Before you start:

I cannot say enough about the fit of clothing.  This is far and away the most important factor in any outfit.  Regardless of the price or label, when it comes to clothing… fit is king. 

If fit is king, then quality is queen.  By this I mean that I would rather have one great fitting $25 t-shirt than five $5 ill-fitting tees dug from the bargain bin.  You will be remembered for a great fitting shirt.  You might be remembered for an ill-fitting one, too, but not for the right reasons.  If you happen to find great fitting stuff and it’s on sale then that’s even better.

The idea here is to build a wardrobe of timeless pieces that will last a long time.  For that reason, you may have to spend a little more for some pieces to ensure that you get the best quality and value.  It may take some time, but build a wardrobe that will last.

The list:

Suit

• At least one suit in black, navy, or dark grey is a must.  Fit is key here.  Even if you don’t purchase the most expensive suit good tailoring can make a world of difference.  If you work in a more professional setting have at least 3 suits.  If not, one will ensure that you are prepared for those once or twice a year occasions.
• A sport coat is also a good addition for any wardrobe.  Stick to something classic and timeless that can be thrown on over slacks or jeans.  A navy blazer is a good starting place.

Pants

• Dress pants – at least 3 pair Start with one black, one grey, one brown.
• Casual pants – at least 1 pair
• Khakis / Jeans – at least 1 pair of each.  A good fitting pair of jeans or khakis can be a life saver.  Avoid trends and purchase pairs that fit well and are built to last.  Avoid trendy styling that will be worn out long before your jeans are.
• Shorts – 2 pair A solid or sublte plaid print will get you through most of the summer.

Shirts

• Dress shirts – Have no less than 1 crisp white shirt and one solid blue shirt.  The shade and hue of blue will depend on your preference, but know that the darker the blue, the more casual it reads.
• Business casual shirts – 6 The styling of these can vary.  Mix in some pattern but if they are to be worn to the office, be careful to keep it somewhat professional.
• T-shirts - 3
• Polo shirts - 2 Polo shirts can sometimes work in a business casual setting.  Buy quality.
• Sweaters - 3 One of these should be a good-fitting v-neck.

Shoes

• Sandals - 1 Choose carefully. These quickly go from stylish to silly.
• Sneakers - 1 These are for fashion not function.  You should have a pair of athletic shoes also, but they aren't part of this list.  Think european sneakers here or perhaps a classic pair of converse.
• Dress shoes – one black pair, one brown pair… look for shoes and belts that match so that they can be work together with dress clothes or khakis.
• Boots - 1 winter pair if applicable.

Undergarments

• Socks
• Undershirts
• Underwear

Accessories

• Ties – at least 3 ties, solid medium width is a good place to start if you only have a few.  Beyond that stick with classic patterns such as a diagonal stripe and build from there.
• Belts – one black belt, one brown belt
• Watches – one everyday watch and one dress watch
• Bag - A bad bag can unravel your well-planned look.  Pick one that is simple and timeless.  It doesn't have to be the most expensive, but it shouldn't look like it came free with a magazine subscription either.
• Sunglasses - Protect your eyes and say 'I've arrived.' Choose a style that never goes out of fashion.
• Gloves - leather, not puffy... not puffy.
• Hats - As you see fit, but be careful not to let the hat take over your outfit.
• Scarf - to keep stylishly warm, not the kind that looks like you've been wrestling a blanket.

Outerwear 

• winter coat (if applicable)
• spring jacket