Head­ings present two prob­lems: struc­tural and ty­po­graphic. Cure the struc­tural prob­lem and the ty­po­graphic prob­lem be­comes simpler.

The struc­tural prob­lem is that law­yers of­ten use too many lev­els of head­ings. This leads to in­creas­ingly des­per­ate at­tempts to make them vi­su­ally dis­tinct, usu­ally with in­ju­di­cious com­bi­na­tions of bold or italic, un­der­lin­ing, point size, all caps, and first-line in­dents. The re­sult is train­wrecks like this:

iv.) The De­fen­dant Has
Suf­fi­cient Min­i­mum Con-
tacts with California.

Head­ings are sign­posts for read­ers that re­veal the struc­ture of your ar­gu­ment. Note that I didn’t say the struc­ture of your doc­u­ment. Head­ings that an­nounce every topic, subtopic, mini­topic, and mi­cro­topic are ex­haust­ing. If you write from an out­line, that can be a good start­ing point for your head­ings, but don’t stop there—sim­plify it further.

Limit your­self to three lev­els of head­ings. Two is bet­ter. Read­ers should be able to ori­ent them­selves from the head­ings. With more than three lev­els, that task be­comes hope­lessly con­fus­ing. You may know your ar­gu­ment in­side out, but no one else does (or will).

Once you’ve cured the struc­tural prob­lem, work within these ty­po­graphic parameters:

1. Don’t use all caps. If your head­ings are full sen­tences, then they’re too long for caps. And Al­ways Avoid Ti­tle Case, Be­cause Your Head­ings Aren’t Titles.

2. Don’t un­der­line. Why? Re­view un­der­lin­ing.

3. Don’t cen­ter, sub­ject to the ex­cep­tions in cen­tered text.

4. The best way to em­pha­size a head­ing is by putting space above and be­low, be­cause it’s both sub­tle and effective.

5. Use bold, not italic. For head­ings, bold is eas­ier to read than italic and stands out bet­ter on the page. And since the choice is bold or italic—not both—you should pre­fer bold. But even then, it’s an op­tion, not a re­quire­ment. Non-bold head­ings work too.

6. It’s fine to make the point size big­ger, but just a lit­tle. Use the small­est in­cre­ment nec­es­sary to make a vis­i­ble dif­fer­ence. If your text is set in 12 point, you needn’t go up to 14 or 15 point. Try a smaller in­crease—to 12.5 or 13 point.

7. Only use two lev­els of in­dent­ing, even if you use more than two lev­els of head­ings. Some writ­ers like to in­dent every head­ing a lit­tle far­ther. Bad idea. It ends up look­ing ran­dom and messy.

8. Sup­press hy­phen­ation in head­ings, and use the keep lines to­gether and keep with next para­graph op­tions to pre­vent head­ings from break­ing awkwardly.

9. See hi­er­ar­chi­cal head­ings for a con­trar­ian sug­ges­tion about how to num­ber headings.