diff --git a/base/docs/basedocs.jl b/base/docs/basedocs.jl
index fd8240cba9a32..3ab012ef97bc5 100644
--- a/base/docs/basedocs.jl
+++ b/base/docs/basedocs.jl
@@ -2320,7 +2320,7 @@ arguments accepted by varargs methods (see the section on [Varargs Functions](@r
 # Examples
 ```jldoctest
 julia> mytupletype = Tuple{AbstractString,Vararg{Int}}
-Tuple{AbstractString,Vararg{Int64,N} where N}
+Tuple{AbstractString,Vararg{Int64}}
 
 julia> isa(("1",), mytupletype)
 true
diff --git a/base/errorshow.jl b/base/errorshow.jl
index a4583bc819856..22deef06db09a 100644
--- a/base/errorshow.jl
+++ b/base/errorshow.jl
@@ -404,7 +404,7 @@ function show_method_candidates(io::IO, ex::MethodError, @nospecialize kwargs=()
             sig0 = method.sig
             while isa(sig0, UnionAll)
                 push!(tv, sig0.var)
-                iob = IOContext(iob, :unionall_env => sig0.var)
+                iob = IOContext(iob, :tv_standalone => sig0.var)
                 sig0 = sig0.body
             end
             s1 = sig0.parameters[1]
diff --git a/base/methodshow.jl b/base/methodshow.jl
index e878660a0305e..3bf54509dc962 100644
--- a/base/methodshow.jl
+++ b/base/methodshow.jl
@@ -61,7 +61,7 @@ function arg_decl_parts(m::Method, html=false)
     if length(argnames) >= m.nargs
         show_env = ImmutableDict{Symbol, Any}()
         for t in tv
-            show_env = ImmutableDict(show_env, :unionall_env => t)
+            show_env = ImmutableDict(show_env, :tv_standalone => t)
         end
         decls = Tuple{String,String}[argtype_decl(show_env, argnames[i], sig, i, m.nargs, m.isva)
                     for i = 1:m.nargs]
@@ -112,7 +112,7 @@ function show_method_params(io::IO, tv)
                 end
                 x = tv[i]
                 show(io, x)
-                io = IOContext(io, :unionall_env => x)
+                io = IOContext(io, :tv_standalone => x)
             end
             print(io, "}")
         end
diff --git a/base/show.jl b/base/show.jl
index 987a146d9ee5e..3e25e89bec81c 100644
--- a/base/show.jl
+++ b/base/show.jl
@@ -529,11 +529,81 @@ function show(io::IO, @nospecialize(x::Type))
         end
     end
 
+    # The `:unionall_tvs` io context records typevar naming data, i.e. whether
+    # the typevar needs a corresponding `where` being printed or not.
+    # It is being filled recursively here first before printing the typevar
+    # itself.
+    io = IOContext(io, :unionall_tvs => _unionall_tvs(io))
+    _unionall_name_tvs(io, x)
+
+    # The `:unionall_env => tv::TypeVar` io context is used to signify that
+    # io is happening within the unionall environment of `tv`.
     show(IOContext(io, :unionall_env => x.var), x.body)
-    print(io, " where ")
-    show(io, x.var)
+
+    if isnamed(io, x.var)
+        print(io, " where ")
+        show(io, x.var)
+    end
 end
 
+"""
+    isgensym(x::Symbol)
+
+Return whether `x` is an generated symbol, as generated by e.g.
+[`gensym`](@ref).
+"""
+isgensym(x::Symbol) = first(String(x)) == '#'
+
+_unionall_tvs(io::IO) = get(io, :unionall_tvs, IdDict{TypeVar,Int}())
+isnamed(io::IO, tv::TypeVar) = get(_unionall_tvs(io), tv, 0) > 1
+setnamed(io::IO, tv::TypeVar) = setindex!(_unionall_tvs(io), 2, tv)
+
+function _unionall_name_tvs(io::IO, @nospecialize x::UnionAll)
+    # collect typevar naming candidates
+    tvs = TypeVar[]
+    y = x
+    while y isa UnionAll
+        # if it is named then this method was called already on a parent
+        isnamed(io, y.var) && return io
+        push!(tvs, y.var)
+        y = y.body
+    end
+
+    if y isa DataType
