How to Dress Better

How to Dress Better

Posted by Bill Kavanaugh on Nov 10th 2023

Congratulations! After reading the title of this post, and getting even this far, you’re already demonstrating the first, and perhaps most important requirement of dressing better- wanting to.

This immediately sets you apart from the masses, many who are content to begin each day, pulling on the nearest garment within reach, regardless of fit or appearance.

But you and I are different. We understand that our clothing tells a story to the world. It communicates something about who we are, and what we’re about, without uttering a word. And that’s powerful.

We know that when we dress well, we feel good, .and when we feel good we’re often friendlier, more confident, and open to possibility.

Dressing better doesn’t always mean dressing up- although they’ll be times for that. It’s more about caring, about ourselves and others, a way of celebrating life and giving our best to the world.

There’ll be days we create outfits that knock it out of the park; on others we’ll fall short. But we can always learn something. And as we learn, our understanding and enjoyment of the process will surely grow.

So let’s dive in with suggestions that may help along the way!

1. Take a few minutes to choose what you are going to wear each day. Giving just a little extra thought will help outfits rise above the ordinary and … will make a difference! Try laying the entire outfit out (including shoes) on a flat surface. Play with a few possible combinations. Learn to trust your eye.

2. Google favorite clothing items to gather ideas. For example, if you enjoy corduroy trousers and tweed jackets search that pairing, then hit the images icon. Take note of those that catch your eye. Ask yourself: Why does this arrangement work so well? Is it the colors? Footwear? Accessories? Grab new ideas; put them to use.

3. Like most examples of excellence, much of dressing better is in the details. Because attention to detail is a form of caring. So take time to eliminate wrinkles, check that buttons are buttoned, collars are lying flat, etc. and personal grooming has been attended to.

4. When you put together an outfit that makes you feel like a million bucks, (and you will) take a photo and keep those in a folder for days when you’re in a hurry- or need that ‘killer’ combination.

5. Learn basic rules of dress. There are many worthwhile forums, books and youtube channels on this subject. Here you can get answers to questions such as: Is it appropriate to wear a striped tie with a striped shirt? Or, how do I choose a pocket square? Once understood, you’ll avoid common blunders and feel more confident about choices. And one day you may even break some rules…just because!

6. Spend time in fine clothing stores. Learn what quality garments look and feel like. Cultivate a relationship with sales staff. Ask questions. Buy a little, often.

7. Study style icons, including those from the past. This includes: Fred Astaire Cary Grant and the Prince of Wales (Edward VIII) - and others renowned for their sartorial wizardry. Sure, fashions have changed since then, but the way these masters combined color, pattern and, texture was timeless… and something we can all learn from.

8. Build on a strong foundation. Shoes can make, or break any outfit, so always buy the best you can afford and keep them looking sharp.

9. Remember, Fit is King. No matter how expensive the garment, if it doesn’t fit, it won’t look right and won’t be as flattering as a less expensive garment that does.

10. Above all, be yourself. There is only one you in this world. So wear clothing that excites you and makes you feel alive!

Anyone can learn to dress better. You just have to want it. It begins tomorrow morning when you step out to meet the world. What will your story be?

Harpers is thrilled to welcome accomplished writer, teacher, and fisherman Bill Kavanaugh to our team. Find his insightful and vivid commentary here on the Harpers blog.