From the top of my head: draw bottom half border on the element and draw top-left and top-right borders on positioned pseudo elements.
/* using 4px border, 1em border radius, 1em padding */
nav ul {
font: medium sans-serif;
text-align: center;
padding: 0;
list-style-type: none;
border-top: 4px solid;
}
nav li {
display: inline-block;
border-left: 4px solid transparent;
border-right: 4px solid transparent;
border-bottom: 4px solid transparent;
border-radius: 0 0 1em 1em;
padding: 0 1em 1em;
position: relative;
top: 1em;
}
nav li:before,
nav li:after {
display: none;
content: "";
position: absolute;
top: -1em;
width: 1em;
height: 1em;
margin-top: -4px;
}
nav li:before {
right: 100%;
border-top: 4px solid;
border-right: 4px solid;
border-top-right-radius: 1em;
}
nav li:after {
left: 100%;
border-top: 4px solid;
border-left: 4px solid;
border-top-left-radius: 1em;
}
nav li:hover {
border-color: initial;
}
nav li:hover:before,
nav li:hover:after {
display: block;
}
<nav>
<ul>
<li>Home</li>
<li>Random</li>
<li>Blog</li>
<li>About us</li>
<li>Contact Us</li>
</ul>
</nav>