Fashion advice: What to buy and what to pass

Whatever you buy, though, my general rule is see it, try it, and then think about it for a while.


Q: I am a fashion late bloomer who finally has the income (and self-esteem!) to invest. With all of the high-end resale shops popping up, it’s easy to just throw cash at every shiny/hip new thing and overload my closet. But I don’t want to load up on stuff I’ll wear once and then feel bad about having spent the money on it. My question: What to buy and what to pass?

A: What you are trying to do is create a sustainable wardrobe, a term I have long thought makes more sense than sustainable fashion (fashion, with its constant changes, is by definition not sustainable).

That implies certain things: good fabrics (which last), good design (ditto) and a certain amount of strategic planning. It doesn’t necessarily imply brand names, though it does tend to imply greater cost. The idea is to choose wisely enough that said outlay will be amortised over time.

Think of them as “staples,” pieces that form the spine of your closet and that you can wear over and over again in multiple ways. What are they?

My top five:

1. A sharp black jacket, which can be worn with jeans, onstage during a conference, with a dress, with black pants as a tuxedo and so on. Get a razor-tailored style with defined shoulders that will elevate everything you wear (and also help with the power posing).

2. A great wool or cashmere coat.

3. Good boots. Biker boots or knee-high numbers, in supple leather.

4. A stretchy knit dress, ideally without sleeves so it can be worn with a bodysuit or thin knit underneath when it is cold, and perhaps just a cardigan (or the jacket) when it is warmer.

5. A perfect crisp white shirt, seamed for a woman, with French cuffs. Once you have these items, you can add to them over time. Whatever you buy, though, my general rule is see it, try it, and then think about it for a while.

Updated: 24 November 2020.

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