Men new to tailoring tend to focus on surface-level choices: a bold colour, a contrasting buttonhole, a distinctive lapel. However, fit and silhouette are the foundation of any good outfit and no amount of styling can save a bad suit. A well-cut navy worsted will always look better than a poorly tailored show pony.

A well-tailored suit jacket should always hug your neck, even as you move. If the collar lifts or gaps, the problem is likely architectural – an incorrect shoulder slope, excess tension across the chest or a misalignment between the garment and your posture. These flaws are rarely correctable after the fact. If the collar doesn’t stay seated on your neck, it is best to move on.

Next, check the jacket’s balance, which is tailor vernacular for how it hangs from your shoulders. When viewed from the side, a jacket’s hem should fall evenly from front to back, like a scale in equilibrium. A slight dip in front is fine, but if the front hem rides higher than the back, the whole jacket will look like it’s shrugging away from you. Once again, move on.

Subtle distortions can also offer clues. A sleeve-head divot – a puckering that appears just below the shoulder seam – may indicate that a jacket is too tight across the back. Lapels that bow outward suggest chest strain. The coat may need additional room if the waist button pulls into an “X” shape. Lines on trousers, too, reveal issues: flaring hip pockets can suggest tightness across the hips while collapsing fabric beneath the seat often indicates an overly long rise. A well-fitting suit drapes cleanly, creating a flattering silhouette without wrinkling or ripple.

Time matters: start your search early – ideally many months out – so you can try different styles, see what works and, if it needs a tweak here or taper there, you can give your tailor enough runway to make the good suit great.

If you’ve been invited to a wedding, remember that you’re not the main character. Someone is footing the bill for your meal, the venue and possibly your lodging. At a minimum, they’ve invited you to be part of one of the most important days of their lives. Your clothing should reflect a spirit of gratitude.

In most cases, that means leaning toward restraint. A dark suit in navy or grey, worn with a white shirt, dark tie and proper dress shoes, will almost always be appropriate, as it often allows you to blend into the background. This isn’t a failure of imagination, it’s a gesture of respect. Loud outfits or overly casual choices risk pulling focus from the people you’re there to honour.

Some couples want something more creative, some even calling for full-on costuming. If they’ve asked for that, lean in. If your invite spells out a dress code, take it seriously. If it doesn’t, or if the language is vague, ask.

If everything goes well, this will be your only wedding, making this a day worth marking. For most men, black tie is the sharpest they’ll ever look. It’ll also give your wedding a cinematic quality.

For your first black-tie rig, keep it simple. Start with a black dinner jacket – single- or double-breasted – with peak lapels faced in silk or grosgrain. Pair it with matching formal trousers that have a braid running down the side seam. The shirt should be white, with a pleated or marcella front and a turn-down or wing collar (turn-down is more contemporary and easier to get right). A black bow tie is non-negotiable – hand-tied, not pre-tied.

As for shoes, the most traditional choice is a pair of black patent leather pumps with a grosgrain bow. You can also opt for black patent leather Oxfords with flat silk laces, or black velvet Prince Albert slippers for a slightly relaxed touch (it’s your wedding – you’re allowed one indulgence). Just keep them black, clean and worthy of the moment.

And unless you’re wearing a double-breasted jacket, you’ll need a waist covering: either a black formal waistcoat or a cummerbund worn with the pleats facing up. For summer weddings or warm-weather locales, consider the white dinner jacket. Traditionally worn with black trousers, cream dinner jackets are often styled with a shawl collar for a softer, more languid silhouette.

Not every groom wants to invest in formalwear he’ll never wear again, nor does every wedding call for it. If you’re going to splurge on a wedding suit, it’s worth asking: can I wear this again?

A navy or mid-grey suit is the obvious answer. It’s versatile, classic and works for nearly everything after the honeymoon. But the risk is that it reads too plainly – too much like officewear. You don’t want to look like you’re about to deliver a quarterly report to your spouse-to-be.

Avoid that by leaning into details that make the suit feel ceremonial. Start with a double-breasted jacket, which can give the outfit some verve. Then, choose a proper wedding tie: something in a black-and-white shepherd’s check, glen plaid or puppy tooth. From a few steps back, these patterns soften into a dignified grey that reads formal, not corporate. A grenadine can also be a very sophisticated choice.

Consider adding a real carnation in your lapel if you want to add a quiet flourish. Not the floppy, pre-pinned kind from a prom corsage set, but a properly prepared boutonniere. A florist can condition and wire a single carnation so it stands tall and clean, with a short stem that sits neatly in your lapel’s boutonniere hole. A white or red carnation is traditional and, when done well, it gives even a simple navy or grey suit the dignity of the occasion.

A linen suit is an obvious choice for a summer beach wedding, particularly in sun-faded shades of tobacco brown, cream, tan, olive and dusty blue. But not all linen is created equal. A heavier weave will rumple more than it wrinkles, which means you’ll look rakish, not dishevelled, by the end of the ceremony.

When purchasing a linen suit, you want to account for linen’s natural qualities. First, since linen doesn’t have the crimp found in animal hair, it doesn’t have that bouncy, stretchy quality natural to wool garments. Thus, be careful of going too slim. If you stretch your arms forward as though you’re hugging someone and feel the back pulling taut, you should size up. Second, remember that the jacket sleeves and trouser legs will accordion once the wrinkles set in. If you hem everything to perfection at the first fitting, you may end up looking like you outgrew your suit by cocktail hour. Build in a little extra length to give the cloth – and yourself – some breathing room.

For an autumn barn wedding, turn to fabrics with texture and weight. Cavalry twill, woollen flannel and even corduroy can all be good choices, so long as the cloth doesn’t feel too casual. Woollen flannel, which has a soft nap, does exceptionally well with patterns. The nap blurs sharp lines, making checks and small-scale motifs more forgiving. Glen plaid, houndstooth and nailhead are especially effective here, helping a traditional grey suit feel more distinct without looking loud.

Before you commit, picture the photos. Not the ones you’ll post tomorrow – the ones you’ll show your kids or look back on when you’re grey. Do the images reflect what you wanted to communicate? If so, you’ve struck the right tone.