Lapel Pins

The left lapel, as you wear the jacket. That is the side with the buttonhole on most suits and blazers, and it is where boutonnieres, poppies and club pins have always gone. Wearing a pin on the right looks odd because the eye expects it on the left. If you wear a pocket square, it also sits on the left, so pin and square share that side at different heights.

Through the buttonhole if your jacket has one, or just below it, centred on the lapel and roughly level with the top of your breast pocket. On a jacket without a buttonhole, push the pin through the lapel at the same spot, about 2–3 cm in from the edge. Keep it above the level of the pocket square, and wear one pin only; two or more starts to look like a uniform.

Yes, and they work well together because they sit at different heights on the same side: the pin on the lapel, the square in the breast pocket below it. Keep the pair balanced by letting one lead. A bold enamel pin pairs with a quiet white or solid square; a patterned silk square pairs with a small, simple pin. Avoid adding a tie bar and a boutonniere as well, or the left side gets crowded.

No, choose one or the other. Both occupy the same buttonhole, and a pin next to a flower looks cluttered. At a wedding, the boutonniere wins for the groom and wedding party. A lapel pin is the better choice when a fresh flower is impractical, for example on a long day, in hot weather or for guests, and enamel or metal flower pins are a durable stand-in for a real buttonhole.

As a guest, yes, a small pin is a nice touch, but skip it if you are a groomsman and the party is wearing boutonnieres. Grooms sometimes choose a metal or enamel pin instead of a fresh flower, especially for destination weddings or a long day, and give matching pins to their groomsmen. Keep it modest in size and pick a metal tone that matches your watch or cufflinks.

Only something small and meaningful, such as a regimental, remembrance or club pin, or a pin that belonged to the deceased. Decorative or novelty pins are out of place. If you are unsure, leave the lapel bare and let a dark suit, white shirt and plain tie do the work. A small pin with meaning is more acceptable at a funeral than a coloured pocket square.

Traditionally no, apart from a boutonniere, or a medal or decoration at a formal function that calls for them. Black tie relies on restraint, and the satin lapel of a dinner jacket shows pin holes easily. If the event is creative black tie and you want one, keep it small, plain and metal, worn in the buttonhole rather than pushed through the satin. A white pocket square is the safer accent.

A stem-style pin leaves a tiny hole, which in wool or tweed closes up when you steam or press the lapel. Silk and satin lapels, and very fine cloth, can show a permanent mark, so use the buttonhole there rather than piercing the fabric. Choose pins with a short stem and a firm clutch back so they do not swing and pull, and avoid moving a pin around the lapel during the day.

Not with ordinary button cuffs; cufflinks need a cuff with two buttonholes and no button, which is a French (double) cuff or a convertible cuff. Convertible cuffs have a button and a second hole, so you can wear them either way. If you like cufflinks, buy shirts with convertible cuffs, or have a tailor add a buttonhole. Forcing cufflinks through a single-button cuff looks wrong and damages the fabric.

Loosely, yes. Keep metals in the same family: silver-toned cufflinks with a steel watch and silver pin, gold-toned with a gold watch. They do not need to be identical, and enamel or stone cufflinks can add colour as long as the metal setting matches. Match colour to the tie or pocket square only lightly, picking up one shade, rather than buying a set. Belt and shoes match each other, not the cufflinks.