В итоге я сделал данные и использовал ROW_NUMBER для определения последней покупки.
SELECT 1 AS CUST_ID
INTO #CUSTOMERS
UNION
SELECT 2
UNION
SELECT 3
UNION
SELECT 4
SELECT 1 AS CUST_ID, 'SLACKS' AS PANT_TYPE, CAST('1/1/2017' AS DATE) AS PANT_DATE
INTO #PANTS
UNION
SELECT 1, 'CARGO SHORTS', CAST('2/2/2018' AS DATE)
UNION
SELECT 1, 'SLACKS', CAST('3/3/2018' AS DATE)
UNION
SELECT 2, 'CARGO PANTS', CAST('2/2/2017' AS DATE)
UNION
SELECT 2, 'SLACKS', CAST('4/4/2018' AS DATE)
UNION
SELECT 3, 'CARGO PANTS', CAST('4/1/2018' AS DATE)
UNION
SELECT 3, 'SLACKS', CAST('5/8/2017' AS DATE)
UNION
SELECT 4, 'CARGO SHORTS', CAST('2/2/2018' AS DATE)
UNION
SELECT 4, 'SLACKS', CAST('3/3/2018' AS DATE)
UNION
SELECT 4, 'CARGO PANTS', CAST('2/2/2017' AS DATE)
UNION
SELECT 4, 'SLACKS', CAST('4/4/2018' AS DATE)
UNION
SELECT 4, 'CARGO PANTS', CAST('4/1/2018' AS DATE)
UNION
SELECT 4, 'SLACKS', CAST('5/8/2017' AS DATE)
SELECT 1 AS CUST_ID, 'POLO' AS SHIRT_TYPE, CAST('1/1/2017' AS DATE) AS SHIRT_DATE
INTO #SHIRTS
UNION
SELECT 1, 'POLO - LONG SLEEVE', CAST('2/2/2018' AS DATE)
UNION
SELECT 1, 'POLO - LONG SLEEVE', CAST('3/3/2018' AS DATE)
UNION
SELECT 2, 'POLO', CAST('2/2/2017' AS DATE)
UNION
SELECT 2, 'POLO - LONG SLEEVE', CAST('4/4/2018' AS DATE)
UNION
SELECT 3, 'T-SHIRT', CAST('4/1/2018' AS DATE)
UNION
SELECT 3, 'POLO', CAST('5/8/2017' AS DATE)
UNION
SELECT 4, 'T-SHIRT', CAST('2/2/2018' AS DATE)
UNION
SELECT 4, 'POLO', CAST('3/3/2018' AS DATE)
UNION
SELECT 4, 'T-SHIRT', CAST('2/2/2017' AS DATE)
UNION
SELECT 4, 'POLO - LONG SLEEVE', CAST('4/4/2018' AS DATE)
UNION
SELECT 4, 'T-SHIRT', CAST('4/1/2018' AS DATE)
UNION
SELECT 4, 'POLO', CAST('5/8/2017' AS DATE)
SELECT C.CUST_ID, P.PANT_TYPE, P.PANT_DATE,
S.SHIRT_TYPE, S.SHIRT_DATE
FROM #CUSTOMERS C
LEFT JOIN (SELECT CUST_ID, PANT_TYPE, PANT_DATE, ROW_NUMBER()OVER(PARTITION BY CUST_ID ORDER BY PANT_DATE DESC) AS ROW_NUM FROM #PANTS) P ON P.CUST_ID = C.CUST_ID AND P.ROW_NUM = 1
LEFT JOIN (SELECT CUST_ID, SHIRT_TYPE, SHIRT_DATE, ROW_NUMBER()OVER(PARTITION BY CUST_ID ORDER BY SHIRT_DATE DESC) AS ROW_NUM FROM #SHIRTS) S ON S.CUST_ID = C.CUST_ID AND S.ROW_NUM = 1