How to Compliment
Someone's Clothing

It’s true that one of the first things we notice about a person is how they are dressed. And first impressions are in large part formed by what a person is wearing.

We all want to fit in while being ourselves. What we wear offers an opportunity to choose how we mark our individuality. You may even dress according to how you describe yourself:

Casual and sporty
Savvy Professional
Cool and confident
Free-Spirited
Romantic

When you spend a good bit of time dressing for a certain occasion – or any occasion – you probably enjoy it when someone shows appreciation for what you are wearing because they are also showing appreciation for the personal statement you’ve created with your clothing.

But complimenting clothing can sometimes have a catch.

Notice What You’re Noticing

Many people are sensitive about how they look and appear to others. And yet, as inter-dependent creatures, a compliment makes us feel recognized and accepted.

Because what we wear can be a sensitive subject, most of us easily pick up on when a compliment about our clothing is insincere.

Before complimenting someone’s clothing, notice what you’re noticing:

If your motive is to get noticed yourself, the person will pick up on that and the compliment won’t be appreciated.
If your intention is flirtatious, you may be mis-perceived as inappropriate.
If your language is sexually loaded or if you have ulterior motives, you are asking for trouble.

In other words, if you notice you are physically attracted to someone you’ve just met, or work with professionally, it’s best not to show appreciation for what that person is wearing. The subtext of your compliment could be offensive.

On the other side of that, if you meet someone wearing cowboy boots and it brings back memories of the time you spent on your uncle’s ranch, by all means mention it. You have the opportunity to extend a sincere compliment and open a conversation.

A General Compliment

My sister, a middle school teacher, explains the rule she practices that works for anyone, “If you notice and want to compliment a person on what that person is wearing, and the person is in a group, compliment the group.”

“I can’t help but notice how great you look today!”
“A lot of confidence is showing up in how you appear today!”

She also teaches students that singling a person out to give a compliment can create an unfriendly feeling toward that person by others in the group. She further teaches students that if you have something nice to say about what someone is wearing, say it face to face, alone. “Chris, I like your shirt. It complements you well!”

When You Choose to Extend a Compliment

As with all etiquette rules, extending a compliment requires respect. If you have any doubt that what you intend to say will be perceived as insincere or disrespectful, it’s better not to say it.

If you do choose to compliment someone on what he or she is wearing, follow these criteria:

Always give your compliment face to face.
Know your intention. If it is simply to show appreciation for the clothing or accessory someone is wearing, it will probably be well-received.
Don’t linger in the compliment or make a conversation topic out of it. Say it with a sincere smile and move on to another topic.

Another consideration is whether a compliment on something more important than clothing is really in order. Rather than defaulting to a compliment as a desperate conversation opener, choose from a list of topics you keep with you. There is a good chance you may discover the importance of the person instead of his or her outfit.