5 Winning Holiday Styles – Be the Best Dressed Man

Holiday style checklist for success and style this holiday season.


A few weeks ago, this column featured strategies and style suggestions for holiday dressing styles for women. As promised, now it is your turn, gentlemen, to get actionable suggestions to elevate your holiday style. Don’t you also want to look your very best for professional office parties, family dinners and social “holidates”? Don’t you want to feel confident and comfortable, and make a lasting impression?

The first thing to keep in mind is that holiday events are different from regular family, social or professional gatherings. They are festive and special, and that’s how your outfit should be. Don’t just wear your default jacket or work attire. Dare to own the festive and special in you.

Here is a preliminary checklist, followed by a success strategy and style ideas to dress your best for holiday engagements.

Preliminary Checklist

1.   Think FIT

Think about your body and what fits you well. Not too big, not too tight – just right. Fit is essential for everyone, but more so for men. A well-tailored outfit makes the difference between being the best-dressed man and the sloppiest one.

2.   Think context

Taking account of the crowd and the location is the key to striking the right look. Is it a family event with kids? A business dinner? A social “holidate”? Where? Is there a style/dress code expectation? How’s the weather?

3.   Think comfort

You will be sitting, standing, talking, dancing, drinking and eating! Your outfit should allow you to enjoy yourself. If you are uncomfortable, you will have an awful time, and your body language will show it. Comfortable and sharp-looking are not at odds.

4.   Think details

Your whole outfit should be polished and curated – including belt, shoes, and, if need be, nails and hair. Style is in the details!

Once you have these down, you are ready for a success strategy and suggestions.

Success strategy

Perfect shoulder and pant fit + special festive detail (overdo it a little!)

Five winning style suggestions:

1.   Well-structured jacket + smart shirt:

For any professional holiday event, a well-structured and good fitting jacket is a must. If formal, it should be part of a suit –  a classic midnight blue will have you covered. If you are heading to your holiday event from the office, change your work shirt for a shiny and deep-colored light-weight chambray shirt for a festive feel (please make sure your undershirt is not visible!). If a suit is not required, you can pair your jacket and smart shirt with corduroy pants or jeans. Choose shoes and belt accordingly to create a harmonious look. For example, you could wear tan or black boots with corduroy or jeans.

Next- Winning styles 2 through 5

Mara Kolesas
Mara Kolesas
Mara Kolesas, Ph.D., is a style with substance expert, based in Berkeley, CA, who provides intelligent styling for professionals. She grew up in Buenos Aires where she breathed style from an early age. She went on to a career in political science, studying for a doctorate in New York City, and later lived in Florence, Rome, Berlin and Beirut, where she pursued my two passions: she studied and promoted citizen empowerment, diversity and inclusion, and she explored small boutiques, helping friends find outfits that gave them joy and confidence. Along with her artistic eye and knowledge of fashion, she brings analytical and social expertise to a field with superficial associations. Twitter