Many years ago, when I decided it was high time for me to look like a respectable adult, I set out to build a new wardrobe. First on the list was a navy blazer. I found an incredibly handsome one at high-end store, but it was outside of my budget. I hemmed and hawed, and considered trying to find a cheaper alternative, but in the end, decided to just save up for the one I really wanted.

Ten years later, I’m still wearing that same jacket. If you factor in cost-per-wear, this probably cost me less than if I settled for something “cheaper.” I now work on a simple principle: it’s better to purchase what you truly want and own it for a long time, than go through cycles of buying things that are never quite right. Of course, nice things are often expensive, so it’s good to know which pieces are truly worth investing in. Here are ten suggestions:

1. The navy blazer: I’ve never met a man who couldn’t use a good navy blazer. Whether worn with rolled up chinos on a boat or with grey wool trousers at work, a navy blazer can smarten a man’s look in just about any environment. Pick something with a textured wool fabric so that it doesn’t get mistaken for an orphaned suit jacket.
2. A brown tweed: After a blazer, the next best sport coat is the brown tweed. Something like a dark brown herringbone can be worn with great success in the fall and winter seasons. Stick to something soft shouldered so that it doesn’t look too stiff.
3. A pair of straight-cut, dark blue jeans: For weekends, nothing beats a pair of dark blue jeans. In some circles, you can even wear these with dark blue jeans for a casual-smart look. Invest in a pair made from high-quality raw denim, so that it will look better, not worse, with age.
4. A pair of trim khaki chinos: Chinos get a bad rap from poorly dressed office workers, but they’re quite versatile for both at-work and at-home use. If a guy gets a pair that’s cut well – not too slim or too baggy – he can avoid the office-drone associations.
5. Grey wool trousers: For every other situation where a man can’t wear jeans or chinos, there are grey wool pants. Virtually every sport coat will look good with these. Light and mid-grays will be most versatile, as a darker grey, while very sober looking, can be tougher to pair with jackets.
6. A bunch of blue dress shirts: White is of course classic, but sometimes it looks too formal. Best are blue shirts, which can be worn to everything except weddings and funerals. Get these with semi-spread collars and barrel cuffs for the most versatility.
7. A pair of black oxford shoes: I know, men don’t wear suits much anymore and they rarely go to formal events. But what are they supposed to wear when they need to? Sneakers? Get a pair of black oxfords for such occasions.
8. A pair of brown chukka boots: I’ll submit that brown leather chukkas are the most versatile casual shoes for men. They look as great with jeans and a leather jacket as they do with wool trousers and a sport coat. The only thing a guy can’t wear them with are shorts, but most of them don’t look good in those anyway.
9. A navy or grey suit: Again, I know most men don’t need to wear suits, but all of us will need to attend some event at some point that requires one: weddings, funerals, job interviews, New Years’ Eve parties, etc. Keep the details sober so that the suit can look appropriate for all these occasions.
10. One good casual jacket: Last, but not least, a man needs one good casual jacket. It can be a waxed cotton Barbour, a cotton Harrington, a leather bomber, a heavy wool duffle, or just about anything well cut and well made. Something to keep out the chill and make a man look smart when a sport coat is too much.  

Need help finding our Ten Essentials or just need some suggestions? Check out our page on Luvocracy for some inspiration.