can one outfit last 24 hours?  

what to wear on 24 hour trip menswear sport coat tailored

Sport Coat: Spier & MacKay

Shirt: Finamore

Pants: Rubinacci

Shoes: Alden

Belt: W. Kleinberg

Pocket Square: Drake’s

Tie: Drake’s

Scarf: Drake’s

Here’s what I chose: 
For sheer flexibility, nothing beats good old gray flannel trousers – mid-grey to be precise. You could wear them from the boardroom to the bedroom and no one would bat an eye. They’re like dress sweats, with a crease and a fly. I grabbed an alligator belt to cinch them up.
A jacket, of course, is a no-brainer. You want to have easily-accessible pockets to stash your boarding pass & ID that you’ll be taking out a million times to show every TSA agent in the airport. Get yourself the right sport coat, one that you can dress up or down, and you can take it anywhere, from meetings to martinis. The all-purpose navy blazer is the obvious choice, but it’s not the only one. I really like this classic tan gunclub from Spier & MacKay. The houndstooth pattern is casual without being crazy, and being a shetland wool tweed, its looser weave makes it feel more like a cozy sweater than a rigid jacket. 
Instead of a blue oxford cloth button-down shirt, which is the fail-safe option, I chose its slightly more stylish cousin, the dark chambray spread collar shirt from Finamore. I like how the darker color and twill weave pair particularly well with tweed jackets. Plus, it’s a fantastic fabric. My wife says it’s denim, but I can’t say that I agree, because then I’d have to explain why I’m recommending a denim shirt to meetings. Just say “chambray” and you’ll stay above reproach.
Everyone always says loafers are a good choice for airports, and for good reason: you can easily slip them on and off at security and in the plane, and they go equally well with dressy or casual outfits. If you have a high instep though, the band on the vamp of traditional penny loafers may cause a bit of discomfort when worn for an extended period of time. That’s why I chose tassel loafers – they generally have no band.  And while I do have cordovan tassels, I grabbed my suede pair from Alden. For sheer shoe comfort, suede tassels are tough to beat, and I find they go well with flannel trousers and tweed jackets.
Leaving to catch the plane, 7 PM Friday evening
peter 24 hours same clothes
I wore this on the plane knowing I’d be wearing this not only on the flight down, but at the assembly as well, which meant I had to choose accessories. For ties, you’d be hard pressed to find a one more versatile than a dark solid silk knit. The crunchy, nubby, slightly shiny texture plays well with everything from plain worsted suits to busy sport coats. As I recently gave my navy one away (as a hint to a bro who painfully tries to mix patterns), I opted for a dark green one instead. That, as well as the matte silk/wool square with a large pattern I grabbed to complement it, are both from Drake’s.
At the assembly, noon Saturday
After the assembly, I would get rid of the tie and square and exchange them for a scarf. Of course, I could’ve just loosened the tie, but I’m not one of those guys that wear a tie just because. Ties signal a recognition of seriousness or solemnity; don’t dilute their meaning by just wearing them willy-nilly. When the situation calls for it, by all means, tie up and show respect. Otherwise, adorn your neck with a scarf.
For those of you with a penchant for crazy ties but know better, this is your opportunity to give in – a little –  to your ornamentation fixation. This one is from forum member X of Pentacles, and is the perfect pattern and color for a casual scarf; it stuffed easily in my briefcase, along with my tie, square, and an extra pair of unmentionables.  


Getting ready to fly home, Saturday evening


In retrospect, I think the experiment went well.  I was never uncomfortable in my clothes, and I had everything I needed to be presentable; that much I expected. However, what I didn’t expect was the weightlessness of it all.
All the familiar stresses of travel were gone. Having everything in my briefcase meant there was no luggage to lug around to the check-in counter; not even a carryon to heave and stow in the overhead bin. When I arrived, there was no need to wait by the baggage claim; I just left the terminal and got an Uber. The next morning there was no time spent deciding what to wear because I had packed only one choice. And after the assembly I didn’t need to organize my belongings; I simply picked up my briefcase and left for the airport. In the end, I realized that eliminating options wasn’t restricting – it was liberating. 
Maybe there is something to living a simple life after all.  I should think about that when I order my next suit.
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Peter works in construction, but has an extensive collection of custom suits which he gets so that he can wear suits on the weekend. Even though he lives in San Francisco, he has never used the word "impact" as a verb. He writes about classic menswear and is one fedora away from being a complete dork.

15 thoughts on “What to Wear on a 24 Hour trip

  1. Ciao Peter,
    ottimo articolo.Che tipologia di bagaglio usi,in queste situazioni?


  2. (In english)
    Hello Peter,
    excellent article. What kind of baggage do you use in these situations?
    Travel bag, trolley?


  3. I’m hoping you at least packed a few fresh undies. All this brisk efficiency is moot if things start getting a little rank.

  4. Glad to see the tie, but I don’t see wearing a tie as signalling seriousness or solemnity – I simply dislike the jacketed-but-tieless look! Except when I wear a roll-neck jumper with a sports jacket (in cold weather) I would never wear a jacket without a tie.

  5. What about toiletries – toothbrush, toothpaste, etc?

    Chambray is too casual for flannels, and button down would have been better to keep your collar points from sticking out. Also, the tie is too heavy unless you were in a cold weather area. And I’d have gone with a solid pocket square. And a scarf? Really? Who are you, Howard Stern?

  6. Ciao Mario,

    Stavolta ho usato solo una valigetta. È abbastanza grande per calze, intimi, l’iPad, le chiave, il portafoglio, la cravatta, la pochette, spazzolino da denti, dentifricio…tutto quello che si serve per 24 ore 🙂

  7. Hey TreyByDay,

    I didn’t mention underwear, because, well, that’s kind of a given. Except when visiting nudist colonies, so I’ve been told.


    To answer your questions:
    1) An assembly is an religious event held by Jehovah’s Witnesses a couple times a year, and
    2) For the first second after I put them on, yes.

  9. Hey Alan,

    As it currently stands, wearing a tie signals social queues, which you are entirely free to disregard 🙂 That’s not to say it doesn’t look good. It’s just…too much. Like a monocle.

  10. Greetings Luke,

    I own two types of chambray: a rough one that I wear for work in construction, which I would never wear with flannel trousers. The other is sleek and soft and pairs quite well with them.

    Silk knit ties are fine in all weather except where it’s too hot to wear pants. Global warming may have affected your judgement, but certainly not springtime in Ontario.

    Regarding scarves, I haven’t seen a picture of Howard Stern in 20 years and find it a little charming that you know what a radio personality wears. But go ahead and keep your hobbies. Perhaps report back with a description of Casey Kasem’s wardrobe.

    You speak of button downs collars as though they are the only types that stay under your jacket lapels, but certainly you must be aware that other collars, with long enough points, are perfectly hidden. Indeed, the pictures demonstrate that admirably. In fact, I wonder how you could have even typed your comment, since you clearly must be blind.

  11. Chambray is a good choice. I also like a fine weave denim for Fall/Winter. It looks perfect with tweed such as yours.

  12. Nice read, the outfit looks great on you.
    I wouldn’t wear tassels but that is just because I wouldn’t buy them either 🙂
    Write more!

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