Dressing up is fun, right? You get to prance about in your fanciest of jackets, that most luxurious of shirts, your most esoterically welted shoes. But, unless you’re going to a royal gala, it won’t take long to feel a little out of place decked out in your most precious duds as you stand next to someone wearing double-knee work pants. It’s not to say dressing up is wrong, per se, but going balls to the wall on your finest wares can be a bit ostentatious or just generally out of place. There are ways to incorporate dressier elements to a more casual outfit, and there are some easy things to keep in mind to ensure you’re doing it right that fall between a shirtless and suited Jay Z and the “regular guy politician” look of suit jacket and dad denim.
First, some basics. There are some fundamentals to formality, things which outright signify that they are designed for more special occasions. For instance, the less adornment you have on your shoes, the more formal they are. This means that bluchers or brogues are less formal than wholecuts or cap toes. Most of your clothing has some element that makes it easy to read formality. Pointier collars are more casual than spreadier. Patch pockets are more casual than jetted. So when considering dressing down a more formal item remember that you can’t take something from 100 to 10 so easily. You won’t make the “casual tuxedo” a thing, despite how rad the Rat Pack homies looked all disheveled and coked out after a Vegas stint. Bear this in mind when you look for, say, what blazer you want to keep caszh.
Let’s start with the utmost of dressiness: the suit. You won’t really get away with turning a job interview or sober occasion suit into something more fun-time. Those heavy navies and blacks will make any attempt to lighten them up feel like you’re trying to put the “fun” in “funeral.” But if you have a lighter suit, or one made of a lighter fabric like cotton or linen, then no reason to limit yourself to button up and tie. People like Tommy Nutter were deconstructing the formality of a suit over half a century ago, so you have options to explore. Wearing a spread collar shirt without a tie can look a little peculiar, but with a point or button-down collared shirt, especially one with a bold pattern, you can go for something professional casual, looking like a college professor, or maybe whatever a “brand manager” is. For a real Amalfi coast feel put on a polo, maybe not the preppy pique kind but something of a softer weave (*cough* liketheoneswesell *cough*). Pair with a pair of your preferred loafers or maybe some Chelsea boots and you’re king of the weekend.
Now let’s look at a suits’ individual components: jacket and trousers. There are so, so many kinds of odd jackets and blazers out there that you’ll have to make a judgment call at some point. Generally more patterns equals more casual, with exceptions for things like Prince of Wales or pinstripes, those banker sort of looks. But so long as your jacket doesn’t look like it’s an orphan from a suit you can do plenty of mixing and matching with trousers of contrasting patterns or fabrics. Mixing fabrics is always a hard and fast way to come off as less fastidious. Personally I think there are way too many patterned pants out there with guys looking like they’re the second trumpet for a ska band, so try working more with colors instead of checks and stripes, unless you’re preparing for an emergency skanking dance party.
Maybe you saw this coming when the theme of the week is dressing down fancy items, so here comes my thoughts on jackets with jeans. Not that bad! It’s just that people forget the details and end up looking like a schmo. See, the 90s casualification of everything made most mens’ pants feature a lower rise, denim included. Watch Road House some time and marvel at how close Swayze’s jeans get to his belly button. If you’re going to wear jeans you’re best served by finding some higher rise denim, especially if you’re going to be tucking in a shirt. If you’re not tucking in a shirt don’t do a button-up, you’ll look like you’re having a rough happy hour pity party. Tuck in the shirt, have some fun with it, or return to polos or, hell, a rugby or even crew neck tee for a sort of Bistro Vibes look. Embrace your inner Kevin Bacon.
As for shoes, well, I got to ask- why you trying to dress down your shoes? If you’re busting out your finest Edward Green wholecuts for a trip to the grocery store I’m more confused and amazed by your cavalier attitude towards shoes that cost up in the high four digits. Your better bet is to just read the formality we talked about earlier. Casual shoes are the fastest way to diminish the formality of any outfit and it’s very hard to work in the opposite direction. Wear those Edward Greens with shorts and a tank top and, well, I don’t even know what we’re doing. But putting boots under a suit can look much more reasonable. That suit and sneakers look is, well, fine. I just think it’s trying a little too hard to be some kind of “downtown cool” but more often than not you end up looking as cool as downtown Newark.
I guess last element of a normally dressy look is a tie. This one is hard because it’s both well trodden territory but that’s never mainstreamed. You had rockers in skinny ties, 80s brats with ties over polos, mustachioed baristas tucking ties into their shirts, but it was never adopted by a larger population. Your options are evocative of some sort of very specific look, so if you want to indulge that aesthetic then you probably don’t need my guidance to do your best Fast Times or The Strokes costuming. Back in the day I used to wear a knit tie under a denim jacket, like I was about to be summoned to play rhythm guitar on a Kings of Leon tour. They never called.
That should just about cover it. Don’t let your finer items gather dust in your closet, waiting for a wedding or court appointment so they can see the light of day. Find ways to mix and match, making a few errors along the way, until you find that Goldilocks just right balance. Or just also rock a mullet when you’re mixing up clothing formalities. You’ll keep them on their toes when you’re business in the front and party in the back, but also business on the top and party on the bottom. Maybe business on the right and party on the left, too.