This week, a reader submitted question:
Dear Bruce,
I have a new event to prepare for in roughly 3 weeks. We have been invited to a casual dinner with other parents from my kid’s preschool. My wife wants to be friends with the couple hosting, and one of them is an architectural designer (and both of them are always well dressed).
The event is on a Wednesday night and it has been billed as “a very casual dinner at our house. All are welcome: siblings, nannies, visiting grandparents, etc.”
I want an outfit that will make me look well put together without being “dressed up”. The event is supposed to be casual, there will be kids, including my toddler, there so things will likely get messy, and my wife isn’t getting more dressed up than jeans and a sweater.
What do you think I should wear?
—Harrison
Welcome to A Well Worn Dispatch, an at-least-weekly newsletter about dressing well, feeling good, and giving a damn. With an emphasis on style that’s personal and a focus on intentionality and craft, I answer reader submitted questions and invite you to go window shopping with me for the finest jawns the internet has to offer.
Harrison, I love this question, thank you for sending it in.
I firmly believe it is better to be overdressed than underdressed. That said, you can be too overdressed for a situation and that can make you stand out a bit too much for your own comfort.
Despite being a “casual” event, the fact that it’s on a Wednesday after work gives you a nice range of dress to play in. And, now is the perfect time to bring out your fall colors and textures.
I’ve built a few different fits you can throw, depending on how far into casual you want to push things. They are all built around the same shirt and pant combo (and even these give you some leeway).
I know you want to look good for this event, but more importantly, I need you to feel good in what you wear for this. If you’re uncomfortable in what you’re wearing it’s going to show in your interactions with all the people you’d like to make a good impression on, so it’s imperative that these clothes aren’t wearing you. That said, if something in these suggestions feels like a stretch, you don’t have to wear it. Or, practice wearing it some day before the actual party, that way if you decide to go for it, it’ll feel a little less foreign when it’s time to wear it for real.
The Supporting Cast
The base of this outfit is intentionally simple (almost overly simple), and likely something you’ve already got in your closet.
The Shoes: A leather boot (chelsea, chukka, or work) or loafer (penny or tassel). Brown or black will work here, and I’ve included both in the example images. A darker suede can work here too, but given the potential for spills, best stick with leather.
The Pants: Chinos in grey, olive, or khaki, or medium to dark wash denim. This sort of event is normally the perfect place for some white or natural denim or chinos, but given the children running around (your child included) it’s best to avoid these lest you end up with a…memorable stain.
The Shirt: Tucked into those pants go with a poplin spread collar in blue or white (a stripe would be perfect here, and I’ve got just the one). A classic OCBD (oxford cloth button down) would also work here.
Optional Accessory: A knit tie in a fall hue (yellow, burgundy, olive, brown) or a navy if you’re feeling a little more reserved. Not all of the following outfits will work with a tie, but a number of them will.
We are keeping these simple for a reason. Assuming your shirt and pants fit you well enough, no combination of the above will look bad, and this would be a perfectly acceptable outfit to wear all on its own.
But, we’re not here for perfectly acceptable, we are making memorable first impressions, so the shirt, pants, and the boots are the supporting cast for this fit.
The Stars
Since this is a Wednesday night party, you might be coming straight from the office, so to me, a blazer isn’t out of the question. But it needs to be something with a lot of texture and it probably shouldn’t be navy or charcoal grey. That will help to bring the formality down a notch or three. Now is the perfect time for a tweed, donegal, corduroy, or houndstooth. I know I mentioned a knit tie earlier, but I wouldn’t wear this with a tie because that’ll be a little too formal for a weeknight-child-friendly-dinner-party. If you’re feeling particularly bold, swap out your dress shirt for a knit polo sweater like the outfit on the right above.
If a blazer feels like too much (or your wife vetoes it for being too fancy), try a cardigan. This could be a thinner knit that you wear with (or without) the aforementioned tie. As with a blazer, make sure you leave the bottom button of your cardigan unbuttoned, it’ll help the sweater lay a bit nicer, and give you a touch more room to move when chasing after a kiddo. You could also go for something bigger, chunkier, and a little more relaxed (sans tie), which might help you embody a slightly more chill dad vibe, especially if you’re feeling a bit nervous about the whole thing.
Don’t have a cardigan in your closet (yet)? That’s okay! Don’t rush to order one online just yet. Good knitwear is an—often expensive—investment, so It’s often worth shopping for in person if you can to get a feel for the wool. If you can’t get your hands on a sweater in person, I recommend reading some reviews to see how others find the texture of the fabric, and how warm it wears.
If you want to go a little lighter weight, I think this is the perfect time for one of my favorite layers, the chore coat. It will look great on its own, but you can also button it up with a knit tie, almost like a blazer, much like David Coggins did at The Masters (above left). There are so many options for chore coats, from lighter weight linen, canvas, or twill, to warm, cozy wools and cords. Find one (or three, I’m not counting) in a fabric or color you like. A yellow or rust chore coat would pop against the rest of your outfit, or lean into the texture with something like this olive cord from Sid Mashburn. If you’re feeling something a little more symmetrical or your style leans more toward militaria, a field or hunting jacket would work just as well. I could devote an entire Dispatch to chore and field coats, and I will soon.
Maybe you want to wear some knitwear, but aren’t feeling the cardigan look. No worries, you probably have a crew neck or v-neck sweater in your closet. It works perfectly here. Bonus points if you have something in an autumnal hue. In fact, if it’s a particularly brisk evening, you might need this sweater as a layer under the blazer or chore coat. Should you need to do that, think about how the color of the sweater compliments or plays with a color from the pattern of the jacket. If you have questions about this, you can always reply to this email and we can work on the outfit together.
The last top layer option, and perhaps the least formal of the bunch here, is a shirt jacket (or “shacket” which, as much as I love a good portmanteau, I cannot bring myself to say out loud) like a CPOshirt. Modeled after the wool jackets given to Naval Chief Petty Officers, CPOs have two flap pockets on the chest and are often made of hearty wool, but you can find other versions in cotton or linen depending on what you need for your climate.
Oh, one last bonus item if you’re feeling especially adventurous: the rugby shirt. Worn like Marc Briant-Terlet, on the left,over a poplin shirt and tie, some lighter washed jeans, white ribbed socks, and suede loafers, this would be a very cool outfit with a lot of character. No pressure, just something to think about.
Hopefully, Harrison, this gives you some ideas for an outfit you can build for this event, and any other (semi) casual events this fall, from your current wardrobe.
I think shopping from your closet is the best option. If you don’t have a blazer that you think works, don’t rush out to buy one off the rack that you don’t get tailored, it’s better to show up in an outfit that fits and feels familiar than in something new. Almost everything in menswear looks better when it’s been lived in a bit.
I said it up top, the most important thing is that you feel like you. That will give you an extra boost of confidence at this party. Knowing that you’ve assembled your outfit with care is a flex all its own. You’re gonna look damn good, and hope you send me a fit pic of what you end up wearing.
—Bruce