+        # count typevar occurrences within the body recursively
+        isempty(_unionall_tvs(io)) && _count_tvs!(_unionall_tvs(io), y)
+
+        for tv in reverse(collect(y.parameters))
+            tv isa TypeVar || continue
+            # might have been named above or earlier in the printing hierarchy
+            isnamed(io, tv) && continue
+
+            if last(tvs) == tv && (tv.lb == Bottom || tv.ub == Any)
+                # safe for elision
+                pop!(tvs)
+                isempty(tvs) && return io
+            else
+                setnamed(io, tv)
+            end
+        end
+    end
+
+    # remaining ones need to be named, since anonymizing further nested
+    # occurences is disallowed, includes e.g. y::Union
+    foreach(tv -> isnamed(io, tv) || setnamed(io, tv), tvs)
+end
+
+@nospecialize
+_count_tvs!(counts) = counts
+_count_tvs!(counts, x) = counts
+_count_tvs!(counts, x::TypeVar) =
+    (setindex!(counts, get(counts, x, 0) + 1, x); _count_tvs!(counts, x.lb, x.ub))
+_count_tvs!(counts, x::UnionAll) = _count_tvs!(counts, x.var.lb, x.var.ub, x.body)
+_count_tvs!(counts, x::Union) = _count_tvs!(counts, x.a, x.b)
+_count_tvs!(counts, x::DataType) = _count_tvs!(counts, x.parameters...)
+_count_tvs!(counts, x1, x2, x...) = (_count_tvs!(counts, x1); _count_tvs!(counts, x2, x...))
+@specialize
+
 # Check whether 'sym' (defined in module 'parent') is visible from module 'from'
 # If an object with this name exists in 'from', we need to check that it's the same binding
 # and that it's not deprecated.
@@ -596,12 +666,29 @@ function show_datatype(io::IO, x::DataType)
             print(io, "NTuple{", n, ',', x.parameters[1], "}")
         else
             show_type_name(io, x.name)
-            # Do not print the type parameters for the primary type if we are
-            # printing a method signature or type parameter.
-            # Always print the type parameter if we are printing the type directly
-            # since this information is still useful.
+
+            if !istuple
+                # find out up until which parameter we need to print typevars
+                y = x.name.wrapper
+                n, j = 0, 0
+                while y isa UnionAll
+                    j += 1
+                    tv = x.parameters[j]
+                    if !isa(tv, TypeVar) || isnamed(io, tv) ||
+                            in(:tv_standalone => tv, io) || !in(:unionall_env => tv, io) ||
+                            # can only elide when typevar constraints are
+                            # the same as defined in the parametric type itself
+                            isa(tv.lb, TypeVar) || isa(tv.ub, TypeVar) ||
+                            !(tv.lb == y.var.lb) || !(tv.ub == y.var.ub)
+                        n = j
+                    end
+                    y = y.body
+                end
+                n == 0 && return
+            end
+
             print(io, '{')
-            for (i, p) in enumerate(x.parameters)
+            for (i, p) in enumerate(x.parameters[1:n])
                 show(io, p)
                 i < n && print(io, ',')
             end
@@ -1780,7 +1867,7 @@ function show_tuple_as_call(io::IO, name::Symbol, sig::Type, demangle=false, kwa
     env_io = io
     while isa(sig, UnionAll)
         push!(tv, sig.var)
-        env_io = IOContext(env_io, :unionall_env => sig.var)
+        env_io = IOContext(env_io, :tv_standalone => sig.var)
         sig = sig.body
     end
     sig = sig.parameters
@@ -1837,12 +1924,6 @@ function ismodulecall(ex::Expr)
 end
 
