Style Do’s and Don’ts for dating
If you came here from any other part of the dating do’s and don’ts series you will know that this is the one of the posts where we give specific clothes recommendations. This post is about good jackets, hair and knitwear. For links to the other posts on skincare, shirts etc see the bottom of this article.
For the where-to-buy references for the clothes and products recommended here, see the listings at the bottom of this article.
For our American readers
We have a lot of readers in the US and I need to point out that a number of the brands we refer to in these articles are based in England. So wherever possible we have put pictures of the clothes or products, so it is possible to understand the point of the recommendation. Recommendations for US brands that produce similar clothes / products are happily accepted as comments on the article.
No 5. DON’T: Cotton Jackets. DO: A tailored jacket
Cotton and Cotton denim jackets – awful.
So back in the seventies they had flairs, which made most men look like dicks. The modern equivalent is the cotton jacket. These are jackets cut as a standard suit jacket, but made out of cotton, or poor quality cotton denim. They are supposed to be a look that straddles casual and smart casual. I see lots of Englishmen wearing them. They are an economy buy and they look really bad.
It’s a question of tailoring. These jackets are cut on a standard block and meant to be worn tight, which is where it becomes stupid. Cotton, unlike wool and silk, does not “give”. Wool has the capability to expand slightly and accommodate your body shape, cotton does not. So these jackets sit awkwardly on anyone who is not a perfect shape.
Worse, is these jackets deform very quickly. Unlike a real jacket they have no internal canvas, and are held together with large, visible and ugly seams. These are under the arm down to the hip, parallel down the shoulders. If you are really unlucky they are also seamed down the chest, down through the pectoral. So when the fabric gets damp (perspiration, rain) and then dries, the cheap seams contract and bunch up. They pucker and bend, the thing SHRINKS. This is beyond crappy, you look like you bought the wrong size. The skirts lift and the chest compresses, so the overall effect is that you have a puny chest and a fat arse sticking out.
Even worse is that these things are designed to colour fade. So you get some washed-out shade of blue, green or brown, which in turn makes you look washed out. Lots of men think that these are a substitute for a good sports jacket or a good leather jacket and compound the error by wearing them for years, when their useful life can be measured in weeks (at best).
Also, unlike wool, they do not wick away perspiration and other odours and the bleaches used to give them a semblance of being a garment often smell too. These things SMELL BAD.
If you turn up on a date wearing one of these you send a subconscious message that you are cheap, inconsequential and physically misshapen. If you buy one you should have “Loser” tattooed on your forehead.
When I spoke to women about these jackets I was struck by how much they hate them. One woman friend described them as “as bad as shell-suits ” (nylon sweat pants and tops for our American readers).
I saw this guy wearing one of these and it was as bad it looks. I shot it from behind, partly to ensure his anonymity.

Cotton Jacket
The jacket really did rise up on the left side, its not a Photoshop trick. It is wrinkly and ugly. The mad thing is that this guy was fit and good-looking. However wearing this crumpled mess ruins his look. And, I am sorry to say, it did smell.
The Deathzone
One of these horrible jackets with colour-faded jeans. Cheap and nasty beyond redemption.
Real Jackets
So every man should have at least one good jacket, they are so versatile and useful. For dating, they are essential. Women find a defined silhouette really sexy and the way to get one is to wear a good jacket. TThis works especially well if your body-shape is not perfect, a good jacket re-frames your outline/silhouette into something that women find attractive.
And lets be clear about jackets, what I mean here is a conventional classic jacket, with lapels and some internal; structuring. The material should at least be wool. Silk, cashmere and other luxury fabrics should be considered an advanced class. Finally, just to be clear, we are talking about off-the-peg here.
Which way to go? English, American or Italian style?.
Which of these national styles suit you? Here’s a very short summary of how these jackets work.
English
Long, slim cut, high proud straight shoulder, gives you a very hard silhouette. Commanding, high status and slightly old-school. Lots of wonderful fabrics, wool worsteds, tweeds, but a fairly restrained colour palette.
Combinations English jackets have a lot of structure and symbolic history, so can be paired up with lots of other clothes. They are the only jackets that can be successfully paired with jeans, in my opinion.

