“Help! My Friends & Family Don’t Understand My Style!” – Tips for Self Confidence

Being a classic style enthusiast, regardless of your age group–teenage, young adult, middle-age, or beyond–comes with challenges when your friends, family, or peers just don’t seem to understand your style. Today, we’ll discuss how you can continue to express yourself via classic style and do so confidently, even when others seem to be unsupportive.

The Classic Style Enthusiast’s Challenge

One of the most frequent social media comments or emails that we get from our readers and viewers (especially our younger viewers) often goes something like this: “I want to dress up more, wear suits, or dress differently than the people around me–but my friends and family don’t understand or support my style choices. What can I do?”

I can definitely sympathize with men who feel this way. Personally speaking, I developed an interest in classic menswear in my early teens, but my parents were concerned that if I dressed too differently from my peers, combined with my general bookishness and a physical disability, that it might lead to social awkwardness or even bullying.

Fortunately, however, my friends and general peers were largely supportive of my experimentation as I got more into classic style, so I didn’t have to worry too much. But I do realize that this won’t be the case for everyone. And this back and forth with my parents through my teen years was a bit of a sore spot for a while, but thankfully they’ve now embraced the way that I dress; after all, it’s led to a career!

Meanwhile, in Raphael’s case, his family was never really all that interested in clothes, and dressing was really more a matter of function and cost than of style. So for both of us, as we developed this interest in classic style, it was because it resonated with us on a personal level, not because of any outside pressure from others to get into it. In fact, it might have been just the opposite.

Techniques To Deal with People Criticizing Your Style

So, if you’re experiencing pushback from friends, family, or peers about getting into classic style (whether you’re young or at any other age), here are six techniques we’ve come up with to work through this.

1. Focus on things you can control.

In the case of many of our young readers and viewers, they may not have total control over the way that they dress, because they are financially dependent on their parents or caregivers. Thus, the clothes that are bought for them may be decided for them. There may also be other financial dependencies involved, or it could just be that their parents are particularly strict and try to control the way that they dress.

These situations aren’t easy to change, so the best thing to do here is to work with what is firmly in your control. For example, you can be persistent in asking why it is that you have to dress a certain way. Your goal here should be to negotiate and ultimately compromise with whoever is in control. It’s important to note here that you should be crafting arguments that are ultimately about you and not about others.

So, for example, rather than saying, “Everybody else gets to wear what they want,” you should just say, “I’d like to dress this way because it makes me feel more comfortable with myself.”A related point here is to be resourceful with what you do have, using your free time to build your menswear knowledge or to go to vintage or secondhand stores if you have the ability.

2. Consider this journey as a rite of passage.

This one may sound like cold comfort for our younger viewers, but horrifying your parents with your clothing choices is something that almost every young person has to do. In this case, though, it might just be that you’re horrifying them with slightly more conservative choices! For example, in Raphael’s generation, the “grunge” look was definitely vilified by parents. For another, Raphael’s father once asked his father-in-law why he wanted to “look like a girl” with the long hair that he sported in the ’60s.

But going through this bit of struggle can actually be an important part of becoming more of an adult and asserting your independence. Two things are occurring here; the first is individuation, or forming your own independent identity. The second is detachment, or the gradual separation between yourself and those that have power or influence over your life.

Of course, even if you’re not currently a teenager, if you’re just getting into the world of classic menswear, it might not be the case that all of your peers are going to immediately embrace it. So, the lessons in this post aren’t just for young people. You can also take a bit of comfort in the fact that eventually, people will probably stop picking on your style once they see that it is in fact a genuine expression of who you are and that it’s not going to stop anytime soon.

3. Most of the negativity directed at you is really about them.

On a subconscious level, some people may interpret your style choices as an attack on their choices. In other words, they might feel threatened that other people have the courage to dress differently from the mainstream when they themselves don’t. So, because you’re not wearing what they’re wearing, they may interpret this as a rejection of their style rather than an embrace of your own personal style.

The fact is that your style choices probably have almost nothing to do with them, and are instead centered entirely around your own self. So the more that you can internalize that this might be about the insecurities of other people, so much the better.

Alternatively here though, and as it was the case for me, it might also be that your parents’ or friends’ concern is ultimately coming from a place of care, wanting to shield you from criticism or ridicule. And while this situation is ultimately well-meaning, do try to push back a little bit and assert some of that independence by making your own style choices. After all, it’s not as if you’re rebelling here by doing anything dangerous or harmful to yourself or others!

