[COMPETITION]: This list features a competition. See the bonus item for more information.
As the founder I get to take a few liberties with the types of lists we publish. Typically I don’t accept lists about fashion or “general living” tips but this happens to be a passion of mine so today I am taking one of those liberties today.
This list is focussed on tips for men who have need (either regularly or only on occasion) to dress in something other than jeans and a tee shirt. If you are all casual all the time, you may want to skip this and read one of our more cerebral lists of the day (There are four in total today).
This should serve as a guide for anyone needing to know what to wear to a job interview, what to wear to a graduation or first date, or what to wear to a new office job.
If you follow the guidelines in this list you will never be poorly dressed in public . . . I guarantee it.
10 Always Wear A Belt
If your trousers have belt loops, you must wear a belt. Trousers with belt loops and no belt are incomplete. The effect is either one of poverty (you can’t afford a thin strip of leather to hold up your pants) or one of a man who has gained weight and needs to leave as much room as he can for his ample stomach. And your belt should match your shoes: black belt with black shoes, or brown belt with brown shoes.
This photo also illustrates what goes wrong when you ignore item 8 on the list: the jacket and tie have patterns that are too similar in shape and scale making it look too busy. A solid or striped tie would be much better.
9 Don’t Wear A Belt And Braces
This is the opposite of not wearing a belt: wearing a belt and wearing braces at the same time. This screams one thing only: insecurity. There is a really simple way to determine what you should be wearing: if there are belt loops you wear a belt, if there are no belt loops, you wear braces. The ideal braces should attach to your trousers with buttons sewn onto the inside or outside (more traditional) of the trousers, but clip-ons are fine for the following reason: braces are considered to be underwear.
And finally, no one should ever see your braces except you and the lucky person that gets to see you undress at the end of the day. Hopefully the image above illustrates how truly awful braces and belt together look.
8 Keep Patterns To A Minimum
The most basic rule of pattern matching for men is don’t. If you are wearing a suit or jacket with stripes, wear a solid shirt and solid tie. This will look good one hundred percent of the time. If your jacket is plain, wear a patterned tie with a solid shirt or a patterned shirt with a solid tie. The gentleman above demonstrates a perfect combination: solid jacket, solid shirt, patterned tie, and pocket square which doesn’t match the tie (see item 6). This is also a good time to suggest that you don’t combine more than three colors at a time. Again in the example again you see blue, gray, and tan. Anything more would look cluttered.
However, once you get the hang of it or if you are particularly adventurous, you can move to the next level of stylishness by breaking this rule entirely and mixing patterns. But remember the golden rule: don’t combine patterns of the same type unless they are extremely different in size (wide striped tie with pin striped suit is fine). So a fine striped suit with a herringbone shirt and plaid tie can look really great and show you have a good eye for detail. And never wear ties with cartoons, words, or funny pictures on them.
7 Formal Shoes
Formal shoes have leather soles (except in some cases where they have a rubber Dainite sole to cope with snowy weather). There is no other type of formal shoe. And formal shoes are certainly not made by children in Asia. Formal shoes should also not have elongated toes or squared off toes. They should have a natural rounded shape. And now to complicate things a bit. There are two basic types of formal men’s shoes. Oxfords are worn with a suit and the flaps that hold the laces are seamlessly joined to the rest of the shoe upper, and derbys, also known as bluchers are worn with mismatched jackets and trousers and the flaps that hold the laces are separate pieces of leather attached to the shoe upper.
6 Pocket Square
These aren’t particularly common nowadays but some men do still wear them. The rule with pocket squares is simple: it shouldn’t be the same fabric as your tie and shouldn’t match the color too closely in case it looks like it is a set. Of course the easiest thing to do is just wear a white pocket square which is always fine (linen—not silk), but if you do want something more interesting, pick the second most dominant color in your tie and let that be the dominant color in your pocket square. If your pocket square matches your tie (except in the very formal case of wearing a tails suit) you will look like you stepped out of a bad 1980s wedding party.
