How You Can Dress Cool With Almost No Effort

Dressing well doesn’t have to take much effort — in fact, “casual cool” can be one of the easiest looks to rock. It’s all about knowing your personal style and what works for your body type, and then wearing the hell out of it with an attitude to boot. Dressing cool simply means you look and feel relaxed, casual, and confident. You might need a little help to get started. With the help of these seven tips, you’ll look effortlessly cool in no time.

1. Assess your closet

man getting dressed next to his shirts

Keep tabs on what you have and what you need. |

One of the first and most important steps you can take, besides having expertly tailored clothes, is to make it easy to find your clothes. Go through your closet piece by piece and assess what fits you, and if you feel comfortable wearing each item. Separate your clothes into four piles to expedite this process: keep, give away, tailor, and not-in-season. This gives you both closet space and brain space to think about garments that pair well together.

Nothing says cool and relaxed like being able to reach into your closet and feel confident in whatever you pick out. All of your clothes should go together. For example, you shouldn’t have anything that stands out like a sore thumb, be it the color or an outdated style that doesn’t work for you anymore.

If you need help assessing your closet, enlist a fashionable friend. Your goal is to eliminate what is unnecessary or outdated — think patterned jeans or juvenile graphic tees.

2. Ignore the trends

man in a hat and plaid shirt

Stay true to your personal style. |

Dressing cool is all about knowing what looks good on you. This means that even though you are aware of the trends in menswear, you respectfully reject the ones that don’t work for you. Guys who dress cool always march to the beat of their own drum.

3. Think about your physique

Knowing what clothes work for your body type will help when it comes time to shop |

Knowing what clothes work for your body type will help when it comes time to shop. |

The more fit you are, the better most clothing will fit you. But if you don’t fall into the “super fit” category, there is no need to feel discouraged; it’s just a matter of figuring out what general body shape you fall into and learning how to dress accordingly. Although you may not be able to fake physical fitness, figuring out the right way to dress for your body type will help to minimize problem areas and give you the foundation for the kind of clothing you should be wearing to exude a cool vibe.

4. Find a tailor you love

a tailor next to his garments

Something that almost fits does not fit, so get it tailored. |

Besides assessing your closet, the most important aspect to dressing cool is having clothes that fit you perfectly. A good fit is absolutely nonnegotiable. As a general rule, your shirts shouldn’t puff out at the waist and or be oversized; your pants shouldn’t require a belt; and your jeans should be slim-fitting and not too long. Find a tailor who knows the ins and outs of a well-fitted garment. Or try a local dry cleaner that does alternations.

5. Find a style icon

man relaxing in a sweater

Find inspiration from someone else. |

If you still haven’t hit on a look that is distinctly yours, find some style inspiration. Are you more a classic Brad Pitt or a rebellious Justin Theroux kind of guy? Either way, by taking cues from their effortlessly cool style, you’re sure to bag yourself a Jen Aniston lookalike. Study up, gentlemen.

6. Go shopping

clothes shopping

Shop for new staple pieces. |

After doing your style research and assessing your wardrobe, it’s time to go shopping. Enlist your same stylish friend to lend you a helping hand, and look for pieces that match your stylist aesthetic and fit your body type. This may involve multiple hours in dressing rooms. Be discerning of what truly does and does not work for you.

7. Rock your cool look

man in sunglasses looking cool

A pair of shades will always help. | Pablo Cuadra/Getty Images

Put it all together. Just remember: Dressing cool means looking like your style is effortless and natural. Make sure you don’t look overdone. Keep your accessories well-balanced. And never leave home without an iconic pair of shades.