Hackett wool worsted jacket
Great for the man with the classic figure, wide chest, small waist. Really good for the tall skinny man, if tailored correctly (see tailoring, below).
American
Long cut, cut broader in the chest and waist. More forgiving overall, still a definitive silhouette, but slightly more relaxed. Fabrics are often plainer, without the texture of English jackets and a wider, if simpler, colour palette.
Very good for the bigger man. Gives an acceptable shape to men who are overweight, but remember, it’s a jacket, not a miracle, it won’t turn you into Brad Pitt.

Jacket from the superb Brooks Brothers
Combinations. American jackets can be a little staid, so wool trousers and a good shirt works here.
Italian
More rounded, curvy shape, sinous and sexy. Sleeves are narrower, making Italian jackets (and you) look lighter and slimmer. Wonderful fine wools, much more daring colours.
Great for the shorter man or for a man with an unconventional shape. Italian jackets can look a bit tight, a bit silly, on tall men. If you are a big man you need to be careful when buying an Italian jacket. One tip is to ask for a size larger than you normally wear, try it on and go up and down from there.

Canali Jacket
Combinations. Really good with chinos, good quality wool trousers. Work well with knitwear (instead of a dress shirt) underneath.
Tailoring
Your jacket needs to fit. Off-the-peg jackets are built for a standard size dimension. Sometimes you can buy a jacket off the peg and it fits perfectly. This is incredibly rare, it has only happened to me twice in a lifetime of buying good clothes.
So when you buy it off the peg, have it tailored, it is really worth the money. The better your jacket fits, the more attractor signals you will send to your date’s subconscious.
There are two essentials.
Chest and waist. Especially for tall men, the chest and waist should be tight, with jiust a little room to manoeuvre (enough to get a shirt and a fine knit sweater underrneath). The outline should be sleek and streamlined.
Test it. Look in the mirror when you try it on, turn around. If the jacket “swivels” around your torso and the skirts flap around then it needs tailoring.
Wrists – English or American?
The English style is to show a little shirt cuff. The American style is for the jacket cuff to completely cover the shirt cuff.
Getting wrists right is vitally important. If the sleeve is too short and you have half your forearm sticking out, it looks stupid, and to be honest, it looks poverty stricken. If it is too long, covering any part of your hand, you look a bit clueless, like a little boy.
Test it. When you try a jacket, be sure you are wearing a dress shirt that fits you well at the cuff. Look in the mirror, where does the jacket cuff fall? Bend you arm at a right angle. Where is the jacket cuff?
Structured versus Unstructured
Unstructured jackets are very popular right now. They are lighter and easier to wear, cooler in warm air-conditioned environments. Structured jackets have a canvas (inner chassis) which helps them hold their shape. Also some jackets rely on the canvas to provide a foundation for the complex stitching that gives them their shape. The high hard shoulder in an English jacket that gives it that manly shape relies on a classic canvas.
Basically a structured jacket with an inner canvas will hold its shape longer, last longer and better. That said, the light feeling of an unstructured jacket is great and give you an entirely different attitude. The choice is yours.
But please, no cotton jackets.
Making it yours
This is old school but still true. When you buy a jacket it is new and the first time you wear it, it looks “new” and a little raw, a little odd. You want your clothes to look comfortable on you, you want a personal style. So remember that a jacket needs a few wears before it settles “into shape”. This means it subtly conforms to your unique individual body shape.
A good jacket helps define your style. Enjoy finding a good one.
No 6. DON’T: Umkempt beards, dirty hair. DO: shaped, groomed beard
Beards
A lot of women find beards sexy. Studies show that men who wear beards are felt (by women) to like themselves, see their appearance as important and want to stand out from the crowd. For this reason many women are attracted to men with beards. Women friends of mine like men with beards.
But it has to be the right beard.
The studies also found that the positives only applied if the beards were well-groomed and maintained (clean). So your beard has to have a defined shape, it has to be clean, it has to be soft. If it is hard and spiky and you kiss her and it tears her lip, well, once again, game over.
The Deathzone
This is absolutely how not to do it – homeless person.

