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Erin Gray (Pronoun: she/her) is a Portland, OR based writer with an affinity for working behind the scenes with companies that offer something unique to their market. When she’s not writing, she likes to roam around mossy hiking trails, wear leather hats, and build stuff. You can find her on instagram @rawhidelaces or email her by clicking on the little envelope below:
There is something undeniably iconic about denim.
The utilitarian appeal of a tough material we can wear like armor to face the day. The way it is made to take a beating and seems to only get better and better the more we wear it.
But when it’s time to bring that sophisticated edge to the party, many opt to ditch the denim for the more lightweight materials that are conventionally associated with dressing up.
The thing is, adding some denim to your more dressed up looks can actually help you ride that elusive line between being too casual or too formal, making you better prepared for any occasion on which you want to look your best.
It comes in especially handy for first impressions (like meeting a significant other’s family) when you want to show some style, but still appear down to earth. So put down the polka dotted pocket square and read on...
We typically associate a tucked in shirt with a neater, cleaner type of look...
However, denim shirts don’t look quite right when tucked in because denim is a heavier material (if you want something that looks like denim but can be completely tucked in, that’s what chambray is for). Leaving it untucked doesn’t mean you can’t still look neat - the key is to make sure the shirt’s length is in proportion with your height.
As a rule of thumb, the lowest part of the tail of an untucked shirt (when buttoned) should fall somewhere between the midpoint and end of your pants fly:
If you absolutely must tuck in your denim shirt, go with the “french tuck” (which you’re probably familiar with if you’ve watched the Queer Eye reboot): tuck in the front of the shirt but not the back. Leaving the back untucked helps the heavier weight fabric not to bunch at the front, giving you a sharper look.
2. Pay attention to the inseam length of your jeans
Nothing says dapper like clothes that fit really really well.
When the inseam of your jeans is too long, they bunch up around your ankles (when done intentionally it’s called “stacking”).
The more streamlined way is to either cuff the leg openings or leave them plain - but to do either one, your jeans must have the proper inseam length.
Here’s a rule of thumb to tell if your jeans need to be hemmed:
Wear your jeans barefoot on a hard floor. If the edge of your pant leg grazes the floor where your heel touches (just barely - not so much that the material folds and stacks) then the length is perfect for wearing them uncuffed. If it’s much longer than that, you’ll need to cuff or they’ll need hemming to avoid appearing baggy when worn plain.
If you’re going to cuff, make sure the bottom edge of the fold is similarly grazing the floor when barefoot. If you have to cuff more than 2 inches of material in order to get there, they need hemming. A cuff over 2 inches high starts to throw your look out of proportion (unless you are well north of 6’ tall).
Getting jeans hemmed to the proper length is without a doubt one of the best investments you’ll ever make. It makes a huge impact for minimal effort, whether you take them to a tailor (average cost $10-15) or learn how to do it yourself with youtube tutorials.
3. Build your look from the ground up
Dapper is in the details, and one of the most important details is footwear.
That’s why one of the easiest ways to make denim less casual is to swap the sneakers for a more sophisticated option such as oxfords, loafers, or (the crowd favorite)... boots!
It’s all about balance. Denim is never going to be super-formal, so the footwear you pair with it shouldn’t be either (leave the shiny black oxfords for your cousin’s wedding). It pairs well with shoes and boots that are on the more casual or even the more daring side of the dress shoe spectrum.
This is a great time to bring out shoes and boots with richer matte textures like suede or pebbled leather. The ones with more memorable details like broguing and monk straps, or unexpected materials like wool.
Instead of black, go with colors that have a bit more variation to them like shades of brown, tan, or oxblood.
As for different styles of footwear, our favorites depend on the season:
In the warmer months, nothing beats a double monk strap loafer with no-show socks.
In the chilly times, we love a chukka boot (a great choice if you’re cuffing) or the sleek silhouette of a suede chelsea boot (best not to cuff).
4. Go dark and you can’t go wrong
Dark denim is a wardrobe staple because it is like a blank canvas. It shows less wear and distress than light denim. Whether it’s a shirt, a jacket, or a pair of jeans, dark denim goes well with nearly every other item in your wardrobe.
When you’re dressing to impress, a darker color helps balance out denim’s otherwise casual vibe.
Don’t be afraid to pair dark jeans with other dark colored items on top. Despite the fact that it’s somewhat taboo, wearing all one shade (dark or light) instead of contrasting sections of color on top and bottom is one effective trick to increase your perceived height. You can still throw in little pops of contrasting color (like bright shoe laces or patterned socks) without losing this effect.
5. Use texture to add contrast
Contrast creates visual interest in any outfit, but most people just contrast with color and leave it at that.
Contrasting textures are just as interesting and denim has its own unique texture that plays very well with others.
One of the best ways to achieve an eye-catching ensemble is by using a variety of textured layering pieces, such as a knit sweater, a suede bomber jacket, or a wool vest on top of your favorite button-up.
The only texture you want to avoid pairing with denim is anything shiny that veers too far off in the formal direction. Opt for accessories that have a matte finish, like a knit tie (or cotton bowtie ).
6. Three words: front pocket wallet
This one isn’t so much about what you wear as it is about what you carry.
Back pockets on jeans are kind of like the outer side pockets on a blazer - it wouldn’t look right if they weren’t there at all, but they’re just not meant to be used like a “real” pocket in the way that front pockets are.
That’s because blazers and jeans have both been designed in their own way to accentuate the longest lines of your body that appeal most to the human eyeball, and anything thicker than paper in your back pocket gets in the way of those wonderful lines.
Carrying a wallet in your front pocket solves this problem, and there are a ton of well designed smaller options on the market that can still fit everything you need to carry and fit nicely into the extra deep front pockets of your Dapper Boi jeans . If your wallet has a footprint similar to a smartphone, it will even fit into our functional front “coin pocket”.
An added bonus of the front pocket wallet (that has nothing to do with how you look) is no longer having to deal with the no-win situation of choosing between sitting on your wallet and doing long term harm to your back, or taking your wallet out whenever you sit down and drastically increasing the chances that it will get lost.
No room in your front pockets? Or maybe you just a prefer your dollar bills to be super crisp and flat? As an alternative (as long as it’s layer season) carry a long slim wallet on the inside pocket of your blazer or jacket. It’s impossible to not feel like a secret agent every time you reach for it.
Did we mention our Casual Knit Blazer has lovely & functional inside pockets? Just sayin’.
What items from your wardrobe do you like to pair the most with Dapper Boi denim? Let us know in the comments!