John, Los Angeles: Many of my colleagues laugh when I tell them I often pick out five days worth of clothes on Sunday evening. But I find that taking the time to select outfits for the week on Sunday and actually hanging them in the closet makes my mornings much calmer.

It also allows me time to really explore and ‘shop’ in my closet, and to put together, even try on, new combinations. It also reveals possible repair or cleaning issues while there is still time to do something about it. If my schedule for the week changes, with certain meetings requiring different selections than I have already prepared, I still have the flexibility of moving days around.

I find that the whole enterprise keeps me from just reaching for my favourites and makes me look forward to getting dressed each morning. What are your thoughts?

I strongly agree with two of John’s observations. First, I never have time enough to think calmly about what I will wear that day, let along try on one or two options. Second, thinking about what I will wear in advance opens up many more possibilities. My imagination has more time to whir through its collective memory and the wardrobe permutations.

The first of these is a real pity. As Patrick Grant at Norton & Sons observed to me recently: “It is a real shame that men don’t take 10 minutes every morning to think through their clothing options. Even if it’s just to try on two or three different ties.”

But I have to say I never fail to know what I am going to wear in the morning. Such is my passion for all things sartorial, and my eagerness to experiment, that I have already put together two or three possibilities in my mind. The evening before is normally the time for this and, if I can’t decide, I lay out a couple of options to let them stew.

Indeed, such are the whirrings of my mind that I normally have more combinations than I need. This week, for example, was forecast to be bright sunshine for at least four days. To each of those days I therefore allocated one summer item I would like to wear – new unlined navy blazer; cotton/linen trousers in a strong blue from Florence; spectator shoes from Lodger; and a tan linen jacket/yellow tie combination. Except that two days later my mind had come up with more ideas and some had to fall by the wayside. How about those white trousers? Or the cotton jacket? You never wear those when it’s sunny.

To those without this near-obsessive bent, I recommend John’s approach. At least plan out two or three days. There will always be a day or two where you are out in the evening and don’t have time to plan, in which case you can reach for old favourites. But if there’s no time given to considering your clothes, there’s unlikely to be any joy in it either.

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One of the best habits I have is one that I acquired as a boy: laying out my clothes the night before. True, I am always perfectly dressed for yesterday’s weather but not always for today’s, but other than that, it allows me the time to plan what to wear and select an an outfit. But selecting a wardrobe for a week? Wow! I only do that when I travel. Great idea, though.

How do you build your day’s wardrobe, Simon? I find that I pick my tie first and let it determine the shirt, which then affects which trousers, which in turn decides the jacket (if I haven’t selected suit trousers, that is). Pocket square is last. I’d be interested to know how others put together an outfit.

Sinatra's Shadow


An excellent blog, and I believe from reading it that you are very much at the same stage of your sartorial development as I am, which makes for particularly interesting reading.

One question, if I may be so bold: what is your day job? I understand it is in the City, but in what field? I only ask as to shed some more light on the opportunities and restrictions available to you when dressing, and in order to compare them with my own.




Thank you for answering my question. Here’s a new one:

Do you ever find that you always wear a particular set of clothes together? If so, how do you break them up?

I have a certain blue club tie that I always pair with a blue Oxford buttondown, which then always gets worn with a pair of darkish mid-blue trousers, which go perfectly with my gray & blue herringbone tweed jacket.

While it’s a good combination (well, at least I hope it is), it is predictable. If you got into a sartorial rut, how would you break it up?

Sinatra's Shadow

Thanks for the insight Simon. I am familiar with IFLR as I am a corporate finance lawyer. You have a very interesting sideline going here.