5 Undershirts
Your undershirts, like your underwear, should never be visible. That means either going without an undershirt or wearing a vest if you want to wear a business shirt with the top buttons undone. It is a very commonly seen error (particularly with American men) to have a tee-shirt visible above the top of an unbuttoned business shirt. It looks lazy and careless and is nearly as bad as walking around with your trousers half way down your butt exposing your underwear. The photo above illustrates how terrible it looks when your undershirt is visible.
4 Do Up Your Tie
Never wear a loosened tie like you see in the movies. That is for when you get home half drunk from a night out or when you start in a Hollywood blockbuster. And you must always button your top button when you wear a tie otherwise it looks like your clothes don’t fit and you can’t button your shirt. The other rule for ties is that the tip of the tie should hang at least half way down your belt buckle (or the location the belt buckle would be if you are wearing braces). The gentleman in the photo above is following all the rules on this list (at least the parts we can see!)
3 Socks
American and British men have had different rules for socks over the years but the most traditional rule is to match your socks to your pants. On the other hand, it is also nice to match your socks to one of the colors in your tie or another part of your clothes. Or you can be really outrageous and wear zany colored socks (after all, they aren’t exposed often). This is seen more often in the UK than the US and it can be a nice way to be a little playful when you need to be very conservative in your dress style. But don’t wear socks with cartoons or pictures on them – stick with solids, or patterns. Also, the ideal men’s socks pull up to just below the knee (hence the extra-long appearance of the socks in the above photo), preventing any skin from showing when you sit down or bend over.
2 Designer Labels
Designer labels are almost always a rip-off. They are usually overpriced for the quality and fashion forward to ensure that you will be a repeat customer. Photos of you wearing the latest Hugo Boss or Armani suit (cheap rubbish at luxury prices) will look dated in a few years . . . think 1970s wide lapels. The current trend is for skinny lapels. Avoid the trend and get a good quality moderately priced suit or jacket with medium width lapels and two or three buttons at most. That is a timeless style that will enable you to keep wearing the suit until it has holes in it (and then you should get a tailor to fix the holes rather than buying a new suit, but that’s for a whole other list!)
However, if you really must buy designer labels (and can afford them), the only labels in suits you should consider are Kiton, Isaia, Brioni and a few other Italian brands. Everything else (including Tom Ford, which is amazing quality but modern design) is going to date. However, suits from those brands can range in price up to $70,000 (that’s not a typo). Pictured above is menswear by Kiton and if you want proof of the timelessness of these brands, check out Pierce Brosnan in Goldeneye in which he dons Brioni suits throughout.
1 Your Only Suit
If you only ever own one suit, it should be gray (preferably dark gray). A dark gray suit is perfect for weddings, interviews, funerals, the theatre, and everything in between. If you are rich enough to be able to buy more than one, you can then add shades of blue, and brown. And if you are really rich, get a black suit . . . but only wear it to a funeral. Black is a funereal color and it is not correct for a business suit. And don’t forget that a suit or jacket should always be buttoned up when you are standing and optionally unbuttoned when you are sitting. And the last suit rule is that if it has three buttons, leave the bottom button undone as suit jackets are designed to be worn that way. Pictured above is Pierce Brosnan in a Brioni charcoal suit twenty-two years ago! He could wear it today and it would look perfectly modern and fresh.
+ Competition
It has been far too long since we ran a competition and because I am so fanatical about good menswear this list seemed like a perfect opportunity to launch one. To enter you just need to post a comment on this list that relates to menswear and at the end of the day I will select the five commenters with the highest number of upvotes to win one of five pocket squares from Drake’s of London, each valued up to $100 USD. You can browse the selection of pocket squares here (if you win you can pick the one you want). Drakes makes the most amazing clothes and they are my first choice for pocket squares (some of which are pictured above).
This competition is open to all countries and both genders. So, get commenting and good luck!