1. A Really Good Pair of Jeans
Doesn’t matter if you wear jeans every day or if you only own the one pair — own a really good pair. What makes a really good pair of jeans? They should be sturdy, comfortable, and versatile. You want jeans that aren’t a statement all on their own. The goal is to have pants that can be dressed up, dressed down; whatever — they should look equally good paired with a plain white T-shirt and with a sharp-cut suit jacket. Or with both at the same time.
2. A Plain White Dress Shirt
Like the good pair of jeans, this isn’t the most exciting garment in the world. It’s almost generic. But it’s also worth having. A plain white dress shirt can be worn with anything. It’s a must-have if you’re wearing a suit, at least for your most formal business settings. A lightlypatterned dress shirt is fine for most workplaces, but when you need to look like serious business, pure white is your gold standard. On the opposite end of the spectrum, the same shirt looks just fine with a beat-up pair of jeans (it’s a little cowboy, but there’s nothing wrong with that). And it’ll work fine with cords, chinos, blazers, sports jackets — whatever. You can even untuck it and roll the sleeves and make it work with shorts in the summer.
3. A Pair of Dark Leather Shoes
Never underestimate the improvement a good pair of shoes makes on an outfit. If you can’t bring yourself to be the kind of man that owns many pairs of shoes, make sure to have at least one pair of dark leather ones in your collection. The ideal style can vary a little depending on your needs. For strict business dress, plain black oxfords are the only option. Men who don’t have much call for business dress can get away with a more relaxed black shoe, or even a dark brown one. The point is to own a nice pair. They may feel dressy at first, especially for men who are used to gym shoes or synthetic-material work boots, but rest assured that leather shoes dress down just fine when you pair them with jeans and a relaxed belt. As with the other must-have items, it’s worth your while to invest up front here. Get a really good pair that fits like a glove. With occasional cleaning and polishing, it’ll last you for years.
4. A Navy Blazer
A stylish man will probably own half a dozen jackets or more. But every man should own a navy blazer. Blazers are a versatile middle ground. They’re a little dressier than casual sports jackets, but not as dressy as a suit. That makes them a great default any time you want to look “nice” but aren’t sure what statement to make beyond that. You can go to church in a blazer, you can go on a date in one; you can even appear on TV in one. Keep your first blazer simple and elegant. The navy blue fabric color is a must; the traditional metallic buttons are optional, and can be replaced with darkcolored leather, horn, or mother-of-pearl if you prefer a lower contrast look.
5. Gray Wool Trousers
Of all the items on this list, gray wool trousers are probably owned by the smallest number of men. That’s unfortunate, since they’re the ideal jeans alternative for most settings. When you want to look dressier than denim can manage, you have lots of options, but few are as simple, practical, and versatile as gray wool. The gray can vary from light to medium to charcoal dark, and the wool can be flannel, worsted, or even a textured weave like herringbone. The requirements here aren’t too specific, beyond “wool” and “gray” — and, of course, a good fit.
Get a pair if you don’t already own one. You may feel a little overdressed in them the first few times out, but you’ll quickly realize that they can be worn even in very casual settings for a look that’s not out of place — but that is a little nicer than all the jeans-wearing men around you.