Brad Pitt with beard (kind of)
Beards done right and good hair

Ben Affleck with a well-groomed beard
This is easy enough. Beard trimmers are a necessity. I use a Phillips Turbovac, which has the fine blade settings I like. The vac part is really efficient, I have never had to resort to cleaning beard hairs off the bathroom floor. If you have a beard, you must groom it before a date. Trim before you shower, you get a better cut and a better finish.

Phillips Turbovac Q4040 Beard Trimmer
Beard shampoos are useful, Beard softeners are essential, if you are not going to pincushion her face. I like the Beardsley range of products. They are harder to get in England but lots of internet companies sell them.

Beardsley Ultimate Beard conditioner
However what really works for me above all else is the classic Moustache Wax from Taylors of Old Bond Street. I use this on a daily basis. It is fragrance-free, easy to work in, invisible once on and gives just the right amount of hold. It also softens the beard. Which is of course essential when kissing women…. Nothing spoils the mood more than your beard pricking her in the lip.

Moustache wax from Taylors of Old Bond Street
Tip
The thing that makes your beard spiky and sharp is cutting it to shape with a razor. So after shaving, trim you beard with a beard trimmer or, if you need something smaller, use a pair of fine scissors.
Shaving (and shaving around the beard)
I promise a full article on shaving another time but for now really just a tip. Use a shaving gel not a foam. Foams often contain synthetic chemicals which dry and damage your skin. I always recommend a shaving gel because by working the gel into your skin you get a better contact between the emulsion and the area to be shaved. If like me you wear a beard I recommend a clear shaving gel. It makes it so much easier to see what you are doing and shave into the line of your beard. Precision is called for, and a clear gel helps prevent you accidentally chopping out a chunk of your beard.
Your Hair
As with your skin, your hair is a factor when you get into the closeup zone. It must be clean, hair has an unfortunate capability to trap smells. A good haircut should give your hair texture and movement. If you have good hair, obviously wax and styling gel will give it shape. If you are folically challenged, get a good tight haircut from a good barber. You need to experiment here, but a good barber will give a short haircut texture, which you can improve on with a good (fine) styling gel.
There are too many products to list here, so just some brief recommendations.
I like organic products without Parabens or other petrochemical additives. My hair is naturally fine (for a man) and I need something that I can use regularly without stripping the oils out of my hair. I use the Jason Aloe Vera range, both the shampoo and for styling the ultimate gel.
No 7. DON’T: Baggy knitwear. DO: One good sweater
There are several problems with knitwear with regard to dating. Truthfully, doing knitwear well on a date is hard. My suggestion is to follow the guidelines below.
I learnt the hard way that dress-down knitwear, big cable-stitch sweaters do not work for me. And though they work really well as part of a natural, casual look, that look does not suit many man. Sure, most brands promote that look, because selling you natural-style casual clothes makes brands more money. But the truth is that we are mostly urban folk now and we do not wear that look well. I have a friend, Tim, who is about six foot four, broadchested, strong, masses of red-blond hair, rugged good looks, looks like a Viking just dropped out of a time machine (curse him). So Tim looks good in rugged cable-stitch sweaters, most men dont.
Knitwear is expensive, deforms easily, damages easily and is difficult to do well unless you know what colours suit you (back to the colour analysis again).
So some rules of thumb are:
If knitwear is old, do not wear it on a date.
Fit is very important. it is a key factor in making a visual impact on your date. Old kintwear will be baggy, misshapen and suggests you are an odd shape.
Do not wear knitwear on a date without washing it.
Knitwear harbours smells more than any other clothing. Women are acutely conscious of smells, on both the conscious and the subconscious level. I cannot emphasis this enough. Women are driven by their emotional states. If you smell bad, you will soon change her emotional state to one where she simply wants to be away from you. You can dress like a bad boy but if you smell like one you are finished.
Every Autumn I take all of my knitwear from the wardrobe and wash it. I have built up a collection of good (and often expensive) knitwear so it takes time and care to wash it. But it is worth it. Apart from anything else, knitwear that has spent the summer in a wardrobe, is dull and ”flat” looking. It needs pepping up.
Buy knitwear that fits
I once went to Gemelli, the famous knitwear shop in Milan. They are the only men’s knitwear shop I have ever been to, where it was possible to buy knitwear by chest size. Superb. However in England and America it pays to experiment, because “small” ”medium” and “large” mean different things to different brands. Oversized knitwear makes you look stupid
The Deathzone
Baggy, smelly and old. Knitwear. Women complain that they meet men who are weak and need looking after. In style terms, nothing says ineffectual and weak as plainly as crappy old sweaters. The corollary to this is giant cable-stitch sweaters on small men, 25lbs of wool on a man who only weighs 110 lbs. Mummy’s boy.
Good Knitwear
Know your style
Fashion is no guide here. Types of knitwear goes in and out of fashion, but the fundamental truth is that all styles are wearable, but you have to know your style to do them well. The other problem is that knitwear sizes are so variable. In my view, it is impossible to buy good knitwear on the Internet, unless you trust the brand’s returns policy. You have to try it on.
Good knitwear Brands
You gotta find them and cherish them. In England I like Daks (superb), Linea, Uniqlo, Ermangildo Zegna (Esp. the Roll-necks) and John Smedley.
Crewneck sweaters
The standby. They suit most men. If you have a belly, they are good at hiding it, especially in darker colours. The danger here is in buying too large a size, in which case you look like a shapeless mess.
Tip
Wear a dress shirt when you try on the crewneck, one that you know fits you well . There should be enough space under the crewneck to wear the shirt comfortably. Too tight, and you have the buttons on the shirt placket sticking up like a row of vertical nipples. Too big and you are back to the shapeless mess.
Here is a superb Uniqlo cashmere crewneck I picked up the other day, for very little money.

