Creating multiple windows login on a single databae
Test your Windows logins with SQL Server Management Studio

At a very basic level Let's test your logins with SQL Server Management Studio. You need to first log into the Windows machine with the login you created, and then login to SQL Server Management Studio with that same Windows login. 

Once you've logged in through Windows, open SQL Server Management Studio and register SQL Server via the connect button Shown in Figure A. Here you register your SQL Server specifically for that login. Next, in Figure B you can connect specifically to SQL Server with the Windows login. The Connect To Server dialog box will automatically have the Windows login information provided that you've selected Windows authentication--but you may need to type the SQL Server name correctly.

Figure A: Register SQL Server for your Windows login



Figure B: Test Windows authentication on SQL Server with your Windows login



p.s. With SQL logins, you're saved the hassle of logging in and out of Windows to test those logins. But I guess you could take a shortcut, hold down the shift key and right-click the SQL Server Studio and select Run as different user--to shortcut the Windows login/logout process. 

I've noticed that Run as different user selectively shows up in some places and not in others. For example, in Windows Server 2012's search menu, shift-right clicking SQL Server Studio will not reveal this command, but if I pin Studio to my task bar and shift-right click it's there.

Your question is kind of general (as there are numerous ways to login to SQL Server with Windows authentication)--I hope this explanation is a value to you and is what you needed.