dressing to impress

In advance of our trip in a couple of weeks, I've been reading a ton of different threads on user forums like TripAdvisor, Frommers, and Fodors about restaurants on the Big Island and am finding a wealth of information. One thread that received the most commentary was about proper attire for a fancy dinner at the Four Seasons Hualalai and what was and was not appropriate options.

It wasn't clear from the original post, but I - and others - got the impression the person was asking if tennis shoes would be okay and this derailed the thread into a conversation about being judged by hotel staff based on the clothing and accessories you have. A few people acted quite offended to hear that they might be judged by a maitr'd or the front desk staff which I found absolutely hilarious and naive. Of course you're judged by how you look - that's the society we live in!


I was actually really afraid of this for our first trip to Maui and the Big Island for our wedding. We were young and we were spending the absolute maximum we could to have a high-end experience that we'd remember for the rest of our lives. We wanted luxury, but did we look like we could afford it? Probably not. First, we were young. The diamond on my engagement ring was a little over half a carat (we've since upgraded when it cracked - yes, my diamond cracked!). We aren't fancy dressers. There was nothing about us that would have told the lady checking us in that we were VIPs except for the fact that we were getting married at the hotel. I think because of that we were given a better room than what we had booked. Our "garden view" came with an ocean view. Days later when we checked into our hotel on the Big Island we were given a shit room overlooking a construction zone. We asked to move but were told we couldn't. Given the events of 9/11 just months before the hotel was hardly at capacity, but we were young and clearly not rich. There was no reason for anyone to go out of their way to extend any upgrades or pleasantries to us. I get the game.

Now, I've often talked about how I loathe to dress up. I'm a bigger girl and can't wear a lot of the fashionable styles. I do most of my shopping at Gap, Old Navy, and Target. I am clearly not what you'd call designer. And Alan? Oh boy. He's still wearing shirts he got when he was 20. During the winter it's a bit different because I can convince him to wear a collared shirt with a nice sweater, but in the summer he doesn't put much effort into his look. Why should he? Who does he need to impress?

A couple of years back we walked into the Mercedes dealership here in town and were virtually ignored. I say virtually because I saw the man on the floor look at us and decide we weren't worth his time. We went to open houses when we were looking to buy our house and the same thing happened. Simply put, we do not dress to impress. Funny enough, we walked down the street and got a Saab instead. No one there cared how we looked, just that our credit was excellent.

But now? Well, I have nicer accessories now and people seriously notice these things. It's insane!

I kid you not, we walked into a pharmacy in Paris and were treated with derision and scorn. I turned my head to look at Alan with a WTF look on my face and the young Parisian hipster saw that my glasses are Prada (not Prado). Suddenly he was nicer and helpful, going so far as to comment on my designer glasses. And I do it myself! I've already written about how having my Chanel glasses in Ireland at Ashford Castle made me feel better about myself when surrounded by ladies in cheap sequined dresses. Yeah, I wasn't dressed up, but I knew that my glasses cost more than their entire outfits and that made me feel better. Shallow, but better.

I carry a large, basic black Coach purse everyday (not the one with the giant Cs all over it) and I've had sales people in stores comment about how much they love basic black leather bags and then give me better service over someone carrying a bag that was clearly not from a designer brand. Personally, I think the brand value for Coach has gone way down (when 12 year olds can afford to carry your line, you've gone down market), but I love the style of their purses so I continue to showcase brand loyalty. But to get better service because I am carrying a Coach bag? That seems preposterous.

And since I've gotten my larger diamond? Yup, better service. The ladies who do my mani/pedi will remark on my "pretty ring" and give me a better foot massage. You know why? Because they think I have more money for a tip. But here's the wrinkle in their assumption - my diamond isn't actually that large. In fact, it's smaller than any of my married friends' diamonds. The fact of the matter is that I have teeny tiny carny hands and so a 1 carat solitaire looks big on my size 4 finger. Put it on someone that has regular sized hands and it'd be just another ring.

As far as dealing with being sized up at the Four Seasons Hualalai, I do have some experience with that. In 2009 we ate at Alan Wong's Hualalai Grille. We showed up looking like two people in the middle of vacation - Alan was in tan linen pants and a Hawaiian shirt, I was in a strapless sun dress with fancy sandals. I didn't have any makeup on, didn't carry a purse and my only jewelry was my wedding rings. In a place like the Four Seasons 1 carat is like dust. I know this. I'm not dumb. We were immediately seated next to a family with two kids that were acting like heathens. Of course they sat us in the worst table in the room. There was nothing given our appearance to do indicate we should be treated otherwise.  Compared to their regular clientele, we were downmarket. Or so they judged us to be. Then we ordered the most expensive thing on the menu and suddenly the service was MUCH better and we were moved to a perfect table away from the young hooligans. At a place like the Four Seasons money talks and if you think it doesn't you're kidding yourself.


But that's okay. I'm perfectly happy with the lifestyle we've chosen and the purchasing decisions we've made because that's what ensures we take three amazing vacations a year. For the price of a couple of pairs of Manalo Blahniks or Jimmy Choos Alan and I will be hanging out in Hawaii. And we probably will have gotten there on reward points. Yup, I'm just fine with this.