 function show(io::IO, tv::TypeVar)
-    # If we are in the `unionall_env`, the type-variable is bound
-    # and the type constraints are already printed.
-    # We don't need to print it again.
-    # Otherwise, the lower bound should be printed if it is not `Bottom`
-    # and the upper bound should be printed if it is not `Any`.
-    in_env = (:unionall_env => tv) in io
     function show_bound(io::IO, @nospecialize(b))
         parens = isa(b,UnionAll) && !print_without_params(b)
         parens && print(io, "(")
@@ -1850,24 +1931,41 @@ function show(io::IO, tv::TypeVar)
         parens && print(io, ")")
     end
     lb, ub = tv.lb, tv.ub
-    if !in_env && lb !== Bottom
-        if ub === Any
-            show_unquoted(io, tv.name)
-            print(io, ">:")
-            show_bound(io, lb)
-        else
+
+    # the `:tv_standalone => tv::TypeVar` io context tells to print the typevar
+    # `tv` without any typebounds, this is not necessarily related to being
+    # within a unionall environment
+    (:tv_standalone => tv) in io && return show_unquoted(io, tv.name)
+
+    if (:unionall_env => tv) in io
+        # within unionall type argument for `tv`
+        if isnamed(io, tv)
+            # named typevars get their constraints printed after `where`
+            return show_unquoted(io, tv.name)
+        elseif lb == Bottom
+            # anonymous upper bound, need to show `<:Any` even if trivial
+            return print(io, "<:", ub)
+        elseif ub == Any
+            # anonymous non-trivial lower bound
+            return print(io, ">:", lb)
+        end
+        @assert false
+    elseif lb != Bottom && ub == Any
+        show_unquoted(io, tv.name)
+        print(io, ">:")
+        return show_bound(io, lb)
+    else
+        if lb != Bottom
             show_bound(io, lb)
             print(io, "<:")
-            show_unquoted(io, tv.name)
         end
-    else
         show_unquoted(io, tv.name)
+        if ub != Any
+            print(io, "<:")
+            show_bound(io, ub)
+        end
     end
-    if !in_env && ub !== Any
-        print(io, "<:")
-        show_bound(io, ub)
-    end
-    nothing
+    return nothing
 end
 
 module IRShow
@@ -2027,19 +2125,19 @@ end
 
 # Types
 function dump(io::IOContext, x::DataType, n::Int, indent)
-    print(io, x)
+    tvar_io = io
+    for tparam in x.parameters
+        # approximately recapture the list of tvar parameterization
+        # that may be used by the internal fields
+        if isa(tparam, TypeVar)
+            tvar_io = IOContext(tvar_io, :tv_standalone => tparam)
+        end
+    end
+    print(tvar_io, x)
     if x !== Any
-        print(io, " <: ", supertype(x))
+        print(tvar_io, " <: ", supertype(x))
     end
     if n > 0 && !(x <: Tuple) && !x.abstract
-        tvar_io::IOContext = io
-        for tparam in x.parameters
-            # approximately recapture the list of tvar parameterization
-            # that may be used by the internal fields
-            if isa(tparam, TypeVar)
-                tvar_io = IOContext(tvar_io, :unionall_env => tparam)
-            end
-        end
         if x.name === NamedTuple_typename && !(x.parameters[1] isa Tuple)
             # named tuple type with unknown field names
             return
diff --git a/doc/src/devdocs/types.md b/doc/src/devdocs/types.md
index d8401258430f2..1ca4e0fdaf6d3 100644
--- a/doc/src/devdocs/types.md
+++ b/doc/src/devdocs/types.md
@@ -252,7 +252,7 @@ julia> Tuple
 Tuple
 
 julia> Tuple.parameters
-svec(Vararg{Any,N} where N)
+svec(Vararg{Any})
 ```
 
