Last Dispatch was the first half of an answer to a reader question asking about ways to be a little less "Business Steve" when off duty. Specifically outfits built around a chore coat, tee shirt, and chinos.
This got me thinking about something bigger than just tee shirts and chore coats.
I did a little digging with Steve and learned that, to his wife, collared shirts equal "business" and they are seen as too fussy or uncomfortable for an off hours dinner date.
I don't think that has to be true. In fact, I believe that collars can be cozy.
It seems to me that many men default to tee shirts and hoodies because they believe that collars are uncomfortable. I think that this idea comes, in part, from their history of being worn for "work". For most, work can be (or is) an uncomfortable or unpleasant necessity, and—without getting deep into the history of collars—for a long time collared shirts were part of the uniform to do that uncomfortable work in.
By the transitive property:
Collars are worn for work.
Work is uncomfortable.
Therefore, collars must be uncomfortable.
I think it's time to change that narrative. Collared shirts do not have to be uncomfortable. In fact, I do much of my lounging in shirts with a collar.
Change the Context
If you want to wear your “business” clothes, do it, but change the context that your OCBD falls into. Keep the same chinos or jeans, but instead of a cashmere or merino sweater sub in a classic cotton sweatshirt. I don’t mean the one you wear to the gym, but something worn in—maybe a vintage one from a place you visited as a kid or even a Polo Bear—is totally fair game. Swap your dress boots or loafers for a work boot or a hiker (don’t get too Gorpy tho), or a simple sneaker.
It is important we not look at any one item in our closets in isolation (unless you have a sweet boilersuit, in which case, tell me where you got it from because I really want one). Each piece in an outfit plays with or against the other pieces. That blue dress shirt isn’t just a business shirt. You can wear it with a wool trousers, a blazer, and (gasp) a tie for an interview or meeting on Tuesday, with chinos and a sweater for a Friday night date, and (in the summer months) untucked with shorts by the pool. Don’t believe me? Check the imitable Sid Mashburn himself below. Same graph check shirt left and right.
Unless you’re Winnie the Pooh, you’re not going out in public wearing only a shirt. So much of menswear flexes across a wide range of formality. The way you put pieces together determines the formality of your overall fit. In this case, less formal pieces like the cotton sweatshirt and a chunkier boot dress down that OCBD.
Find Cozy Collars
A shirt with a collar does not have to mean the stilted, starched, stand collars you might associate with working stiffs of old. There are plenty of casual collars that will help you look and feel good off duty.
First, the cut of the shirt will help make things more casual.
Reach for a western shirt, a long sleeve wool polo, or a rugby shirt. Each of these have details that make them inherently more casual. Wool polos and rugbies (that is supposedly the correct plural but I hate it) have their half plackets and softer unstructured collars. I highly recommend wearing one with jeans, white socks, and tassel loafers on your weekend coffee run like AWWD subscriber Tucker (below).
Western shirts (my favorite of the bunch) have their…well…western yokes on the back (and sometimes front), unique pockets, and best of all, pearl snaps
If the temperature has dipped, or you feel like layering a bit more, there are some mid-weight shirts that you could work into rotation here. I’m thinking work shirts, shirt jackets, or CPO shirts.
These all follow a similar pattern: cut like a shirt with more room for a layer underneath, spread collar, often two chest pockets—sometimes with a flap or extra detailing like a pen sleeve, and made of heartier fabrics like slubby denims, twill, or wool. With their origins in workwear or the military (CPO stands for Chief Petty Officer) these are definitely a little more casual—despite the CPO being something worn by Naval Petty Officers on duty.
Once you settle on a shirt cut (or maybe two), now comes the fun part, introducing variety with fabric texture and color.
Hearty fabrics like tweed, moleskin, corduroy, flannel, and twill are all great choices for an off duty wear. I’ve included some examples for you here.
If much of your closet is solid colors and muted tones, this can be a great place to inject more color and pattern into your wardrobe (see the mostly red examples above).
Remember, the brighter the color and/or the bigger the pattern, the more casual the piece. Go with bolder, richer colors that might be a stretch for your comfort zone, a turquoise or yellow western shirt, a bright red rugby, or a wool polo in a beautiful burgundy. If you’re feeling adventurous, opt for a big pattern like a plaid or check. Make sure the pattern of the pockets matches with the shirt body if that sort of thing bothers you. Tweeds can give you patterns like glen plaid or houndstooth, a great place to pull in accent colors that complement or contrast with the rest of your outfit.
TL;DR
Clothing is Contextual
The items in your closet don’t exist on their own. They are always read with the context of everything else you’re wearing. If you want to wear something because you feel good in it, chances are, you can dress it down with a more casual supporting cast.
Find Your Cozy Collars
Soft fabrics, brighter/richer colors, and patterns (the bolder the more casual) are all great ways to dress down your looks.
Try Lounging in Your Collared Shirts
Collars aren’t just for business. To break that stigma, instead of changing into a tee shirt and hoodie at the end of the work day, dress it down: try cooking dinner and lounging about in your collared shirt. In this case, you’re changing the context (see 1.) of where you wear the clothes, even just for yourself.
Like always, if you have any questions about clothing contexts or need a fit check, reply to this dispatch and we will chat.
—Bruce
Is AWWD subscriber Tucker single??? 👀👀