I was watching Spectre the other day, you know, the annual Christmas James Bond watch-through (everyone does that, right?). Anyway, as I was watching it, I took note of the train scene. No, not when Dave Bautista shows up and beats him to a pulp. Before that, when Madeleine Swann walks up to Bond. I took a look at what everyone was wearing. Because, of course, I did. And took note that while everyone else is dressed as you would expect a man and woman to be dressed in 2025, James Bond is in a black tie ivory dinner jacket, and she is dressed in a sleek evening dress. Are they overdressed? Is there such a thing?
Recently, I got the opportunity to escape the cold weather and go to the Maldives and visit three resorts in the Sun Siyam portfolio. I got to see what they have to offer. (Spoiler alert) They offer the best experience in the Maldives. I spend a lot of time in the Caribbean, and the biggest difference is the Indian and Asian influence instead of the European and Central American influences we have on this side of the pond. Oh, and let’s not forget the over-the-water villas. But the group that I was with had dinner together every night, and I always dressed up. It may have felt a little weird being the only one most nights, but that would never stop me. The truth is, men have traditionally (in the civilized world) dressed much more elevated for dinner. So, should you? Hell yes, you should. And here is why.
Why you should dress for dinner
Let’s start with the obvious: after six pm is when evening wear is expected and/or accepted. Parties, drinks, dates, all require getting dudded up and looking your best. So why do we change that? Why do we stop dressing up for our significant other? Why do we lower the level of our dress as we get older and are less focused on our appearance? Laziness and complacency are two explanations. But the more common one is that we just grew out of it as a society. We got more casual in some places, and that permeated everywhere else. Well, no more. There are only three reasons someone invites a man to dinner:
- They need something from you – a favor, an apology, advice or counsel.
- They want to give you something – congratulations, an apology, advice or counsel.
- They simply want the pleasure of your company – date, catching up, weekly dinner.
All three of these situations require a man’s best. There isn’t one of those situations where it is respectful to show up underdressed. They want you at your best, and you should give it to them.
The message it sends
Let’s talk about the message you send. Imagine you are invited somewhere (or you invite someone else) and they show up dressed like they just woke up, or just got off work, and came straight from the construction site. They put no time into spending their evening with you. They don’t seem to care that they are about to have a lovely evening with you. They seem to simply be there for the free food. You send a message with your appearance, whether you know it or not. And when you dress well, you’re showing that they have your attention and they are important to you.
When I was in the Maldives, Sun Siyam resorts were packed full of restaurants, bars, and shows to keep me occupied. It was also packed full of people coming in off the beach for dinner. But when I sat down at my first-ever authentic Thai restaurant, or when I stopped off for chicken parmigiana soup (yeah, it is as good as it sounds), I was dressed up. Nobody else was, but I was. And here is the thing: what everyone else wears is none of my business. I wear what I love, and I dress for the moment, because the moment deserves me.
Tips to not overdo it
Now, is there such a thing as being overdressed? Yes, there is. Obviously, unless Sun Siyam was throwing a black tie event, I wasn’t going to wear Bond’s ivory dinner jacket. However, I was going to elevate with a jacket. You shouldn’t have dinner without a jacket or a tie. Now, I say or, but if you’re wearing a tie, you do need something over the shirt. Whether you go with a sweater, a cardigan, or the always beloved jardigan, you shouldn’t wear just a tie with a shirt. It makes you look a little too much like an IT professional on break. When it comes to the pants, you can wear dress pants, but I tend to love a dark, dress denim or a pair of chinos when I am in a tropical environment. However, if you are in your hometown, dress pants are a perfect evening companion. For the shoes, toss the sneakers and rugged boots to the back of the closet. The shoes will make or break this outfit. Get your derbys, oxfords, or chelseas and look great for your company.
This isn’t a rule. Nobody is going to throw you in jail if you wear something casual to dinner. It definitely isn’t a rule at Sun Siyam. They are going to treat you like royalty no matter what you wear. But if you are going to go all the way to the Maldives, celebrate the time by dressing up. Be your best self.