 Unlike other types, tuple types are covariant in their parameters, so this definition permits
diff --git a/doc/src/manual/types.md b/doc/src/manual/types.md
index c29c85500e130..38964b29c7306 100644
--- a/doc/src/manual/types.md
+++ b/doc/src/manual/types.md
@@ -901,7 +901,7 @@ of trailing elements:
 
 ```jldoctest
 julia> mytupletype = Tuple{AbstractString,Vararg{Int}}
-Tuple{AbstractString,Vararg{Int64,N} where N}
+Tuple{AbstractString,Vararg{Int64}}
 
 julia> isa(("1",), mytupletype)
 true
@@ -1089,7 +1089,7 @@ consider the two types created by the following declarations:
 
 ```jldoctest
 julia> const T1 = Array{Array{T,1} where T, 1}
-Array{Array{T,1} where T,1}
+Array{Array{<:Any,1},1}
 
 julia> const T2 = Array{Array{T,1}, 1} where T
 Array{Array{T,1},1} where T
diff --git a/stdlib/InteractiveUtils/src/InteractiveUtils.jl b/stdlib/InteractiveUtils/src/InteractiveUtils.jl
index a2abf8730cd84..0b6bb46718cb1 100644
--- a/stdlib/InteractiveUtils/src/InteractiveUtils.jl
+++ b/stdlib/InteractiveUtils/src/InteractiveUtils.jl
@@ -298,7 +298,7 @@ function dumpsubtypes(io::IO, x::DataType, m::Module, n::Int, indent)
                     tp = t
                     while true
                         show(tvar_io, tp.var)
-                        tvar_io = IOContext(tvar_io, :unionall_env => tp.var)
+                        tvar_io = IOContext(tvar_io, :tv_standalone => tp.var)
                         tp = tp.body
                         if isa(tp, UnionAll)
                             print(io, ", ")
diff --git a/stdlib/InteractiveUtils/test/runtests.jl b/stdlib/InteractiveUtils/test/runtests.jl
index 7bbc2b321a440..691e52d5d2fc8 100644
--- a/stdlib/InteractiveUtils/test/runtests.jl
+++ b/stdlib/InteractiveUtils/test/runtests.jl
@@ -56,7 +56,7 @@ end
 Base.getindex(A::Stable, i) = A.A[i]
 Base.getindex(A::Unstable, i) = A.A[i]
 
-tag = "ARRAY{FLOAT64,N}"
+tag = "ARRAY{FLOAT64}"
 @test warntype_hastag(getindex, Tuple{Unstable{Float64},Int}, tag)
 @test !warntype_hastag(getindex, Tuple{Stable{Float64,2},Int}, tag)
 @test warntype_hastag(getindex, Tuple{Stable{Float64},Int}, tag)
diff --git a/test/errorshow.jl b/test/errorshow.jl
index 04a1176c45ea9..c104c10786bec 100644
--- a/test/errorshow.jl
+++ b/test/errorshow.jl
@@ -430,7 +430,7 @@ let err_str,
     @test startswith(sprint(show, which(FunctionLike(), Tuple{})),
                      "(::$(curmod_prefix)FunctionLike)() in $curmod_str at $sp:$(method_defs_lineno + 7)")
     @test startswith(sprint(show, which(StructWithUnionAllMethodDefs{<:Integer}, (Any,))),
-                     "($(curmod_prefix)StructWithUnionAllMethodDefs{T} where T<:Integer)(x)")
+                     "($(curmod_prefix)StructWithUnionAllMethodDefs{<:Integer})(x)")
     @test repr("text/plain", FunctionLike()) == "(::$(curmod_prefix)FunctionLike) (generic function with 1 method)"
     @test repr("text/plain", Core.arraysize) == "arraysize (built-in function)"
 
