--pretty=all piped to a pager does not work on Windows

I am trying to use --pretty=all or --pretty=colors to color my output that I am piping to less -r. However, the colors do not show. This could also be solved by adding a paging option for long outputs (like in Git), but I understand that that is much more difficult. I am running this in Git Bash 2.21.0, and also in CMD on Windows piping to more. Neither do the coloring.

$ http --debug --pretty=all https://api.github.com | less -r
HTTPie 1.0.2
Requests 2.22.0
Pygments 2.4.2
Python 3.8.0a1 (tags/v3.8.0a1:e75eeb00b5, Feb  3 2019, 20:47:39) [MSC v.1916 64 bit (AMD64)]
c:\users\josepstr\appdata\local\programs\python\python38\python.exe
Windows 10

<Environment {
    "colors": 256,
    "config": {
        "__meta__": {
            "about": "HTTPie configuration file",
            "help": "https://httpie.org/doc#config",
            "httpie": "1.0.2"
        },
        "default_options": "['--ignore-stdin', '--print=hb']"
    },
    "config_dir": "C:\\Users\\josepstr\\AppData\\Roaming\\\\httpie",
    "is_windows": true,
    "stderr": "<colorama.ansitowin32.StreamWrapper object at 0x0000022778437820>",
    "stderr_isatty": false,
    "stdin": "<_io.TextIOWrapper name='<stdin>' mode='r' encoding='cp1252'>",
    "stdin_encoding": "cp1252",
    "stdin_isatty": false,
    "stdout": "<colorama.ansitowin32.StreamWrapper object at 0x00000227784379A0>",
    "stdout_encoding": "cp1252",
    "stdout_isatty": false
}>
HTTP/1.1 200 OK
Access-Control-Allow-Origin: *
Access-Control-Expose-Headers: ETag, Link, Location, Retry-After, X-GitHub-OTP, X-RateLimit-Limit, X-RateLimit-Remaining, X-RateLimit-Reset, X-OAuth-Scopes, X-Accepted-OAuth-Scopes, X-Poll-Interval, X-GitHub-Media-Type
Cache-Control: public, max-age=60, s-maxage=60
Content-Encoding: gzip
Content-Security-Policy: default-src 'none'
Content-Type: application/json; charset=utf-8
Date: Fri, 16 Aug 2019 14:02:10 GMT
ETag: W/"7dc470913f1fe9bb6c7355b50a0737bc"
Referrer-Policy: origin-when-cross-origin, strict-origin-when-cross-origin
Server: GitHub.com
Status: 200 OK
Strict-Transport-Security: max-age=31536000; includeSubdomains; preload
Transfer-Encoding: chunked
Vary: Accept
Vary: Accept-Encoding
X-Content-Type-Options: nosniff
X-Frame-Options: deny
X-GitHub-Media-Type: github.v3; format=json
X-GitHub-Request-Id: B6A5:47F7:1F73AB:2A67EC:5D56B762
X-RateLimit-Limit: 60
X-RateLimit-Remaining: 57
X-RateLimit-Reset: 1565967730
X-XSS-Protection: 1; mode=block

{
    "authorizations_url": "https://api.github.com/authorizations",
    "code_search_url": "https://api.github.com/search/code?q={query}{&page,per_page,sort,order}",
    "commit_search_url": "https://api.github.com/search/commits?q={query}{&page,per_page,sort,order}",
    "current_user_authorizations_html_url": "https://github.com/settings/connections/applications{/client_id}",
    "current_user_repositories_url": "https://api.github.com/user/repos{?type,page,per_page,sort}",
    "current_user_url": "https://api.github.com/user",
    "emails_url": "https://api.github.com/user/emails",
    "emojis_url": "https://api.github.com/emojis",
    "events_url": "https://api.github.com/events",
    "feeds_url": "https://api.github.com/feeds",
    "followers_url": "https://api.github.com/user/followers",
    "following_url": "https://api.github.com/user/following{/target}",
    "gists_url": "https://api.github.com/gists{/gist_id}",
    "hub_url": "https://api.github.com/hub",
    "issue_search_url": "https://api.github.com/search/issues?q={query}{&page,per_page,sort,order}",
    "issues_url": "https://api.github.com/issues",
    "keys_url": "https://api.github.com/user/keys",
    "notifications_url": "https://api.github.com/notifications",
    "organization_repositories_url": "https://api.github.com/orgs/{org}/repos{?type,page,per_page,sort}",
    "organization_url": "https://api.github.com/orgs/{org}",
    "public_gists_url": "https://api.github.com/gists/public",
    "rate_limit_url": "https://api.github.com/rate_limit",
    "repository_search_url": "https://api.github.com/search/repositories?q={query}{&page,per_page,sort,order}",
    "repository_url": "https://api.github.com/repos/{owner}/{repo}",
    "starred_gists_url": "https://api.github.com/gists/starred",
    "starred_url": "https://api.github.com/user/starred{/owner}{/repo}",
    "team_url": "https://api.github.com/teams",
    "user_organizations_url": "https://api.github.com/user/orgs",
    "user_repositories_url": "https://api.github.com/users/{user}/repos{?type,page,per_page,sort}",
    "user_search_url": "https://api.github.com/search/users?q={query}{&page,per_page,sort,order}",
    "user_url": "https://api.github.com/users/{user}"
}
>>> requests.request(**{
    "allow_redirects": false,
    "auth": "None",
    "cert": "None",
    "data": {},
    "files": {},
    "headers": {
        "User-Agent": "HTTPie/1.0.2"
    },
    "method": "get",
    "params": {},
    "proxies": {},
    "stream": true,
    "timeout": 30,
    "url": "https://api.github.com",
    "verify": true
})