I Own Five Hats. Four Of Them Live In A Drawer. | The Weekend Gentleman
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I Own Five Hats. Four Of Them Live In A Drawer.

Let me save you the money I wasted.

Over the past four years, I have bought a $52 Harris tweed cap because everyone recommends one, a $45 Tilley wide brim, a $34 Kangol newsboy sold as "one size fits all" that was not, and a $22 ball cap with another company's logo across the front, and I still leave the house bare-headed most days.

Four failures. One winner. Here is the difference:

Note: read this BEFORE you buy another cap that ends up in the drawer.
Kevin Cooper
Kevin Cooper
Style Desk, The Weekend Gentleman

Reason 1

It tightens at the sides, not at the back

Side buckle adjuster on the denim flat cap

Pull a strap at the back of a cap and you do not make it bigger. You drag the back panel forward and squash the sides.

This one carries a small buckle on each side instead, so it opens and closes evenly around the whole head. I have a large head. It is the first cap sold as one size that has ever actually fit it.

👉 See the side adjusters

Reason 2

Ten minutes in, you stop noticing it

Inside of the cap showing the soft cotton lining

Every one of those hats announced itself. A ridge across the forehead. A pressure point above one ear by lunchtime. You take the thing off in the car and there is a red line where it sat.

I put this one on at nine one morning and remembered it at two, in a shop window. That is the whole review.

Reason 3

It stays on in wind

Back of the denim flat cap, showing no rear strap

Anything with a brim catches air. Anything that grips only at the back lifts at the front. My wide brim has been chased across two car parks and I have stopped taking it out.

This one sits low and closes the whole way round. It has had a fair few chances to leave my head and has not taken any of them.

👉 See the cap that stays put

Reason 4

There is no button on the crown

Front view of the denim flat cap showing the flat crown

Most newsboy caps finish with a covered button where the panels meet. With a full head of hair you will never think about it. Thinning on top, it sits on skin and you think about nothing else.

This crown is flat. Nothing in the middle. I did not know to check for it until a reader wrote in and told me to.

Reason 5

It reads as dressed, not as trying

Older couple walking together, the man wearing a flat cap

Plenty of men will tell you a flat cap ages you. I get the letters. I am not going to pretend otherwise.

But a cap that is too big sits on a man like a lampshade, and that is the thing doing the ageing. One that fits does the opposite. It finishes an outfit the way a decent pair of shoes does. The difference is not the style. It is the fit.

Summer Sale

Half price, and the shipping is on them

$60$30

I was sceptical too, and I had four reasons in a drawer to be. With free shipping and 100 days to send it back, the only thing you are risking is a trip to the post box.

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Reason 6

Denim, so it works in July as well as November

Man wearing the denim flat cap outdoors

I hesitated over buying a wool cap in summer, and I was right to. Tweed in August is a small punishment, which is why my tweed cap spends two thirds of the year in the drawer.

This is cotton denim over a breathable organic cotton lining. It has been out with me in July and it has been out with me in November.

Reason 7

The peak is short enough to see under, long enough to cut glare

Profile of the flat cap showing its short flat peak

Peak length is the detail nobody shops for and everybody notices. Too long and you are tipping your head back at road signs. Too short and it does nothing at all. This one is cut short and flat, and I have stopped hunting for my sunglasses on the drive home.

One honest limit: it does not cover your ears or the back of your neck. If that is what you are shopping for, buy a wide brim and wear it happily.

Reason 8

It replaces the drawer instead of joining it

Men wearing their Harrington flat caps

The test I apply now is not "is it nice" but "what does it retire". A cap that earns its hook has to push something else off the shelf, otherwise you have not bought a hat. You have bought another hat.

This one retired the ball cap in a week and the tweed cap by the end of the month. They are the two in the drawer that used to get worn.

Reason 9

Six colours, so one goes with what you already own

Tap a colour to see it up close.

Colour is what I dithered over longest, and it is the wrong thing to agonise over. The rule is dull and reliable: pick the colour of the jacket you wear most. I went denim blue. I am now eyeing the olive.

Reason 10

It costs less than the hats already in your drawer

Man wearing the denim flat cap in a garden

The four hats I do not wear cost me $153. This one was $30, down from $60, with the shipping included.

I will name the other hesitation plainly, because I had it myself: buying from an advertisement on Facebook. What is checkable is that returns run 100 days, shipping is free, and the one and two-star reviews are still sitting there in public under the company's name. I read a few of those before I ordered. It is usually more informative than reading the good ones.

Summer Sale • 50% Off

Ten reasons, one cap, 100 days to decide

$60$30

Six colours, one size with the side adjusters, free shipping, and a full 100 days to change your mind. If it ends up in a drawer, it goes back instead.

Yes! My Everyday Cap
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