diff --git a/test/reflection.jl b/test/reflection.jl
index 4b77f2e2ac058..54f126338e111 100644
--- a/test/reflection.jl
+++ b/test/reflection.jl
@@ -214,7 +214,7 @@ let ex = :(a + b)
 end
 foo13825(::Array{T, N}, ::Array, ::Vector) where {T, N} = nothing
 @test startswith(string(first(methods(foo13825))),
-                 "foo13825(::Array{T,N}, ::Array, ::Array{T,1} where T)")
+                 "foo13825(::Array{T,N}, ::Array, ::Array{<:Any,1})")
 
 mutable struct TLayout
     x::Int8
diff --git a/test/show.jl b/test/show.jl
index ade7cb361f8d6..fa67b1787684f 100644
--- a/test/show.jl
+++ b/test/show.jl
@@ -1472,6 +1472,8 @@ function + end
 function == end
 end
 
+is_juliarepr(x) = eval(Meta.parse(repr(x))) == x
+
 @testset "Parseable printing of types" begin
     @test repr(typeof(print)) == "typeof(print)"
     @test repr(typeof(Base.show_default)) == "typeof(Base.show_default)"
@@ -1490,12 +1492,60 @@ end
 end
 
 let x = TypeVar(:_), y = TypeVar(:_)
-    @test repr(UnionAll(x, UnionAll(y, Pair{x,y}))) == "Pair{_1,_2} where _2 where _1"
-    @test repr(UnionAll(x, UnionAll(y, Pair{UnionAll(x,Ref{x}),y}))) == "Pair{Ref{_1} where _1,_1} where _1"
+    @test repr(UnionAll(x, UnionAll(y, Pair{x,y}))) == "Pair"
+    @test repr(UnionAll(x, UnionAll(y, Pair{UnionAll(x,Ref{x}),y}))) == "Pair{Ref}"
     x = TypeVar(:a)
     y = TypeVar(:a)
     z = TypeVar(:a)
-    @test repr(UnionAll(z, UnionAll(x, UnionAll(y, Tuple{x,y,z})))) == "Tuple{a1,a2,a} where a2 where a1 where a"
+    @test repr(UnionAll(z, UnionAll(x, UnionAll(y, Tuple{x,y,z})))) == "Tuple{<:Any,<:Any,a} where a"
+end
+
+@testset "unionall types" begin
+    X = TypeVar(gensym())
+    Y = TypeVar(gensym(), Ref, Ref)
+    x, y, z = TypeVar(:a), TypeVar(:a), TypeVar(:a)
+    struct TestTVUpper{A<:Integer} end
+
+    # named typevars
+    @test is_juliarepr(Ref{A} where A)
+    @test is_juliarepr(Ref{A} where A>:Ref)
+    @test is_juliarepr(Ref{A} where A<:Ref)
+    @test is_juliarepr(Ref{A} where Ref<:A<:Ref)
+    @test is_juliarepr(TestTVUpper{<:Real})
+    @test is_juliarepr(TestTVUpper{<:Integer})
+    @test is_juliarepr(TestTVUpper{<:Signed})
+
+    # typearg order
+    @test is_juliarepr(UnionAll(X, Pair{X,<:Any}))
+    @test is_juliarepr(UnionAll(X, Pair{<:Any,X}))
+
+    # duplicates
+    @test is_juliarepr(UnionAll(X, Pair{X,X}))
+
+    # nesting
+    @test is_juliarepr(UnionAll(X, Ref{Ref{X}}))
+    @test is_juliarepr(Union{T, Int} where T)
+    @test is_juliarepr(Pair{A,<:A} where A)
+
+    # renumbered typevars with same names
+    @test is_juliarepr(UnionAll(z, UnionAll(x, UnionAll(y, Tuple{x,y,z}))))
+
+    # shortened typevar printing
+    @test repr(Ref{<:Any}) == "Ref"
+    @test repr(Pair{1,<:Any}) == "Pair{1}"
+    @test repr(Ref{<:Ref}) == "Ref{<:Ref}"
+    @test repr(Ref{>:Ref}) == "Ref{>:Ref}"
+    @test repr(Pair{<:Any,1}) == "Pair{<:Any,1}"
+    yname = sprint(Base.show_unquoted, Y.name)
+    @test repr(UnionAll(Y, Ref{Y})) == "Ref{$yname} where Ref<:$yname<:Ref"
+    @test endswith(repr(TestTVUpper{<:Real}), "TestTVUpper{<:Real}")
+    @test endswith(repr(TestTVUpper{<:Integer}), "TestTVUpper")
+    @test endswith(repr(TestTVUpper{<:Signed}), "TestTVUpper{<:Signed}")
+
+    # exception for tuples
+    @test is_juliarepr(Tuple)
+    @test is_juliarepr(Tuple{})
+    @test is_juliarepr(Tuple{<:Any})
 end
 
