First.. the denim
Alright, we can’t really talk about dressing up denim without first talking about the denim itself and making sure we understand what denim looks best. In my opinion, if you’re going for an elevated casual look, a darker wash pair of jeans with minimal distressing is going to look the best.
Light wash or dark wash
The lighter the wash, the more casual the jeans are. And the more distressed the denim is, the more casual it is. I kind of compare it to sweatpants, and here’s what I mean. Imagine a scale that goes from sweatpants, all the way up to dark denim. I’m guessing you wouldn’t wear oxfords and a necktie with a pair of sweatpants. So, because it’s a lot harder to dress up something that casual, the question is, at what point along the scale IS that possible? Here’s my take on it.
In terms of blue jeans, consider that the lighter the color is, the closer to sweatpants they are on the scale. Same goes for distressing. The more rips and wiskering, the more casual they are. As we move up the scale towards solid darker blue, the dressier we get and more appropriate we get in terms of dressing them up. Especially once you hit 40 and beyond.
Now, I do want to acknowledge that denim comes in all the colors of the rainbow and there’s more options of dressing up those colors than I have time for in this video, obviously. I also want to acknowledge that lighter wash blue jeans can look pretty cool with boots if you’re going for a rugged look. However, for this video, we’re gonna stick with blue jeans for some inspiration leaning more towards smart casual. And with that, let’s keep it moving.
Once again, there’s a lot of options out there so I’m gonna cover a few of my own personal favorites. Oxfords, Derby’s, Chelsea boots and loafers. These brown oxfords are my go-to when it comes to dressing up jeans. They’re the Allen Edmunds Strand model, and I’ve had ‘em for about 6-7 years now. They might need a polish, but they’re still beautiful, comfortable and incredibly versatile. You could wear these with a suit, all the way down to jeans.
Same thing goes for these wingtip Derby’s from Ace Marks. They’re very similar to the Allen Edmunds, but because they’re a Derby, they’re even more casual. Real quick though, just to cover the difference between an Oxford and a Derby. The Oxford uses closed laces, meaning the flaps with the lace holes are sewn closed at the bottom. The Derby has the flaps completely open at the bottom and you can stick your finger in there. That small difference will always make the Derby more casual than the Oxford.
Denim fit is critical
A couple other things to consider here; The fit of your jeans, and the color of your shoes. You want your jeans to fit well without being too loose and baggy, and also not too long. You really want to avoid excess break and puddling down at your shoes because it looks very sloppy. And it looks like your pants are trying to swallow up your shoes. I mean, if you made the effort to wear nice shoes, we should be able to see ‘em, right?
The other thing to consider is the color. Brown is always gonna be very versatile, especially with denim because they’re complimenting colors on the color wheel. I’ve talked about the color wheel before, but if you want to go check out the interactive color wheel on Canva, I’ll link it here. I would suggest that you avoid wearing black dress shoes all together with jeans. Black is just way too formal to wear with jeans, even with a Derby. Boots are another story because boots are inherently more casual anyway, but if you’re going with a standard shoe, your best bet is gonna be medium brown.
Next, let’s talk about your upper half starting with shirts. Now, since the goal is to “dress up” your jeans, we’ll talk about dress shirts that are tucked in. Now yes, you can look good with your shirt untucked, but for the sake of this video, we’re gonna go ahead and tuck it in. And we’re also going to make sure it’s ironed. One of the things that have always bugged me about dress shirts, is when I have the top two buttons open, the placket flops over and looks a little sloppy.
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So with dress shirts, I might suggest choosing something that has some type of pattern to it. Plain white or blue will always look nice, but a small stripe or a check pattern that reads slightly more casual fits in a little better. Especially with the more casual look and feel of jeans. It doesn’t have to be anything too crazy, but a smaller, tighter pattern does tend to read a little more dressy than a larger pattern or print. If the weather gets a little cold, layering with a sweater is another great option. It’ll keep you warm and also add some additional depth and texture.
Sweaters & Sports Jackets
If the weather is cold where you are, you might want to consider another top layer in the form of a sports jacket. This is where it gets fun because you can mess with pattern a little bit more. Instead of a solid blue or solid gray sports jacket that would still look great, go for something with a little more pattern to avoid looking too plain. Remember, you’re wearing jeans, not suit trousers so use that to your advantage. The perfect time to incorporate a jacket like this is when you’re wearing jeans because it just makes so much sense. And you’ll look amazing.
Lastly, on my list of how you can dress up your jeans is with accessories. Now, because we’re tucking in our shirt, we probably need a belt. The same basic rules apply with suiting. Closely match your belt to your shoes. That means if you’re wearing brown shoes, wear a brown belt not black. Wear a watch with a leather strap or a steel bracelet, not a NATO strap. NATO straps are great when you’re going more casual, but when you want to dress things up, swap it out for something a little nicer.
Socks & pocket squares
With socks, match ‘em to the general color of your pants, and avoid crazy patterns and cartoon designs. I’m okay with some pattern, but the wacky socks are a little tacky in my opinion. If you’re wearing a jacket, wear a pocket square that coordinates color with something else you’re wearing. If you need help with that, refer back to the color wheel to make sure it’s a complimenting or triadic color.