Hey Sid!

Jackets and Jeans

Hey Sid!

You ask, Sid answers

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“I struggle with wearing a shirt/tie/jacket with jeans. Whenever I try this look, I give off middle school principal vibes and don’t stick the landing. (No offense Mr. Feeny). Maybe it’s the shirt, maybe it’s the tie, maybe it’s the shoes, perhaps it’s all of it! You and the Mashburn crew always pull this look off well, what do I need to do to get out of this proverbial detention and pull it off too?” - Benjamin H.

Sid and his daughter, Pauline at a school event. Sid is wearing a textured coat, a blue green tie with a little texture to it, a pale blue dress shirt, natural rinse denim, and a chocolate leather pair of tassel loafers.free of principal vibes, even for school  

Hey Benjamin. I love this question. It’s never a bad time to revisit the fundamentals, but back-to-school season feels especially right. Especially given the look you’re trying to avoid.  

But let me back up and say that you probably look cooler than you think you do. Even for the most stylish people on the planet, some days are gonna feel better than others. That said, there are some things to keep in mind (and things to avoid) in order to pull this look off, so let’s get into the basics of what is a pretty standard outfit combination around here: sport jacket + shirt + tie + jeans. You’re right that the guys in our shops and office rock this look a lot. Especially the younger guys, who are just starting to build out their wardrobes and may not have a ton of suits or dress trousers yet to play with… but I’m also wearing this combination, pretty reliably, about twice a week. Let’s go piece by piece:

Starting at the top. Your jacket needs to have some texture or pattern if you want to wear it with jeans. It cannot look like it’s the top of a suit, so you don’t want a fabric that’s too smooth or solid or flat-looking. No sharkskin, probably no plainweave (except for a navy high twist blazer, which tends to pair nicely with almost everything.) Anything very dressy or smooth does not party well with the texture of denim. I prefer when it feels like “I had a pair of jeans I wanted to dress up,” vs. “I had a jacket I’m trying to dress down.” High-twist wool works well (we make those primarily in solid colors,) but if you’re just getting started with this look, I’d go overboard with the texture while you find your footing. In colder weather, that means flannels, tweeds, herringbones (this new one would be perfect); summer equivalents would be linens and seersuckers. I wear this houndstooth with jeans a ton. Hopsack’s another great one. Actually, a really good four-season option for this is our monk’s cloth. If you’ve been with us for awhile, this is the fabric formerly known as leno. It’s a story for another day, but we finally located a mill that has been able to replicate that fabric, and we’re calling this new version monk’s cloth. The mixture of cotton and wool is very versatile, and it’s got the right texture – kind of rustic and nubby – to look really great with denim. I own the jacket in three colors and wear all three with jeans all the time. 

Next up: the shirt. Since you're wearing it with a tie, you really want it to look like a dress shirt. Pattern-wise, think fine stripes, tattersalls, graph checks, solids. Quiet colors. Any loud, big patterns may be overpowering. You can make a sport shirt work if it's pressed and crisp and the pattern is small, but it's probably easier to just go straight to a true dress shirt. (And if you end up taking off your jacket over the course of the day, roll your sleeves. 3.5 rolls is what I usually recommend, pushed above the elbows to avoid the 'waiter' look.)

Brandon in the Atlanta shop getting the formula right.

Then comes the tie. First off, it’s gotta be TIED. No sloppy knots here. Overall, your top half needs to look pretty sharp (hence the dress shirt.) Maybe this is counterintuitive, but to look right with jeans, the tie can’t be too dressy. No Macclesfields or anything too shiny or formal. Are you getting déjà vu from the jacket section? A knit tie is fantastic here, as is a striped repp, or anything with cotton, linen, or wool in the mix to give it a bit of texture to jive with the jeans. Different from the shirt, the tie can go as casual as you want… or at least, as casual as a tie can go. In the summertime, a raw silk matka is unbelievable. In the winter, a wool flannel is beautiful. You get the idea.

JB, Josh, and Thomas in the retired green leno weave jacket — here's the new version

Down at the bottom. Just like the jacket and the tie, your shoes should not be overly dressy. Loafers – either pennies or tassels – are great. So are our five-eyelet bluchers. In colder weather, chukka or Chelsea boots are also great. You get a little more leeway with suede, which inherently leans more casual. For example, suede cap-toes work, but leather cap-toes tend to look a little too formal with jeans. Actually, consider that a good shortcut… it’s hard to mess this look up with suede shoes. And while they shouldn’t be too dressed-up, they should be clean and tidy. That means polished for leather, and clean/brushed for suede. One majorly under-appreciated way of keeping your shoes in good shape is shoe trees. I cannot overstate their importance when it comes to preserving the life of your shoes. Even if you just start with a single pair of trees and rotate them out, that will help a ton. Take your shoes off when you get home, let them air out and rest for a few hours, then put the shoe trees in them before you go to bed. If possible, give them a break between wears and don’t wear the same pair two days in a row… which will give the trees about 48 hours to do their thing. This concludes my commercial break for shoe trees. Bottom line: keep your shoes neat and not too dressy.

a seasonal riff

Oh, yeah, and of course… the jeans themselves. This may go without saying, but they should be in good shape, with no tears, minimal to no distressing, a clean hem. Length-wise, they shouldn’t be too long — y’all know I like no break on mine, but a slight break is fine if that’s not your thing. No stacks. Anything too saggy and baggy doesn’t look right with a jacket to me. Also, as much as I love true indigo, you don’t have to limit yourself to blue jeans. White is great, natural is great, and both are great blank canvases for a sport jacket with some zip to it. Once you get the hang of the basics, try branching out with some colored denim or canvas.

Jacket + jeans + tie (and sweater + jeans + tie on Jonathan) at the World Series parade

Finishing touches. You want a belt. A D-ring or woven works here, but if it’s made of leather or suede, it should be in roughly the same color neighborhood as your shoes. That subtle hook-up is going to make the whole look feel cohesive. And speaking of cohesive – throw in a pocket square. Nothing too dressy or loud. White is always safe. The hem-stitched one might be the biggest, smallest, no-brainer we make. Now that I’ve laid all that out, the thesis here is striking the right balance between casual and formal – and of course, making sure everything fits and is in good shape. In short: make sure your jacket has some texture, make sure your shirt is crisp, make sure your tie and shoes aren’t too dressy (but also that the shoes aren’t too beat-up, either – you’re going for a happy medium.) Minimal to no break on the jeans, with a clean wash… and you’ve got this, Benjamin. No more detention. Good luck!

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