Was Woodrow Wilson progressive?
In regard to foreign policy, yes; domestically, not so much.
Wilson's legacy is highly regarded in Western Europe (there is an avenue named after him in Paris), due to his Fourteen Points—a plan for peace issued to negotiate the end of the First World War, which had a devastating impact on the continent.
In sum, Wilson's Fourteen Points encouraged frank and open diplomacy, free navigation of the seas in peace or wartime (the sinking of the passenger liner, the Lusitania, supposedly precipitated the American entry into the war), equal trade, the establishment and re-establishment of sovereign nations, and the evacuation of occupied territories in Belgium, France, and Russia. The Tenth Point helped to break up the empire of Austria-Hungary by allowing peoples within its crumbling border to determine their own nationhood.
The Fourteen Points is an extraordinary piece of diplomatic action. Its recognition of free trade and national sovereignty—all under the aegis of good will and mutual respect—makes it a diplomatic standard bearer.
At home, Wilson was less respectful and forward-thinking. Domestically, he is well-known for his racist attitude and discriminatory policies toward black people. For example, he favored the segregation of black federal employees, believing it to be more "beneficial." He failed to be receptive to the concerns of NAACP leaders, such as Ida B. Wells and William Monroe Trotter, who visited the White House. Wilson praised D.W. Griffith's 1915 film The Birth of a Nation and had a private screening at the White House. All of this occurred during a period in which the number of lynchings of black people was especially high. Deadly race riots broke out in cities throughout the United States in the summer of 1919, which, due to its extensive bloodshed, was nicknamed "Red Summer." Wilson, a Virginian with nostalgia for the Confederacy, was indifferent.
In regard to women's suffrage, he was a little better. Initially, he ignored the white women who protested for days outside of the White House and only became responsive when he learned that they were arrested and jailed. While imprisoned, the suffragists went on a hunger strike and were force-fed by their jailers. The thought of these women living under such conditions swayed Wilson who, on September 30, 1918, decided to speak before Congress in favor of the passage of the Nineteenth Amendment.