Little joke I thought up Step 1. Buy a pair of jeans. Just one perfect fitting pair. Mine are black, but very dark blue works too. Step 2. Wear the jeans around and buy matching shoes and/or boots depending on climate. Step 3. Buy some mid-price t-shirts that you think you look great in. The right width and length for your body type. Step 4. Go into club Monoco and/or J Crew and get fitted for some Oxford cotton button downs. One in white. One in blue. Make sure it fits. Pick up a white dress shirt while you are at it. Get one with a collar that matches your face. I like small spread collars. Some people have tall necks and need taller collars. Step 5. Only now can you start dressing up. WeR your jeans with OCBD and treat yourself to a navy blazer. Make sure it fits. Not baggy. Not long. Try it on with your shirt tucked into your jeans. Step 6. Go out wearing your blazer and your dress shirt to the pants store. Pick up some dressier pants to replace the jeans. Olive chinos? Grey slacks? Whichever looks right. Wear it. Tuck your shirt into it. Step 7. Now you can shop for a tie or two to complete the outfit. Step 8. Realize you have a few pants, a few shirts, a couple ties, and a couple pairs of shoes to all interchage and one inconspicuous blazer to throw on top. Wear every combination you own with and without the blazer and ties at this point for a full day outside of home. Once you reached that point, start adding one new item a time. Are you needing more shirt variety? More pants? Another tie? Weather too hot? Then you just need more t shirts all along. Weather too cold? If so, get a couple sweaters and another blazer.