You could try incorporating more of these changes gradually over time, and see what kind of feedback you get. Remember that it may sometimes be about negotiation.

4. Build up your defenses to better rebuff criticism.

Our next tip here is building up your own defenses so that you can easily and comfortably deflect criticism about your style. In times where you’re alone and in a good mental headspace, try practicing your responses to some of the taunting you might receive from other people, like: “Why are you wearing that? Why are you so dressed up? Going to a wedding we didn’t know about?” or “What’s the occasion?”

You have a number of different response options here. If you feel that you can get away with being a little snarky, your first choice is to simply parry these questions back at the other person. So you could ask them, “Why are you dressed that way?” Of course, this might not be the most gentlemanly option, so there are a few others at your disposal. You could try injecting a bit of wit into the exchange, such as by saying “I’m dressed this way because it’s Tuesday” or “I knew I was going to be seeing you, so I wanted to look my best.”

And perhaps the safest choice of all is simply to answer honestly. You can simply say, “I’m dressed this way because it’s what I like to wear.” Remember that if you act sheepish or embarrassed in this situation, some people might see this as a weakness that they can exploit in you. They might be seeking to make you question yourself, and therefore to be able to feel power over you. So, the best way to defuse this situation is by not giving the other individual any conversational power over you, and answering in a way that allows you to retain that power. 

A lesson from Mean Girls

While not totally within our wheelhouse, a great example of this phenomenon comes from the 2004 film, Mean Girls. One character cuts holes in another character’s shirt in an effort to embarrass her, but then she simply wears it proudly, defusing the whole situation and maintaining her own power.

So, raise your head up high, don’t apologize, don’t rationalize, and be proud. After all, you have nothing to apologize for in this circumstance. On that note though, there are situations where all of us make errors and in those situations, and a true gentleman knows how to apologize.

5. Learn to gracefully accept a compliment.

Even though the majority of this post has focused on other people giving you grief for the way you’re dressing, you might also encounter people giving you genuine compliments, and this might make you feel a bit embarrassed if you’re just starting out on your style journey. But of course, compliments are a good thing, so it pays to know how to be gracious when you receive them, as befits a gentleman. 

Of course, some people might not be genuine with a compliment and instead approach it from a place of sarcasm. If you find yourself on the receiving end of this, however, simply treat the compliment as though it were genuine, and this will more likely than not disarm the conversation.

6. Don’t let other people change you.

Finally here, when all is said and done, don’t let other people deter you from who you truly are and want to make yourself into. It may well be that you’re at a point in your life right now where, for any number of reasons, you simply can’t dress the way you actually want to. But don’t let this be the thing that kills your passion!

Keep consuming content, reading, and researching to build your wealth of menswear knowledge. Learn about things like brands, production techniques, and what quality means for your style. Create lists with the clothes you want, where to shop for them, and how much you think you might need to spend. Then, keep working toward your independence, and you will get there one day.

Or, for more concrete inspiration, you could also turn to other men around the web who have definitely embraced their own style. For someone more in our wheelhouse, you could look at Dandy Wellington, or you could also look at the Regency Gent, a man in his 20s who wears nothing but regency attire every day.

Conclusion

Style is a representation of personal identity, so you shouldn’t be embarrassed if your style is making a strong statement, because this just means that you’re secure in your own identity. So long as you can back this up with class and grace, that’s one more step on the road to becoming a true gentleman.

How do you deal with someone who criticizes your style? Share your gentlemanly response in this situation!

Outfit Rundown

I’m wearing something of a business casual outfit whose central piece is one that I’ve had for quite some time. Just around the time in fact that I really started to get on the road of my own style journey.

This would be my tweed herringbone sport jacket which has tones of black-grey, green and brown. Its faux tortoise shell buttons also provide another subtle detail and element of contrast.

Under this, I’m wearing a light gray sweater vest from Polo Ralph Lauren and a barrel cuff dress shirt with a spread collar and a micro-check pattern of light blue and black on a white ground. These colors harmonize with my sport coat as well as my accessories.

These accessories would include a light blue linen pocket square that features a bit of white detailing, a boutonniere in blue and white and a bow tie in a jacquard woven silk with a diamond motif. The bow tie is in battleship gray and its accents are in blue, cream and black.

Grounding the outfit today are my trousers which are plain black as are my socks and my shoes which are plain-toed single monks with a silver buckle.