Men’s Over 40 Fashion: How to Wear Dark Denim

by | August 2019

Dark denim should be a staple in every man’s wardrobe. It is versatile and easy to dress up or down. Additionally, every body type looks great in dark denim.

As with all fashion trends, what was once old is now new. We can thank Levi Straus for the introduction to indigo wash denim. Originally intended as rugged work attire, denim became a symbol of disobedience as Levis Straus secured contracts to outfit inmates. Perhaps it is this association with correctional facilities that earned denim its bad boy reputation. Denim is now a fashion statement, and we can thank Dussault Apparel, Inc. for creating a pair of hand-painted denim jeans adorned with 18-carat gold, diamond and ruby accents, and a hefty price tag of $250,000.

Guys, here is the deal. Improperly fitting jeans look frumpy regardless of the price tag. Dropping a cool quarter-mil on pair jeans does not excuse one from knowing the basics about denim. Wearing dark denim in particular starts with the correct fit. It does not matter how you dress up or dress down your outfit, a bad fit creates a bad first impression.

FIT: For a more polished appearance, jeans should be long enough to have a slight-half or full break, with slim-fit jeans falling to the ankle. Avoid rolling, cuffing, or allowing slack around the ankle. You should be able to pinch a minimum of one, but no more than one and a half, inches of fabric on each side of your thigh.

WAIST & SEAT: Midrise jeans are typically the most flattering look and should fit perfectly around the waist without the need for a belt. The waist should sit anywhere from mid- to upper hip. The seat should not sag or feel tight; instead, jeans should lightly (not tightly) hug your glutes.

STYLE/CUT: When selecting your style, you want to think “fitted;” not skin tight and not baggy. Depending on body type, slim fit jeans are typically the most attractive fit with straight leg jeans following closely behind. Know your cuts:

Skinny jeans are the tightest, snuggest fit available. Think spandex.
Slim fit jeans are snug around the legs, but not skintight. They slightly hug the thighs, knees, and calves while tapering from knee to ankle.
Straight leg jeans are narrow below the knee but not skintight. The leg opening is slightly wider than skinny jeans.
Boot Cut jeans flare below the knee.
Relaxed fit jeans, also called “loose fit jeans,” are baggier in the thigh and throughout the leg.

Men with Larger Builds: If you are a man with a larger build, a balanced approach is best. Avoid anything with a tapered leg. If you can pinch more than one to one and a half inches of fabric on either side of your thighs, try a smaller size, consider a slimmer cut, or select a different brand.

LET’S GET DRESSED

Now that we are wearing the best fitting jeans possible, we can start making you outfit situation appropriate! Dark denim is an essential wardrobe piece because it can be dressed up or dressed down from neat/smart casual to date night to simply hanging out.

SHOES: When assessing situation-appropriate attire, always start with your shoes. Believe it or not, shoes will not only make or break the outfit, but it is a statement piece that creates the first impression. Don’t believe me – try it for yourself. Throw on a nice pair of shoes and pay attention to where people’s eyes naturally drift. More often than not, they go directly to your shoes.

You can pull off dark denim with most casual dress shoes. Consider pairing your dark denim jeans with a pair of Allen Edmonds “Strand” Cap Toe Oxfords for dressier occasions like date night. Less formal dress shoes, in general, take the look of your jeans from casual to sophisticated. For a more laid-back look, pair your dark denim with Italian leather or suede sneakers. You can even go ultra-casual with a pair of white tennis fashion sneakers.

SHIRTS: Dark denim can be used to tone down bright colors and matched in many different ways. From t-shirts and hoodies, fitted sweaters, and long-sleeve dress shirts, to dress shirts accompanied by a jacket and tie – it all works. One well-debated fashion rule is pairing a black or a navy blue shirt with dark denim. Dark colors either go well together or they clash. Your shirt should complement your jeans – not compete with them. When in doubt, grab a different shirt.

Try pairing a pair of dark denim jeans, brogues, and a white dress shirt. It is a simple but fantastic look! A small-patterned, soft-hued button-down shirt always goes well with dark denim. In the latter scenario, your shoes will dictate the degree of formality.

JACKETS & TIES: Dark denim looks great with a sports jacket, blazer, a leather jacket, and even a denim jacket providing it is of a much lighter hue. Try pairing a sports jacket with a small-print short sleeve shirt and casual dress shoes. Kick it up a degree and add a tie. For a more relaxed look, match a lighter denim jacket with a soft Henley shirt, and a pair of fashion tennis sneakers.

ACCESSORIES: For maximum impact, keep it simple. Add a belt and watch to your ensemble and you are off! If you are feeling edgy, break the rules a little. Pair your favorite French cuffs with casual and very subtle cuff links.

MATCHING BELTS, SHOES, AND WATCHES: This topic will continue to plague generations to come. Leather shoes and belts should be in the same color family; however, they do not need to be the exact tones. The more contrast between the two, the less stylish you look. In other words, tan and oxblood are not the same as brown. On that note, suede is suede. Finally, canvas belt straps should complement the outfit, not draw attention from your outfit.

Always match your metals, with the exception of your wedding ring. Everyone gets a pass on this one. The metal of your belt buckle should match the metal of your other accessories, including your watch. This rule is easy to bend and it should not get in the way of wearing sentimental pieces like your great grandfather’s watch. The big ticket here is matching your belt and shoes.

There is no doubt that dark denim will upgrade your wardrobe. Just about everything goes well with dark denim. The key is the proper fit, situational awareness, and shoes. Always start with your shoes and allow the outfit to come together from there. Keep the basics in mind:

  1. Pinch an Inch: A minimum of 1 inch of fabric, but no more than one and a half inches, on either side of the thigh.
  2. Say No to Seat Sag: The seat should not sag.
  3. Cut: Know your style/cut.
  4. Mid-rise: Fit at the waist without a belt.
  5. Bottoms up: Plan your outfit around your shoes.
  6. Break: They should have a slight or full break.
  7. Situational Awareness: Be aware of the situation (smart casual setting vs. hanging out watching the game).
  8. Keep it Simple: Minimally accessorize with a belt and a watch.
  9. Be brave.

You may need to step outside of your comfort zone and ditch the cargos and acid wash jeans we grew to love in the ’80s and ‘90s. Stick to the essential rules and enjoy the wardrobe flexibility dark denim provides. Most of all, have fun.