Dear Kathi,

For starters, I’ll admit that I am clueless about clothes, so please excuse me if this sounds like a dumb question. I have just received an invitation to a party at a business colleague’s home. The invitation reads, “holiday attire welcome.” What does this really mean to me – formal? informal? silly Santa tie? holiday sweater? – or what?
Please help me out, the event is imminent and this is an important business contact for me.

Joe, San Diego


Don’t feel bad about not knowing what to wear to this event. The invitation is cryptic at best. To decide what to wear, we need to discover a few more details.

What type of business environment does the host work in? What type of clothes does he/she normally wear on the job? What is the address of the home where the party will take place? Was the invitation personally or professionally printed? Is the event in the evening indoors or outside during the day?

When an invitation is professionally printed, scheduled in the evening and at a prestigious address, you typically want to dress more formally. If the invitation is a daytime affair set in an informal environment, you have more latitude for casual attire.

Consider closely your colleague’s normal work clothes and status. If always in khakis and polo shirts, the colleague’s event will most likely be different than if he is always in a suit and tie.

As a man, your job of hitting the mark with your outfit is much easier than a woman’s because your choices are more limited. My advice is that you can never look too sharp, especially if this is a business contact that you are trying to nurture.

As a non-suit and tie affair, you can’t go wrong wearing a pair of dark dress slacks, a collared shirt in an unusual color or pattern, (coral, teal, brown, something besides “serious” white) and a coordinating blazer. Make sure your shoes are polished and crisp; in other words, no topsiders.

If your host never wears a suit, you should follow his lead. Wear a blazer in a more casual and relaxed fabric like tweed or corduroy and a pair of dark jeans. Every man, by the way, should own a pair of dark, nicely fitting jeans. This means almost black in color and no holes. These are an invaluable addition to your wardrobe and can be dressed up or down depending on your shirt and shoes.

When you arrive at the party, quickly scan the crowd, If the blazer is too formal, take it off immediately, as if it were an outer coat. You will then blend in with the crowd at hand. NEVER wear the cute holiday sweater or tie to an unknown event. In fact, in my opinion, they should be outlawed. If you still feel overdressed, be aware that you may be the best-dressed man at the event. This is always an asset, especially if you are trying to develop business relationships.

“Holiday attire welcome” might mean that the hosts are planning on wearing clothes with a little more glitz and polish for this event. Again, you can’t go wrong with a blazer. Top your jeans with a nice crisp collared shirt and you will appear put together and sophisticated. Don’t worry if other men in the crowd are wearing funny ties and the Santa sweater that they only wear once a year. Revel in the knowledge that you know they don’t really want to wear those eyesores and that you don’t have a partner who insists that you bring one out once a year!

Please submit your questions to: [email protected].
San Diego Professional Organizer