Progress initially awkward coming into trendy bars (7)
I believe the answer is:
inroads
'progress' is the definition.
(I've seen this before)
'initially awkward coming into trendy bars' is the wordplay.
'initially' says to take the initial letters.
'coming into' is an insertion indicator.
'trendy' becomes 'in'.
'bars' becomes 'rods' (I can't justify this - if you can you should give a lot more credence to this answer).
The first letter of 'awkward' is 'a'.
'in'+'rods'='inrods'
'a' inserted into 'inrods' is 'INROADS'.
Can you help me to learn more?
(Other definitions for inroads that I've seen before include "Ordains as offensives" , "advances" , "Encroachments" , "Hostile incursions" , "(Make) raids, intrusions (into)" .)