How to Experiment With Your Look Without Hating the Result

Caught between wanting a change but not wanting to end up accidentally looking ridiculous? Try this!


So you want to change things up, huh? I don’t blame you. I often find myself wearing the same old clothes until my girlfriend inevitably complains about my T-shirts turning into caveman-style torso wraps. I also haven’t had a considerable haircut since some time back in 2015, which is just plain sad.

But as you know, change is scary. What happens if I decide to cut my hair and end up with something that I totally hate? I’d have to spend the whole year wearing hats and growing my hair back out. Or what if I buy a bunch of clothes, then realize I look ridiculous? What a waste!

According to our various experts, there are some simple ways to change up your look without doing anything too drastic — we’ve listed their advice below, starting with what might be the most important part of all: Your mind. Men can be, well, pretty terrible when it comes to supporting each other, and more often than not it’s the thought of being roasted by friends and colleagues that makes people reluctant to drastically update their look. So before you start messing with your appearance, it’s important to get in the right mindset and feel confident about what you’re doing. 

Let’s get to it…

Deborah Heiser, applied development psychologist with a specialty in aging, and founder of The Mentor Project: Some people embrace change in their environment and their wardrobe, while others enjoy routine. [Whichever kind of person you are] can be due to:

1) Our Identity: Finding a look that matches how we see ourselves — trendy, preppy, corporate, conservative or perhaps laid back — is one way we express our identity. Changing our hair or wardrobe fits within this. But to see change and feel like we don’t have control over it — e.g., loss of hair or graying — can initially be distressing.

2) Our Personal Homeostasis: We all have our arousal ‘base’ that we feel most comfortable with. Some feel bored if they aren’t out socializing or changing their wardrobe, whereas others feel overstimulated if they’re out at a party, and they need to go home and rest afterwards — wardrobe and hairstyle changes also aren’t things they feel the need to change as often. This is based on our internal arousal level: Some people change their wardrobe every season, and they update their facial hair and get haircuts regularly. Others are comfortable in the same clothes season after season and don’t change their facial hair or hairstyle often.

To gather the courage to change, try to imagine your new look within your identity and within your comfort zone. By imagining the new look and visualizing yourself in everyday settings with that look, it will help prepare you for the next step. For some, it’s also helpful to talk with someone about the change — many girlfriends welcome a new look, and many friends may also be very supportive.

Zain Nawaz, Dollar Shave Club’s resident beard expert: If you want to experiment with your beard, try doing it on a Friday after work. This way, you can remain in isolation and cry without being seen by your friends, and hopefully by Monday, some of the chaos you’ve created will be covered up. Secondly, it’s always good to Google beard styles and then emulate looks that you like. Even having someone assist you can be a good move, since this is new territory.

Rayne Parvis, stylist: To experiment with your look, try new colors and prints in a style that you like. For example, if you know you feel great in a white T-shirt and blue jeans, try a blue T-shirt and gray jeans in a similar style that you already like (most stores have many colors in the same styles). Then, to add an element of style, try a sports coat with a fun pocket square. If you feel too fancy in a sports coat or blazer, try a bomber jacket in a fresh color. 

To sum it up, pick something you already love to wear and see if you can reinvent it in different colors and prints. Then add that third piece of something interesting — either jewelry (like a leather bracelet or a watch) or interesting jacket.

Asia J, barber: If you’re thinking about changing something, the best thing you should do is go to your barber — even for a consultation, which is sometimes free — because they know what looks good on you.

Vanessa Rodriguez, hairdresser at Simbiotica Hair House: Look at pictures of the styles you like, and take them to your hairstylist. That way, your hairstylist can let you know what will look good on you and what would work for your hair type. The good thing with guys is that their hair grows quickly. So I usually show them pictures, and we both agree on what to do. In my experience, I’d say that guys don’t like their hair too short, so I mostly cut a little at a time until we’re both happy.