Suiting Up: The Basics

Fashion is temporary, style is timeless.

If you’re not already wearing suits on a regular basis, it’s time to start. Children wear shorts, ballcaps, jeans, sneakers, hoodies, and t-shirts. Men wear suits, blazers, trousers, loafers, oxfords, button down shirts, and polos. Of course these aren’t absolutes, but certainly you must agree that the typical slob goes out in public these days dressed like a little boy instead of a man.

Obviously there are all kinds of exceptions, and allowances for personal tastes, but every man would do well to learn and follow the basic rules of timeless style.

There is a reason why most men in television programs and films have traditionally been portrayed in suits and ties, even when they would appear overdressed in real life. It’s because they naturally command more respect and admiration, from both sexes, when dressed like a serious adult. If you fail to see the utility in commanding more respect from those around you, you might have issues a suit can’t fix.


The first rule is to ignore fashion and develop true style. Style is classic and timeless. Style is traditional, because the same things that looked good 100 years ago still look good today. If your great-grandfather would have been proud to be seen in your outfit, you’re probably doing it right.

Alright let’s get down to brass tacks. Here are the main rules that should be followed when you’re first getting into dressing like a man. Most guys with white collar jobs will already know all of this stuff. We’re only going to look at the basics here, to lay the groundwork for more advanced articles.

  • Stick with solid navy or solid charcoal for your first suits.
  • Avoid checks, plaids, stripes, herringbone, bright colors, or anything unusual until you are highly experienced in the sartorial arts.
  • Never buy a suit with polyester fibers. Stick with 100% virgin wool. Rayon blends, cashmere, and linen are great but not before you have a closet full of 100% wool.
  • It’s better to buy just one well-made suit from a reputable maker, than to buy three or four inferior suits.
  • Look for full canvas or half canvas construction. Avoid fused/glued suits. This probably won’t be on the label, so ask. If your salesman doesn’t know what you’re talking about, be weary. Their suits are probably held together with Chinese glue.
  • Plan on having your new suit tailored to fit, and reserve some budget for that, unless of course you are getting it custom made.
  • Avoid any suit that retails for less than $500 USD. Never buy Kenneth Cole Reaction. or other downmarket lines from higher end brands.
  • Most suits sold at Macy’s and Men’s Wearhouse are garbage. If you must buy from a national retailer go to Nordstrom. Good deals can be found at Nordstrom Rack if you know what you are looking for and don’t just grab whatever is cheap.
  • Don’t try to get too fancy – stick with a single-breasted jacket, standard notch lapel, single or double vented, with flat-front trousers and no cuffs.
  • Avoid slim cut jackets or skinny trousers unless you are seriously underweight – in which case I’d recommend spending six month bulking and lifting weights before your purchase.
  • Likewise, if you are overweight, focus on getting yourself down to the weight you want to be before you go suit shopping. Buying a high-quality suit built to accommodate your unsightly girth will only serve as another demotivator when it comes to getting in shape, and it’s unlikely to make you look any better than if you were in Dockers and a dress shirt.
  • Work with a tailor in person to establish the right sizing and fit. Sleeve length should cover half of your wristwatch with arms hanging at your sides. Trouser length should barely touch the ground at your heel. Trousers should never be too tight around the thighs and groin. Chest and shoulders shouldn’t bunch up or become tight when holding your arms outstretched.
  • Buy high-quality leather belt and shoes, of matching color. Preferably from the same maker, such as Allen Edmonds. Avoid flashy, oversized, or intricately designed belt buckles. They look really cheesy in most cases.
  • Buy socks that match your trouser color. If you want to add flair they can have a secondary or even tertiary colors that are bright and attention-grabbing, but the primary color should be close to an exact match with your trousers.
  • Start with solid color dress shirts of high quality cotton. No need to venture beyond solid white until you have mastered your personal style. Shirts should be fitted with the same care as suit jackets. Sleeves should stick out around a half inch beneath the cuff of your jacket. Avoid big billowy shirts designed for the typical fat slob. Get slim or athletic fit if you have a good physique to pull it off.
  • Get yourself a nice mechanical or self-winding wristwatch. It’s the ultimate accessory for men. For the love of god don’t wear anything digital, or an Apple Watch, or big clunky metal watchbands. Avoid brands from clothing designers like Gucci or D&G. Get the kind that has a sweeping second hand, that must be wound. No quartz. Go for an understated leather band that matches the color of your belt and shoes. Black and brown are obviously your two choices here, and it’s a good idea to get both so you can change them out to match your black and brown shoes…unless you can afford several high-quality watches.

Here are the top mistakes I see noobs making when they try to “dress up”. Unfortunately these errors are likely to make you the target of mockery among the moneyed classes, and may even cost you a job opportunity with a discerning interviewer.

Bad fit. This stands out like a sore thumb. Sleeves or pants too long, too short, too tight around the belly, etc. Invest in tailoring or don’t wear a suit, period.

It’s easy to go off the rails when you’re trying too hard.

Unnecessary flair. Plaid jackets, weird colors, pocket squares,  wacky ties, crazy belt buckles, hats, cuff links, tie bars, mandarin collars, etc. Most of these things are just fine, but only after you’ve mastered the basics and fully understand the underlying fundamentals. You need to learn your color wheel before you can paint a masterpiece. And besides, style is always best when slightly understated. You don’t want to look like a pimp do you?

Mismatched leather. Your watch band, wallet, belt, and shoes should all be very close to the same color tone of leather. If any of these are mismatched it will downgrade your style substantially.

Wrong color socks. Most obviously, white athletic socks are the death knell for anything but athletic clothing. But there are several other ways your sock choice can go sideways. Just match them to your trousers and you’ll be fine.

Bad shoes. The shoes are just as important as the suit, and neither should be cheap or tacky. Scuffed shoes look terrible. Always polish them up to a nice shine and get rid of scuff marks. Square toes are dumb-looking in most cases. And the cheaper they are, the more they will look like cheap shoes. You will not find stylish, well-made dress shoes in places like Ross Dress for Less, Marshalls, Shoe Pavilion or JC Penney.

Black suits. Sure, the dudes in Resorvoir Dogs looked badass in their black suits, but unfortunately you will not. You’re more likely to look like a waiter, or, well, a noob. If you’re not attending a funeral or a black tie event, steer clear of black suits and go for charcoal instead.

Stupid watches. As mentioned above, you are just making yourself look like a dork if you are wearing Apple watches, LCD watches, Casio, Timex, or watches with a big designer logo on the face. The more understated the better. Be a man and get yourself an Omega or a Patek. And if I see you with a Rolex, I will laugh at you. It’s probably a fake anyway.

Omega Seamaster – the gentleman’s choice

Alright gents, hope this article helps you when you’re just starting to put together your adult wardrobe or preparing for an important job interview. Let me know your thoughts in the comments.

Leave a comment

Please Login to comment
Notify of