A lot can be said about you simply from how good or terrible you dress and look. It becomes challenging if you have friends and colleagues who, in your opinion, do not look good.
For one or more reasons, you may be tempted to tell them what you think and feel about how they look. But, how do you politely tell someone they look bad?
Pointing out inappropriate clothing to someone should always be done in person and in private. In a professional context, it is easiest to refer to the generally prevailing style of dress. In a personal context, you can be blunt in your criticism as long as you remain polite.
Actionable Advice To Tell Someone They Look Bad
Your first instinct should be to define the setting.
If you are concerned about someone’s appearance and look, learn to differentiate between official and unofficial settings.
In most cases, both may involve hurting the person’s feelings – depending on your approach.
For official looks, there is often a pre-determined and set dress code or appearance expectations. As such, regardless, you are still entitled to offer concern for the general good.
On the other hand, unofficial settings do not need your opinion. The other person is often at will to dress and look as they please.
In both situations, if you are uncomfortable about how the person looks and would like to speak up, it is important to practice politeness. Any other way tends to impair relationships, friendships, and the person’s self-esteem.
The Feedback Fallacy implies that focusing on individuals’ shortcomings doesn’t allow learning; it only impairs it.  How then do you give constructive feedback to your work colleagues and friends?
If It’s Non-Work-Related
Below are tactical ways to politely tell someone they look bad:
1. Consider the Sly Approach
This is a practical and actionable solution to get someone to lose their general appearance.
Surprise the person with new attire that you believe would improve their aesthetics.
However, this would require you to be close to this person to minimize the chances of coming off as weird and insensitive.
If you are concerned about their grooming, surprise the individual with a paid spa treatment or haircut.
Depending on your approach, the individual should pick up on the non-verbal cue about your thoughts on their appearance.
2. Offer Your Assistance
If you genuinely believe the person is struggling with presentation and looking good, the prudent thing to do would be to offer your help.
Ask them for permission to access their dressing room so that you can help them come up with a good look.
3. Be Bold
Ensure you and the person have a strong bond that wouldn’t be easily jeopardized by every sensitive comment.
Tell them your frank opinion and offer advice if they require any.
Do not be rude or insensitive if you want to pass across your opinion and not condemnation.
It is important to remember you are not telling the person your opinion not to be mean or catty. Think of it as a casual conversation where you point out minor errors.
If It’s Work-Related
Whether you like it or not, your appearance affects your success at work.  As such, it is understandable if you want to tell someone they look bad.
If you are not proud or comfortable about your co-worker’s look or appearance, it is important to remind yourself that what you do about it is for your workplace’s productivity.
In official settings, looking good is essentially dressing professionally and ensuring personal grooming.
Dressing professionally and looking good go hand in hand and serves the interest of your company.  It also helps you feel a part of the team.
Below are ways to politely tell your fellow employee that they look bad:
1. Ensure there is an outlined clear dress code
Having a clear outlined dress code serves as evidence to refer to if someone is dressing unprofessionally and looking bad almost intentionally.
Clearly and politely remind the person to stick to the dressing code.
2. Define Dress-Down Fridays
Make sure everyone understands what is appropriate on dress-down Fridays and that their appearance does not interfere with anyone’s comfort. 
3. Talk to them Politely
Talking helps a lot with sharing your opinion. However, the challenge is not to talk insensitively.
Looks and appearances are not things you should email someone about.
Talk to them in person and explain the situation with their look without sounding vague.
4. Be Positive
The goal is not to make the employee feel like you are picking on them.
Therefore, ensure you emphasize all the positive points.
5. Act Quickly
The more comfortable you get with someone’s unprofessional and unappealing appearance, the more they get comfortable pulling the same look.
Take the initiative and address the problem sooner.
6. Talk Privately
This applies to your friends or co-workers. Chances are you are not the only person who noticed they look bad.
There is no point in bringing it up in front of everyone else.
Talk to the person privately, which shows that you respect their feelings equally.
7. Discuss Solutions
Discuss simple solutions that can help the problem instantly.
For example, if the person is sagging down trousers, a belt would be appropriate to help keep it up.
8. Don’t get too Personal
Remember you have a problem with how they look in terms of presentation. Ensure you only discuss noticeable grooming and dressing.
Do not talk about whether their dressing makes them look unattractive or fat.
Is someone close to you not looking their best, and you are generally concerned? Here is what you ought to tell them.
Example Phrases To Politely Tell Someone They Don’t Look Good
Below are some things to tell someone if you feel they are crossing boundaries or struggling too hard or little to look good.
“I will understand if you say you are feeling confident about how you look right now. But if you don’t, then I may be able to help you come up with something more visually appealing and evoking the right confidence.”
“I have brought you a new pair of jeans (or makeup, jacket, t-shirts) that you can try on. It looks way better than the others. You can keep the others for a different occasion or use.”
“How do you feel about going shopping and choosing a new look for you and me?”
“I admire your confidence in pulling this look and these clothes. However, it is my humble opinion that they are not bringing out all your beautiful features.”
“Is there something bothering you that you want to talk about that you believe is affecting how you take care of yourself?”
“You have made considerable effort in this area (where you notice effort). However, I can’t imagine how much better you would look if you worked on this (where you believe they don’t look good).”
“You look great, but what if we got you the same attire or look but in a different color or style to try out?”
“I appreciate your effort in dressing up to come to work, which means a lot. However, I believe that your overall appearance does not fit with the office’s dress code. Would it be kind of you to tweak it a little bit?”
“You are about to do something memorable for years to come. I am just letting you know in case you may want to improve on something to ensure you are proud of this moment.”
Refer to your concern once they are interested in your thoughts.
“Do you feel confident in how you look now? If not, we can always do something about it.”
Under What Circumstances Would You Be Obliged To Speak Up?
Different situations and scenarios call for immediate attention and action.
Here are situations where you would have to politely tell someone they look bad.
The workplace demands a professional, almost a strict dress code and general appearance.
If you or either of your co-workers does not feel comfortable about another employee’s look, you are obliged to speak, especially if they are in clear violation of any set code of conduct.
If you notice a friend or acquaintance has underdone or overdone an aspect of grooming, it is advisable to notice them and share your opinion without seeming to force them to comply.
For example, if your friend has put excess makeup on their face, looks out of order, or smells strange, point it out immediately.
In addition, if the person’s clothing is either torn or dirty on sensitive parts, talk to them about it.
Doing so is especially crucial if it appears they are unaware or if there is an important event.
Sometimes, it is a simple act of care.
Unfortunately, most people are of the general opinion that you should never impose your opinion, especially if it involves someone’s look.
It may tend to sound like you are questioning their judgment and choices.
Telling someone that they look bad is not pleasant. In most cases, it may involve evoking distrust and negative emotions.
Regardless, your approach should matter in passing across the message politely.
Most importantly, ensure you develop some nice rapport which should set the ground comfortably.