Uniqlo Cashmere Crewneck
Mock-Turtleneck
These are back big-time, courtesy of Steve Jobs. I have a lot for time for turtlenecks, they are classic, easy to wear and confer real style (remember high status rules) when worn under a good jacket, Italian for preference. The only problem is getting a good neck and body fit, you do not want this type of sweater to be too loose, it statrts to look a bit smock-y. Here is a classic from John Smedley;

John Smedley mock-turtleneck
V-Neck
V-necks are surprisingly difficult to wear. If you are a big guy, the depth of the gorge (the V) can be a problem. Too deep (and wide) and it looks like you are busting out of your clothes. Too small and it looks like the sweater is strangling you. Also, in England at least, v-neck sweaters have enduring connotations of preppy schoolboys, so you have to be careful with v-necks, they can make your look seem pedestrian and timid. That said, a well-fitting v-neck is the prefect sweater for a compact guy. V-necks are very much try before you buy.
Here is a v-neck from Linea, a brand I like for their good finishing and inventive colouring;

Linea v-neck sweater
Knitwear for dating
The rule of thumb here has to be sweaters that fit, that are at minimum clean and to be honest, as new as possible. Solid (single) colour would be my preference. Multi-coloured sweaters are too difficult to match up to the rest of an outfit.
More in this series
To read the other articles in this series:
Part 1: How clothes work on a date, is here
Part 2: Shoes and black shirts, is here
Part 3: Good skin and bad t-shirts, is here
Part 5: Smell, look and attitude, is here
Men’s Fragrances: How to choose them, is here
Men’s Fragrances: 20 Good Fragrances reviewed, is here
Details
Jackets
Hackett English ready-to-wear style is here
Brooks Brothers is here
Canali is here
Beards
Phillips is here
Beardsley is here
Taylors of Old Bond Street is here
Knitwear
Daks is here
Ermangildo Zegna is here
Uniqlo is here
Linea is here
John Smedley is here
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