Dressing with individuality and making bold choices. Plus, is it OK to mix and match your suits?.

This week, we are trying to step out of our comfort zone. Albeit rather tentatively. One question concerns challenging ourselves with a bold style choice, rather than sticking to a safe one. Another is from a gentleman who is unsure whether he can break up his suit and mix and match his jacket and trousers. (Spoiler: he needn’t be so cautious.) The third question is about finding your own style. What a nervy bunch you all are.

Keep your emails coming to asky@mrporter.com. And keep an eye on our social media feeds and ask us anything you like on Twitter, Facebook and Instagram. Until next week.

Go with the safe choice or challenge yourself with a bolder one?

From @gustavemilloft via Instagram

I suspect, Mr Milloft, that you have asked this question because you would quite like to try something bolder, but aren’t entirely convinced it will work. This is a case of risk assessment and confidence. How far can I push it before I start to look silly? If you find yourself wanting to be a little more adventurous with your clothing, but the idea of wearing anything other than black, white and navy frightens you, it’s probably not the best idea to start rocking a royal-blue poplin boiler suit, although Engineered Garments does just the thing if you find you have the chutzpah to carry it off.

In other words, don’t run before you can walk, but don’t let that stop you from experimenting here and there. With clothes as with music, it’s judicious to learn the classical basics before you start on the jazz. Those blues scales will prove tricky if you don’t have your arpeggios down first. Take what you are comfortable with and push your sartorial comfort zone in subtler ways by building out from there. A camp-collar shirt, for instance, can add a little élan to a summer look and some wide-legged trousers will give an outfit a contemporary edge. If you’re afraid of colour, add some by way of your footwear, or with a belt or socks. It’s a good idea to have a few go-to brands you can rely on. President’s makes summery clothes that fall on the right side of sophisticated, while Copenhagen-based NN07 does a great selection of bright colours that can add some pep to an otherwise safe look.

In the end, dressing well is not about being safe or bold, or even about challenging yourself. It’s simply a matter of enjoyment. If you find you like it, give it a shot.

What is the best way to develop a style that is unique to you and reflects your self-image?

@austinkrader via Instagram

This is a tricky question, Mr Krader, because we don’t know what image you wish to project, especially because your Instagram account is private, so we were unable to do any sleuthing. However, we can offer some suitable advice without stalking you on social media if we summarise your question thus: how do I develop a style that is personal to me?

As with most things in the world of clothing, subtlety is your friend. Listing your personality traits, likes and dislikes, and then buying clothes accordingly will not end well. No one likes a try-hard. Build your style organically, and only consider pieces that feel right. Seasonal trends, for example, can cause people to purchase clothes they are not comfortable in simply because they are popular. Do not do this. Belt bags don’t work for everyone. Neither do gargantuan Givenchy shirts with dragons emblazoned on them. When you’re thinking about a purchase, if the answer to the question “do I like the look of this and do I think I will look good in this?” is not a resounding “yes”, move on and consider for something else.

Where to start? Your question suggests you might be looking to build from the ground up. Scroll through our Essentials edit and see which pieces take your fancy. Then look at different brands to find out which designers make your preferred pieces. For example, if you’re a chinos man, do you like Incotex’s approach or AMI’s? In the market for a floral shirt? Do you want to go loud or keep it more subdued? Burberry or Saint Laurent? It depends on how much of an extrovert you are.

Finally, you may be on the hunt for things that will make your look truly “unique”, as you referenced in your question, items that will elicit interest and conversation. Perhaps it’s about investing in brands with an esteemed history, such as John Lobb. Maybe you want a rare accessory that few of your contemporaries will have (Luis Morais is your brand). Or you could decide that you’re into a niche and nerdy production technique, such as the traditional dyeing process used by Blue Blue Japan.

Can you break up a suit, ie, wear the jacket with trousers that are a different colour?

@theangrypatissier via Instagram

The short answer to this question, Angry Patissier, is yes. Obviously, you should initially buy a suit – by which we mean matching trousers and jacket – for its intended purpose. It is the thing one should wear to formal occasions. It may be what you decide to wear for your wedding. Or perhaps you need one for work. However, it does not need to remain a singular entity. Unless we are talking about a suit that you want to keep pristine and wear only for special occasions, we would actively encourage you to mix and match your jacket and trousers as you see fit. You can, for example, dress your jacket down with a pair of jeans. Just watch out for colours that don’t work well together. We would advise against wearing blue jeans with a smart blue jacket, for example. Similarly, feel free to partner smart suit trousers with something more casual, such as a tucked-in white T-shirt, or a short-sleeved shirt and sweater, up top.

Your question suggests you are wondering whether you can break up your suit with a different pair of trousers, whether they be chinos or a wool pair, and still look smart. Again, the answer is yes. But, again, you need to consider clashing colours. Suits come in all sorts of hues these days, so use your intuition. Stick to charcoals, browns, blues and dark greys and you should be fine. If your jacket has a pattern – a check, for example – make sure there isn’t too much going on downstairs. Err on the side of caution and go for plain trousers or something with a subtler pattern. Use your common sense. If you think it clashes, everyone else will, too.

Fit is also an important factor. If your jacket is on the slim side, wide-legged wool trousers should be avoided. And if you’ve got yourself a wide-shouldered, double-breasted jacket, don’t be the guy who pairs it with spray-on black jeans. You want trousers that have a similar fit to your jacket.