 @testset "showarg" begin
@@ -1564,7 +1614,7 @@ end
     @test showstr([Float16(1)]) == "Float16[1.0]"
     @test showstr([[Float16(1)]]) == "Array{Float16,1}[[1.0]]"
     @test replstr(Real[Float16(1)]) == "1-element Array{Real,1}:\n Float16(1.0)"
-    @test replstr(Array{Real}[Real[1]]) == "1-element Array{Array{Real,N} where N,1}:\n [1]"
+    @test replstr(Array{Real}[Real[1]]) == "1-element Array{Array{Real},1}:\n [1]"
     # printing tuples (Issue #25042)
     @test replstr(fill((Int64(1), zeros(Float16, 3)), 1)) ==
                  "1-element Array{Tuple{Int64,Array{Float16,1}},1}:\n (1, [0.0, 0.0, 0.0])"
@@ -1591,7 +1641,7 @@ end
     end
 
     # issue #25857
-    @test repr([(1,),(1,2),(1,2,3)]) == "Tuple{$Int,Vararg{$Int,N} where N}[(1,), (1, 2), (1, 2, 3)]"
+    @test repr([(1,),(1,2),(1,2,3)]) == "Tuple{$Int,Vararg{$Int}}[(1,), (1, 2), (1, 2, 3)]"
 
     # issues #25466 & #26256
     @test replstr([:A => [1]]) == "1-element Array{Pair{Symbol,Array{$Int,1}},1}:\n :A => [1]"
@@ -1611,9 +1661,9 @@ end
     @test replstr([[1.0]=>1.0]) == "1-element Array{Pair{Array{Float64,1},Float64},1}:\n [1.0] => 1.0"
 
     # issue #28159
-    @test replstr([(a=1, b=2), (a=3,c=4)]) == "2-element Array{NamedTuple{names,Tuple{$Int,$Int}} where names,1}:\n (a = 1, b = 2)\n (a = 3, c = 4)"
+    @test replstr([(a=1, b=2), (a=3,c=4)]) == "2-element Array{NamedTuple{<:Any,Tuple{$Int,$Int}},1}:\n (a = 1, b = 2)\n (a = 3, c = 4)"
 
-    @test replstr(Vector[Any[1]]) == "1-element Array{Array{T,1} where T,1}:\n Any[1]"
+    @test replstr(Vector[Any[1]]) == "1-element Array{Array{<:Any,1},1}:\n Any[1]"
     @test replstr(AbstractDict{Integer,Integer}[Dict{Integer,Integer}(1=>2)]) ==
         "1-element Array{AbstractDict{Integer,Integer},1}:\n Dict(1 => 2)"
 
@@ -1834,7 +1884,7 @@ end
 
 @testset """printing "Any" is not skipped with nested arrays""" begin
     @test replstr(Union{X28004,Vector}[X28004(Any[X28004(1)])], :compact => true) ==
-        "1-element Array{Union{X28004, Array{T,1} where T},1}:\n X(Any[X(1)])"
+        "1-element Array{Union{X28004, Array{<:Any,1}},1}:\n X(Any[X(1)])"
 end
 
 # Issue 25589 - Underlines in cmd printing