- Gray Suit – The most versatile dress wear in the closet, the gray suit. Make it a medium to dark 100% worsted wool suit from a top brand (Hugo Boss, Calvin Klein, Ralph Lauren, Ben Silver, Brooks Brothers, J Crew), you will get the most use out of this suit. This is the workhorse suit in the wardrobe as it is the most formal suit and the only suit appropriate for weddings, funerals and interviews. This suit can be worn for business, a dinner party or a date. Spend the money on this suit and it will benefit you tremendously. Ideally, get this suit hand made and tailored specifically to you, if only one suit can be bespoke, this is one.
- Navy Blazer – A navy blazer is the uniform of the American male. It can dressed up with a pair of slacks or dressed down with jeans and it will never look out of place. A navy blazer may be most at home with a pair of khakis and a button down shirt, few outfits have more classical appeal. The blazer is as American as apple pie and Pabst Blue Ribbon. Buy one with a modern slim fit, add some gold or brass buttons and you will look like an updated and hip Northeasterner who attended Warton or Harvard. The blue blazer is the best jacket to wear with a dress shirt and tie during the day and a simple t-shirt at night. Make sure it is well made, because you will be wearing it a lot.
- Blue Oxford Shirt – Another quintessential piece of the American wardrobe. The blue oxford shirt has been worn by the best dressed in America for as long as anyone can remember. The Oxford shirt comes in many types, and while I would recommend one of each, at least have a nice one ready when you need it. Dressed up or dressed down the Oxford is shirt for all occasions, except the most formal and somber.
- White Pin-Point Collar Shirt – If the Gray suit is the workhorse of the suits then the white dress shirt is the workhorse of the shirts. This shirt is the most formal of all the dress shirts, appropriate for every occasion, with a tie or not a white dress shirt is never a bad choice. It looks stunning under any suit or alone with jeans during the summer. Many a great wardrobe was compiled with the idiom: “You can never have too many good white shirts”.
- Dark Denim Jeans – Straight or Slim cut clean, simple, dark denim jeans. They are simple, versatile, classic and always popular. Every wardrobe needs one pair of clean dark jeans. Avoid the fancy stitching, flashy pockets or complicated designs, the simpler the jeans the better, in this case minimalism goes a long way. Your closet should have multiple types of jeans, but these should be the first pair you buy.
- Chinos – Every man should own a few pairs of these pants. Whether fixing the car in the garage or worn to work on a more casual day, chinos always look sharp. They are great for a casual coffee date and are the uniform of weekend trips. Chinos are easy to wear, last forever, always look good and are never out of place. They can be worn with a t-shirt, a polo, a button down or a blazer. Match them with dress shoes or Chuck Taylors, chinos always look good. Make sure they are a modern slim fit and a durable material, cause they will be worn until they are frayed and stained and then worn some more.
- Gray V-Neck Sweater – Stick with a light gray V-Neck Sweater, at first, since it is the most universal and will go with any color. The V-Neck can be worn over a shirt and tie for cold days in the winter or over a t-shirt and jeans for a night out. It can be thrown on with shorts for a night at the beach or chinos and a polo for a Sunday brunch. As you expand the wardrobe continue to add more colors of the V-Neck Sweater, but keep them plain to start. Plain sweaters are more useful as they can be matched with anything in the closet, only have you have every color and in cable knit version should you expand to limiting designs like argyle & striped.
- Black Cap-Toe Oxfords – This is most formal shoe you can own. It works with every suit made and is the only option for somber events, interviews and weddings. Keep them polished and in good condition because you will be in these shoes more than your car. Make sure the shoes are Oxfords, not bluchers, have a simple, clean and sleek design. These shoes must have wooden soles that can be replaced and simple laces. These are serious shoes worn with serious suits and should look the part. Also, for the sake of all things stylish make sure they have a rounded toe and are made from real leather. With as wear as these shoes will get, paying a little bit more for them is certainly worth the money.
- Brown Leather Boots – Good quality leather boots will keep your feet dry and be the perfect solution for situations that the shoes make take some wear and tear. Boots only get better with age and become more personalized as they take on wear and care.
- Timepiece – A man needs a timepiece beyond his cell phone. Keep the watch simple, basic and well made. Stick to silver band watches that can be worn with anything from a suit to jeans and a t-shirt.
- Solid Color Neckties – At first only a few solid color ties are all that are needed in the wardrobe, expansion from this point is certainly nice but is not needed until later. One solid blue gabardine tie, one solid dark red wool or silk knit tie and one silk solid black or charcoal gray tie.
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