Thousands of years after man decided to cover up his body with clothes, you might wonder if it was the wisest decision. It may have been practical to an extent, to protect the bare body from the cold for instance, but beyond that the decision remains open to argument. 

Imagine if we were all still walking around naked. We would have saved so much money, and not have had to make difficult choices during weddings and parties, but there may also not have been class distinctions or judgements based on what you wear. As a bonus, vitamin D deficiencies would have been less prevalent. 

Clothes tend to matter less when you are young. As you get older, and your body changes in shape—usually for the worse—some decisions become important. By the time you are middle-aged, your body is older but your sartorial style has remained in the third year of college, taking a while to catch up. 

Wrong choices at this age can make you look ridiculous. You don’t want to come across as wearing clothes that are “age inappropriate". 

There is that really fine line dividing what constitutes cool and what is utterly preposterous—and the wearer does not always get to decide that. In one of the comic strip stories, when Hobbes puts on Mickey Mouse pants with yellow buttons and thinks he will look cool in them, Calvin believes he looks like an idiot. 

“Maybe I’m new wave," counters Hobbes. “Maybe you’re just stupid," replies the child. 

So here’s the question: you have newly crossed over to middle age, don’t have Hritik Roshan’s body and want to look cool/trendy—is there a successful way of doing that? 

The first set of men who used twigs and leaves to cover their basic bits—were they cool for their generation? Did it depend on the size of the leaf? Was the man who used a tapered leaf, because of some exposure from the sides, considered trendier than the one who used a wide banana leaf and therefore came across as a prude? 

There is no easy answer to this. Quite often, we get our fashion tips from fashion designers, blogs and glossy magazines, but more importantly from people who have access to exclusive designers and use their material. This is mostly artists, public personalities, film stars and sportspeople—our prime minister has set a trend with his short-sleeved kurtas. 

Reams have been written on who is fashionable and who is not, and I have found myself disagreeing quite often. This does not mean I am fashionable by any stretch of imagination. But since having an opinion does not depend on having expertise in the field, I am allowed some leeway. 

I do not find Ranveer Singh fashionable, because he tries too hard to shock. Aamir Khan’s clothes are too tight, Salman Khan has always favoured the “distressed" style, even when it was out of fashion, and Amitabh Bachchan’s suits are too garish, to name a few people. Most sportspeople play it safe, though Virat Kohli is getting better with more confidence (my current favourites, if you must know, are Saif Ali Khan, Rahul Khanna, David Beckham and Idris Elba). 

Remember how many times you have looked at that teenager and rolled your eyes because his jeans are being held together at the knees and his underwear’s elastic band says “mermaid" on it? How do we ensure we are not mocked as well for our clothes? 

After scanning through many magazines at the dentist’s clinic and searching online with “how to not look like a dweeb", here are some tips I have gathered that could be useful: 

1. Tuck in the tummy: The belly is the biggest fashion killer. It makes the legs look thinner, and the shirt buttons too stretched. Lose it—though that’s easier said than done. Or else, just take a deep breath and hold… for the three hours that you are out socializing. 

2. Colours: Don’t wear it just because everyone else is wearing it. In Mumbai, on Sundays, most middle-aged, reasonably well-off men dress in mauve, pink or other pastel shorts with coloured polos and loafers. It’s just how it is, but you don’t have to follow the herd. Wear bright colours, if you like, but balance them with other muted ones—like red pants with a white shirt. 

3. Pants/shorts are more practical: Let’s face it—Mumbai and most other parts of our tropical country are hot. Jeans make you sweaty and sticky. Shorts work better, and if you have ungainly or disproportionate legs, wear cotton/linen pants. In fact, practical offices should allow people to wear shorts that end below the knees to work. 

4. Shirts look better than T-shirts: I know it’s an old habit and saved you the trouble of buttons, but collared Ts, polos and shirts are more dignified than round-neck ones. 

5. Sizing: I believe slim-fit is in. Fortunately, it’s possible in India to get clothes tailored, so one can get as “slim" as practical. Go bespoke if you can’t find a size. Dad jeans indicate that you are resigned to your fate—even if they are so practical when going for a heavy meal. 

6. Be your age: Torn jeans, baseball cap turned the other way, oversized beanie hats that look like condoms, man buns, T-shirts that say “I am a prime lover"… work for a limited amount of time and age. On an older dude, they are signs that you are still listening to Guns N’ Roses. I notice a MAMIL (middle-aged man in lycra) cycling on the road, squeezed into tights and wonder that surely there must be better fitness clothes as well. 

7. Avoid athletic wear outside of, well, athletic activities. Synthetic Adidas shorts are bests suited for the gym. 

8. Wear real shoes—and put away keds and sneakers for the weekend, if you must. In India, this is a challenge, because at any point there’s someone waiting to step on your feet—on the streets, in the lift, on public transport etc. You don’t want scuffed shoes, so learn to be more balletic. Chappals look good only with Indian clothes and a pedicure. Floaters smell, in case no one told you. Try sandals instead. 

9. Stay relevant: Donate old clothes to charities that take them and upgrade your wardrobe once in a while. Don’t see it as money spent or wasted, see it as helping someone who needs it. 

10. Don’t take advice from journalists who are not really the standard bearers for elegance and sophistication. 

One of my everlasting memories related to fashion is of James Bond—the epitome of the middle-aged, well-dressed man—in GoldenEye. After running through walls and destroying half of Moscow, Pierce Brosnan peeps out of his military tank and adjusts his tie. 

Finally, how do you know you have reached the age to dress as mentioned above? Fortunately, this is easy in India: some stranger on the street is bound to call you “uncle". 

Letter From... is Mint on Sunday’s antidote to boring editor’s columns. Each week, one of our editors—Sidin Vadukut in London and Arun Janardhan in Mumbai—will send dispatches on places, people and institutions that are worth ruminating about on the weekend. 

Comments are welcome at feedback@livemint.com

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