Here’s How to Dress Younger with Classic Style

Contrary to what people like to think, dressing according to a classic style doesn’t mean looking like an old man. In fact, you can actually dress younger and appear more youthful by utilizing many classic style hallmarks.

1. Play with Formality

Many people think classic style means only wearing a suit. In reality, classic style comes in all formalities; and casualness will usually be associated with youth. So, while a charcoal three-piece suit can come across as older, there’s plenty of creative options within classic style that actually come across as younger options.

Harrington jackets, turtlenecks, leather jackets, and dark denim are all classically youthful and could be seen worn by plenty of young and rebellious figures within pop culture. No one ever accused Steve McQueen of looking old after all; plus, these items have far more versatility than something like a T-shirt or a hoodie.

For example, a leather jacket or a field coat can work equally well in a business casual or casual setting. It just depends on the accessories and other items around it.

It’s also worth noting that playing with accessories and jewelry can create a more casual edge—adding a simple necklace, ring, or watch can give your outfit a more casual or playful nature. Just make sure not to overdo it.

2. Sportiness

Did you know that many classic style essentials were originally seen as sporting wear? This is especially true of examples seen in the 1920s and 30s, when classic style became more youth-oriented, featuring styling conventions influenced by college students, varsity athletes, and gentlemen of leisure.

Polo shirts, motorcycle jackets, sports jackets, etc., were all once default uniforms for players and audiences of tennis, golf, and other sports. Even if they’re not seen in modern athletics anymore, wearing them still conveys a sense of youthful athletic sportiness similar to athleisure but with a classic touch.

These pieces, however, will be far more versatile and elegant, and with business casual being the most formal dress code many wear today, they can be used in a great many situations—whether it’s for work, on the weekends, or even for a special event. Athleisure, on the other hand, is almost always going to fall in the casual spectrum, no matter how much their marketing might argue otherwise. Not to mention, the structured, more tailored look will be more flattering than most athleisure, even if you don’t personally play sports.

3. Layering

Creativity can take an otherwise bland outfit and inject it with some of that youthful spirit. Instead of always just defaulting to the most typical option, switch it up by creating contrast, finding unexpected pairings, and blending formalities. This could mean including a more casual sweater with the right suit, trying to use Winchester collars in more relaxed outfits, or including dark wash denim with tailoring.

What matters is that you’re experimenting to find the combos that speak to you personally. Not every attempt will be a hit, but the ones that are will have a fun and playful effect, which will give you massive style points. It indicates awareness of how to build an outfit correctly and that you’re breaking the rules for your style instead. Rules are made to be broken, after all.

Even if you personally might not wear blue jeans with a tuxedo jacket. And you can learn more from our guide to layering.

4. Color

Navy, gray, and brown are classic but can come across as older depending on how they are styled. If you’re really looking to give your outfit a youthful edge, look to include more vibrance instead. Olive green, burgundy, pink, purple, and orange can be much more playful and give life to an otherwise dull outfit.

You don’t have to go all out with an orange jacket or purple sweater, either. In fact, it’s probably more beneficial to incorporate pops of color in your accessories first. That being said, if you want to stick to basic colors, try tonal looks. We’ve seen these all over Hollywood and fashion houses as a way to give outfits a modern edge. Emulating them will create a similar effect for you as well.

However, the monochromatic trend, which is largely played out, should be avoided. Preston teaches the difference between tonal and monochromatic in another guide.

5. Hair

Hair changes affect almost all men at some point in their lives, meaning that thinning hair, balding, or graying is simply a part of life. Often, attempts to overcorrect the issue just draw attention to it. We’re talking here about wet, drippy hair dye and obvious comb-overs.

Finding a haircut that suits the reality of your hair will always look best, and while looking at a trendier hairstyle isn’t inherently a bad choice, many trends are designed for men with full heads of hair that won’t suit all hair types or densities. Instead, it’s better to find a balance between what personally looks good on you and what is currently in.

Don’t default to the assumption that longer hair will mean a youthful look in every scenario. Shorter styles that are suited to your hair realities generally have a more pleasing, youthful effect than longer cuts that just emphasize what isn’t there anymore. This is just one of the many style tips for thinning hair, which we made a guide about previously.

6. Grooming

Everyone loves a good beard or mustache, but there’s a reason they’re considered sophisticated and often associated with older gentlemen. If you’re trying to appear as young as possible, a clean shaven look might be your strongest choice. Not to say you can’t have facial hair; in fact, light stubble or trim facial hair can create a similar effect. Just make sure they’re maintained properly. But having no facial hair at all will usually create the youngest possible appearance.

The stereotype of beards hiding boyish faces exists for a reason. But, if you prefer facial hair, keeping it neat and trim will still convey a sense of youthfulness.

It’s also worth noting that the regular use of a basic moisturizer is beneficial at any age, as many of them are designed to help prevent and reduce wrinkles and other signs of getting older. This process doesn’t have to be very intensive either, as a little bit of consistent effort can go a long way. While starting when you’re younger is the ideal scenario, the second best time to start is now.

7. Fit

Above all else, this is what will impact how you come across in your clothes. Ill-fitting clothing will make anyone look worse. This goes beyond standard fit advice, though. It’s easy to fall into the trap of buying clothes with trendy cuts.

Most trendy clothing is really only cut for one body type and wouldn’t seem age appropriate on someone who isn’t in that mold. Chances are, as you age, you won’t have the same body type as you did when you were younger. Plus, trying to dress like a 16-year-old will only make it more obvious that you’re not 16.

Fit realities also change as you age. In particular, oversized clothing can appear sloppy the older you get, whereas it could be seen as trendy when you are younger. Instead, find a balance between a fit that suits your body type and makes you appear younger.

Even within the context of classic style, there are more versatile, trendy elements that you can consider including in your wardrobe if desired. No trouser break, flat front pants, a lower rise around the waist, tapered legs, and so on are all options in classic style that create a younger effect. Trust us, wanting to appear young isn’t a novel concept.

8. Confidence

Finally, remember how you act is just as important as how you look. You can dress as youthful as possible, but if you don’t look comfortable with yourself, it won’t mean much. Aging is a part of life, and trying too hard to cover it up isn’t worth it. A few gray hairs never hurt anyone; instead, it’s better to embrace who you are and then work to tailor the image that you want around it.

Confidence is timelessly appealing. Don’t let a culture obsessed with youth take that away from you. Classic style can mean many different things; leveraging these principles can help you have a youthful edge in your style without compromising on that classic aesthetic.

Think we left any good advice out? Let us know in the comments.

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