For a budget-minded look which will never go out of style and will never be a distraction. In tabulated form. Total outlay: about $350 before tax, shipping, and tailoring. Effective lifetime if you take good care of it: Four years or more.
Retailer: Jos. A. Bank
Minimum Price: $550 list ("Executive" or better)
Discount: At least 60% off list
Pattern: One-color pinstripe
Jacket buttons: Two
Vent: Center or sides
Pants pleats: Two
Cuffed pants: Yes
For Example: This in CHAR STR or this in GREY W/BLUE STR
$20 with coupon
Retailer: Paul Fredrick
Fabric: Pinpoint Oxford
For Example: This in regular or trim (if you wear an M or smaller in t-shirts) fit
Widest Point: No more than 3 1/2"
Base Color: Red
Pattern: Diagonal stripes less than 1/2" wide
For example: This
You'll have to use your judgment on this one. Wear the suit and shirt to the store when you go. If you're not feeling adventurous, the sales staff can help you.
Retailer: Filene's, DSW, any department store...
Style: Cap-toe lace-up
Material: Leather with a sheen (but not patent leather like tuxedo shoes)
Looks like: This but a bit shinier. Ask for a "banker's shoe" in black.
Match it to your shoes as closely as possible. Silver or gold buckle, your choice. 1" wide.
Over-the-calf, gray darker than your suit, any pattern. Like this.