How to Dress Well 101: How Not to Buy a Suit

When buying a suit, there are a number of common style temptations and mistakes that are worth considering so you know how to avoid them. We’ve all made some of these mistakes, so don’t feel too much shame if any hit a little close to home.

Do I Really Need a New Suit?

If you’re reading this, then, yes, you probably do. But if you’re the type of person who only wears a suit to the occasional wedding or funeral, and takes comfort in the belief that suits offer timeless style, note that that belief comes with some major caveats. It’s certainly possible to look good in a suit that you’ve had for a decade or two — especially if it’s a well-made suit in a dark color — but it really depends on the suit, and it depends on you.

Is it a cheap suit? Don’t expect the fabric or stitching to hold up over time. Synthetics and blended fabrics are least-likely to wear well or last without looking dated. Likewise with thinner fabrics and lighter colors, which will show stains and time’s discoloration more obviously.

Was it a moderately fashion-forward suit? If it was a little interesting when you bought it, it may look a little tacky or dated now. For example, even if you still have a well-made suit from the 80s or 90s, oversized shoulder pads, voluminous pants, and tacky colored polyester are too closely tied to that bygone era to work for anything other than a costume party. If it was very fashion-forward years ago, it may very well look just as interesting still, and you just need to make sure you’re not wearing it so often that you become that guy who seems to only have one suit. When considering your older more interesting looks, a gauche way to discern the line between dreadful and maybe still wearable is how much it cost, though this has more to do with the quality of the fabric and construction than anything else.

And then it’s a matter of how kind the years have been to you. If you’ve lost weight and want to wear a blast from the past, you’re almost guaranteeing that you’ll look like a tent swallowed you. And who among us hasn’t had the experience of pulling on a pair of pants only to discover with dismay that they were made for a much more aerodynamic version of yourself? Either way, tailoring is your friend. If your suit was of decent quality, it’s quick and easy for a tailor to make minor adjustments (if it’s a top-quality suit, like we make at JAKE, you have even more options, since it’s not glued together), such as letting out or taking in the waist or pulling the jacket in at the darts. If you’re just a few pounds too heavy or too light to wear it comfortably, it should cost you less than $50 to make it wearable again. But when it comes to major alterations, odds are you just need to buy a new suit. One test of a good tailor is if they honestly tell you if they can make it work or not, instead of just taking your money and delivering what you’d interpret as subpar work.

If you decide that your wardrobe isn’t really worth trying to salvage, the next step is to educate yourself a little before moving forward with any purchasing. We’re going to save an explanation of what you get at different price points for a different article, and detail here the most common mistakes and other problems we’ve observed.

Jacket sleeves too long. Your jacket cuffs should sit at that bump of bone on the outside of your wrist. This is a little higher than people often think, since they’re mentally comparing the sleeve length of jackets to that of shirts, which people tend to wear a little too long if they buy without sizing them to their jacket.

Shirt sleeves too short. Dress shirts are usually sized three ways: bespoke or made-to-measure; neck size and sleeve length; or sized to small, medium, large, extra-large, perhaps in regular and in slim fit. If the shirt is being made for you, you’re probably fine (unless your tailor is the sort who makes things according to their style, rather than what you want or what’s in style). If you’re buying something based off your neck size and sleeve length, it’s a little easier to match the shirt to your jacket. If you’re buying a shirt that’s pre-sized into a small, medium, etc., it’s a complete crapshoot as to whether it fits your neck, arms, and torso well. Since most people just buy pre-sized shirts off-the-rack, they usually end up with shirt sleeves that are too short? Why? Because it’s impossible to ignore if a shirt is too long and the entire cuff is spilling out of your shirt. So the conservative choice often is to go too short. This results in your shirt sleeve being invisible when you’re wearing your jacket. It doesn’t look bad, exactly, but, once you’re aware of this, it’s an obvious clue that you’re wearing ill-fitted clothes. Most people might not notice that detail, but you will, now. (Sorry!)

Looks cheap. The biggest peril in buying a cheap suit is that it looks like a cheap suit. That sounds like a tautology, but the Men’s Wearhouse advertising has snookered many into thinking that you will, in fact, like the way you look in an intensely cheap suit. But even a $1,000 department store suit will look cheap if you choose poorly (because it is, in fact, a cheap suit manufactured similarly to the Joseph A. Bank two-for-one specials). Does the suit have synthetic fibers mixed with the wool (as opposed to just the lining)? Does it have a shine or a sheen that catches the light? Do you wear your suits so heavily that you need to have them dry-cleaned all the time? Even decent wool will age poorly if you clean it too frequently. Darker colors can help, but avoid black, so you don’t look like you’re on your way to a funeral.

Pleated pants. Pleats are extra fabric gathered at the front of your pants to make them a little more comfortable, at the cost of bankrupting your style. They look terrible, make you look much heavier, and really are worth avoiding. Note that pleats aren’t the same thing as the lines pressed down the front of most suit pants — those simply make the pants look a little more crisp. You’d be hard pressed to find them except at the dowdiest of shops, but even so, beware.

Collar gap. The jacket collar must sit snugly against your shirt collar. If it hikes back, leaving a gap in between, that’s a very poor-fitting suit, even if it otherwise feels great.

The cut is outdated. Mass-market suits are often cut a little more generously, so that they fit a larger swath of people. The better a suit fits more people, the worse it will fit you. There are no average-sized people (really!). Even if you don’t want to wear a slim, fitted suit, you don’t want to look like your suit’s eating you.

The shoulders are too large. It’s easy to go with a jacket that seems to fit well all around, except the shoulders are maybe a little too wide. While it’s possible for a tailor to take out the shoulder pads, reduce them, and reconstruct the shoulders, that really is never worth the time or money. Don’t buy it unless the shoulder pads sit no farther out from where your shoulders drop down into your arms. If they’re too wide, the jacket will wear poorly, especially where the sleeves meet the shoulder construction, and you’ll look worse and worse in it over time.

So what should I buy?

If you’re not sure what to get, stop by JAKE for a free style consultation. You really will, pardon the expression, like the way you look. If you don’t have time, because, say, you just need something to wear tomorrow (and it takes us about three weeks to handcraft one of our suits), just dress like JFK. He popularized the slim, two-button suit, and it’s just as in style today as it was in the 1960s. Note how the shoulders have structure, but appear more natural. The colors are dark and understated, and not too dark. Everything is trim and compact. While it never hurts to have a gorgeous face and tanned skin, this is a look that will make anyone look presidential.