How To Compliment Someone’s Clothes Without Sounding Weird

I recently got asked “how do you compliment someone’s fashion without sounding weird” and I honestly think it’s a great question. First of all, it’s true that not all compliments are welcome or appropriate. Secondly, compliments are an excellent ice-breaker for learning how to network yet if not done right can make you seem fake. Thirdly, learning the art of complimenting can help you grow your own confidence.

#1 Be Sincere

When you give a compliment, it has to be something you actually mean and believe. Don’t tell someone how much you like their hat when you think it looks ridiculous. Most people can sense insincerity and it will backfire. They may even feel offended as though you were making fun of them. So only give outfit compliments for outfits you really like.

#2 Be Specific

Generic compliments are fine, but easily forgotten. They don’t really make an impact. They might solicit a quick “thank you” but don’t allow for follow-up conversations or a real emotional effect. If you’re specific, you’ll not only be memorable, but you might end up learning something really cool about the person you’re talking to. So, one specific way how to compliment someone’s clothes is to tell them what you like about that particular item. Is it unique in some way? Mention how.

#3 Ask Questions

Another way to compliment someone is by mentioning what you like then asking a question about it. Maybe it has a special history or some kind of sentimental value to the person. Maybe it’s from their favorite designer or fashion era. Or maybe it was a huge bargain that they’re very proud they got. Asking about whether an interesting piece of clothing or jewelry has a particular story is a wonderful way to get a conversation going and to show your curiosity. Just be careful not to ask inappropriate questions!

#4 Pick The Right Moment

How do you compliment someone’s clothes without being awkward? Well, all of the above won’t matter unless you pick the right moment. If someone seems quite reserved, complimenting them in front of a group of other people might be embarrassing for them. One-on-one might be better. Also, if it’s in the middle of a serious conversation or when there’s some kind of event that has everyone’s attention, it might come off as a bit disruptive. Picking the right moment means you need to be aware of the situation as well as the person you want to compliment. Want to learn other important social hacks? Click here.

#5 Learn How To Receive Compliments

Giving compliments and receiving them are two sides of the same coin. And learning how to receive them can help you figure out which feel appropriate and which don’t. So ask yourself: what does it mean when someone compliments your clothes? Looking at the situation, you might find that it could be a conversation starter, sincere admiration, or maybe a sign of attraction. Understanding the meaning can help you respond to and receive the compliment in the most graceful way possible.


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Anna Bey is an educator in the elegant feminine empowerment space and the founder of an online finishing school for women. She can confidently call herself a pioneer in this genre because she was the first to be sharing content in this niche since 2012.

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Anna Bey is an expert on Modern Elegance™, upscale transformations, and leveling up, with over 150 million channel views. Since 2012, she has taught women how to develop a more refined personal presence and lifestyle inside the Anna Bey Academy, where she hosts her various classes and courses. Her publication features include The Times UK, Newsweek, New York Post, Cosmopolitan, and many more.

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