If the fabric includes linen, it will be nearly impossible to achieve a cotton (or synthetic) outcome from ironing as linen has a natural wrinkle to it. But the suggestions made here are good ones to maximize the outcome.

That's a great looking watch. I wear a "smart" watch - a Garmin Fenix 6, with a metal bracelet, which is quite similar. I think the general concuss that "you shouldn't wear a smart watch" is probably more accurately stated as: wearing an Apple Watch with a rubber band is less ideal than a traditional watch. I think as you move away from the Apple Watch and rubber, toward something like what you and I have, the lines get blurry.

I have a fundamental issue with Chelsea boots being called “masculine”. They were originally women’s boots (as AC did a great job explaining in one of his videos, they were made for Queen Victoria and weren’t very popular for men until the rock-and-roll era of the 1960’s) and are considered feminine by women (here’s a great video: https://youtu.be/_M8juAANqQc?si=OZV65lfwh49xuZfU). There’s nothing wrong with being feminine, but I think it’s important to call it out. There are exceptions: Blundstones and Redwings Chelsea come to mind, but those are extremely casual and thus lose the versatility to be dressed up or down. So I’d reluctantly say keep white sneakers, presuming that they are high-quality, leather sneakers properly maintained to look fresh. They are versatile mainly because they are neutral, unless you’re a man who wears formal wear every day (which I don’t, although I realize this community skews toward those who do, but I think the vast majority of men live and work in setting for which elevated casual is far more appropriate than formal wear) Write-in option: a pair of lace-up service boots. As versatile as a Chelsea, but they actually are masculine. The right pair (example: Thursday’s Vanguard) can be dressed up and worn casually, spanning more range than either the Chelsea or the white sneaker.

Here’s what I would prioritize in this order: 1. Lose weight and build a good physique 2. Get a good grooming (hair, skin, teeth, nails) routine 3. Tailor your existing clothes to fit well 4. Upgrade shoes 5. Upgrade jackets 6. Shirts and pants 7. Fragrance 8. Whatever else interests you: watches, jewelry, hats, erc

I agree navy chinos will look great. I had the same reaction the “it doesn’t look right” but I think it’s just because it’s different. For a more casual look, light or medium stone wash denim. Also, in the warmer months, linen pants in olive or blue.