Some questions are known as the menswear classics. These are the queries that columns like GQ’s Style Guy, and websites like Permanent Style, get every few weeks – no matter how many times they have been answered.

What should I wear for my wedding? Can I wear brown shoes? How do I tie a bowtie? You know the ones. I’ve answered them all before but I know that a blog is not the easiest thing to browse (trust me, I’m working on it), so below is a selection of my answers – I hope they prove useful.

If anyone has any fresh quries on these topics and they are not covered below, please let me know and I’ll put them in the queue for a ‘reader’s question’ post.

1. What should I wear to a wedding?

Unless the wedding is black tie, which is largely a US affliction, the answer is that you should wear your smartest suit. Probably navy, with black shoes, white shirt and a silver woven tie. It only looks like a business outfit because people don’t wear suits in any other context any more. And with the addition of a crisp white handkerchief and fresh flower, it probably won’t look like any office you know anyway (see picture, a wedding shot from the 1940s).

Alternatively, and fully conscious of the propriety mentioned above, wear casual summer suiting: linen, cotton, buff waistcoats and flowers in the buttonhole. Men don’t get to wear this kind of thing at all today, which is a crying shame, so grab the opportunity of a summer wedding.

Overriding both suggestions is, of course, any guidance you have from the wedding party.

More details in my post here.

2. How do I wear a pocket handkerchief?

Stuff it in. Don’t try and produce a perfect line, or a perfect set of points. Wearing a handkerchief already risks looking affected. Don’t make that a certainty by making its arrangement overwrought.

A silk handkerchief is most easily pushed down into the pocket and then folded over the back. See post here.

A linen handkerchief looks when folded square and then stuffed – the Mad Men look but not so fussy. See post here.

3. I can’t find suits off the peg that fit me. What should I do?

Start by getting them altered. You should be changing the waist of the jacket, the length of the sleeves, the waist of the trousers and the length of the trousers. Doing so will make your suit fit better than those worn by 80% of men out there. Because they don’t bother.

Just make sure the shoulders and neck fit you well, as they are the hardest bits to alter. More details here.

Then, look at made to measure. Although not bespoke, it is a big leap again from ready to wear suits that are altered. Reiss does a good service it has just introduced, and many brands have sprung up that largely do just MTM – Suit Supply, A Suit That Fits, Cad and the Dandy. Plus many brands that say they are offer bespoke mean MTM. Ask if you will have your own paper pattern, preferably cut by the guy measuring you. That defines bespoke.

Post on made to measure here.

4. Can I wear brown shoes?

Yes. They suit more colours of suiting than any other leather and are only inappropriate at some formal occasions or quite formal professions (often the law, for example). Brown leather is also much more satisfying to polish, as you can create your own patina over time.

Just remember to wear a shade of brown that is as dark or darker than your trousers. No tan shoes with navy suits please.

More details here.

5. Can I wear brown in town, white in winter etc?

Yes to all these so-called rules. You can break them, just as long as you know why they are there.

Not wearing brown in town is an old rule telling you to not wear to a business meeting what you wear on the farm. The same applies today, of course, but more importantly it is reminding you to consider the propriety of any occasion when you select your clothes for the day. That’s worth remembering.

My post on this particular rule can be found here.

But I also run a series on these rules – just Google ‘the rules and how to break them’.
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Hi Simon, can you suggest a good MTM brand and/or establishment in the United States.




Who are the pair on the far left of the piccie who look as though they have been smacked on the head by a shovel?


Back-tracking or just becoming more conventional with age?


Excellent post but not sure I totally agree with the no tan shoes with navy suits. I think it can look quite good when done right, for instance when done with Lodgers tan brogues. They are brilliant with dark denim but equally as nice with the right tone navy suit. Also think they go well with grey trousers. Tan adds a bit of a summer touch I guess.

What would you suggest for tan shoes?

most people wear stinky nikes so wearing brown shoes in town is well ok