SWT: 1. Update your wardrobe - By update, we don't mean throw everything out and splurge on getting new clothes - no. Just try to wear clothes that fit you well and stick to timeless fashions, rather than trying too hard to go with the latest fashions.
MP: 1. (Try to ) Update your wardrobe (at least every decade) - and stick to the classic must haves like the non-iron dress shirts from J. Crew or Banana, along with your favorite classic pair of jeans. If you have a difficult time combining your clothing items, there are services you can tap into (i.e. TruckClub - where individual stylists (usually semi hot chics) will help you look semi handsome as long as you (spend money to) buy their clothes.
SWT: 2. Get a few timeless items that look rich - Spending a little extra is not a bad idea if you do it well. For example, if you buy a simple yet a brand name black sweater, it could go with many outfits, making them all look expensive.
MP: 2. Get a few timeless items that look rich (and that you actually look good in). Looking "rich" can have it's benefits, but lets be "REAL"... you don't need gold digging chics chasing you... you're waaay more mature than that?!
SWT: 3. Never overdo any outfit - Nothing takes away the stylish factor like trying too hard. Remember the golden rule, simplicity is the best policy.
MP: 3. Never overdo any outfit (unless it's your socks).
SWT: 4. Focus on your hair - For everyday styles, braids and loose waves look great, but even for formal occasions, don't let too much effort show. Try a bun, they are classy and stylish.
MP: 4. Focus on your hair (if you have any to begin with, by all means set it free…).
SWT: 5. Makeup is essential not a lifesaver - Don't use makeup like you need to - use it like you want to. Keep it neutral, simple, let your naturalness show through.
MP: 5. Clothing is essential, not optional.
SWT: 6. Choose a look that you are comfortable with and stick to it - If people regularly see you in a certain type of look, it will automatically make you seem stylish, like you always look good without trying.
MP: 6. Choose a look that you are comfortable with - Steve Jobs owned a lot of mock neck shirts and Levi jeans.
SWT: 7. Confidence = Style - There is nothing wrong with being confident about looking good, let it show.
MP: 7. Confidence = you've got ManPossible... what else do you need to boost your confidence?