The Gentleman's Guide

The gentleman's guide  |  Women  |  Style  |  Grooming  |  Decor  |  Culture


First things first; by jacket I mean sports jacket (like the top half of a suit). This is an essential item for a gentleman to have in his wardrobe and it really sets you apart from the crowd. Sure, your hoodie might be incredibly comfortable, but it does nothing positive for your appearance. A hoodie is a shapeless blob (with, of course, attendant ASBO connotations). Wear it on Sunday mornings to nip to the corner shop for milk and a paper, not when you want to look good. What every gentleman should know about jackets is:

  • Why wear a jacket?
  • Where to wear your jacket.
  • What to wear it with.
  • Which jacket to buy.
  • How to button the jacket correctly.

A good jacket is the opposite of a hoodie. It's cut to make your shoulders look broader, your back straighter and your waist thinner. It seems like lots of guys can only picture wearing a jacket at some sort of semi-formal dinner but the truth is it can be adapted to several different occasions. Jackets don't even need to be particularly sober or sensible. Below are two fantastic jackets from my own wardrobe. On the left is one by Holland Esq that has little red 'X's stitched in various places all over it (pockets, buttonholes, collar, etc.) and which buttons all the way up at the front. The jacket on the right is a blazer from Topman, with bold grey stripes and beautiful lining.


Neither of these is anywhere near as sensible as one of my suit jackets, but the way they look still benefits from good tailoring. So where do you wear a jacket like this? Well, I wear them to the pub, to bars, if I go to a nightclub, to performances at the theatre (though be careful here - if you're seeing Chicago it's fine, if you're going to see Faust at the opera then you should be dressing rather smarter), basically anywhere I want to look my best. Consider a typical nightclub for example. Most men dress smartly by wearing a shirt, but you should be trying to elevate yourself above the average.

You can team the jacket with all sorts of different clothes for different effects too. With trainers, jeans and a funky t-shirt you'll look extremely cool. Stick with the jeans but wear brown loafers and a good shirt and you become smart enough to get past most doormen while still looking like you have a wild streak. Wear it over a turtleneck, or with smart trousers and a shirt, or over a vintage polo shirt with a loose tie. The possible combinations give your jacket a huge versatility for different outings, yet every one will make you look just that bit smarter than any men without a jacket.

When buying jacket you should consider a few things. Firstly, don't go for the most conservative one just because you can coordinate the most different outfits with it. The truth is, most things will go well with a jacket without you worrying about matching colours. That said, steer clear of brightly coloured jackets and stick with navy, grey or black. If you feel that doesn't draw enough attention then get one with pinstripes, chalkstripes, or interesting visible stitching. For summer you might like to try linen but be warned that, as with all linen garments, it will get extremely creased within about ten minutes of you putting it on. Wear it at occasions where this will make you look louche and relaxed, not where you'll just look scruffy.

You need to make sure that the jacket fits properly as well. When you've put it on, put your arms straight out in front of you. If there's more than a couple of inches of wrist exposed then the sleeves are too short. If the sleeves drop more than about an inch and a half below your wrist when your arms are by your sides then the sleeves are too long. Button up the jacket. It should feel snug across your torso but not tight. The bottom of your jacket should fall about six inches below your belt, though this depends on the cut. Since you don't need to get changed to try a jacket on I suggest you try it right there in the shop, then find a mirror and check that it looks good. Keep trying different ones until you find one that fits properly.

One last thing; most of the time you'll be wearing the jacket unbuttoned but occasionally you'll want to button it up. When you do make sure you button it up correctly. If you're buttoning a three button jacket the middle one should always be done up. The top button can sometimes be buttoned, but it's important that you never button the bottom button. For two button jackets, just button the top one. If you have more than three buttons then think about leaving some/all of the top ones undone, or just getting a jacket with less buttons. Why is all this button stuff important? Firstly, the jacket won't hang properly on you if you get it wrong. And secondly, it's like putting your knife and fork in the wrong hands. It's just not done.

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If you're wearing the jacket over a t-shirt then roll the sleeves up to make the jacket look even more casual, though don't do this with your favourite, most expensive jacket.