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The Winston Box Reviews
Updated June 24, 2025
The Winston Box
The Winston Box takes both its name and its inspiration from Sir Winston Churchill, former Prime Minister of the United Kingdom and one of the most stylish men to ever grace the planet.
$75
00 per month
Stay away from this company. Product is low quality and the price for the low quantity and quality is through the roof. At almost a $100 USD my last box i got a pair of thin nylon track pants and a 3 button polo. I picked the neutral color scheme and they kept sending pink/salmon and peach colored tops and only navy blue bottoms. the fit was some what acceptable but the overall value is not there for the price point. Save yourself the coin and dont subscribe
THE WINSTON BOX IS A TERRIBLE COMPANY. I ORDERED FROM CANADA AND MY ORDER TOOK 6-7 WEEKS TO ARRIVE EACH TIME… I BOOKED AND PAID FOR A MONTHLY SUBSCRIPTION. WHEN YOU EMAIL THEM, THEY DO NOT REPLY, APPOLOGIZE OR EVEN TRY TO SUPPORT YOU AS A CUSTOMER. READ THIS EVERYONE….
GO TO A STORE IN PERSON DO NOT ORDER FROM THIS COMPANY AND BE TREATED DISRESPECTFULLY-K. ERICKSON
BEWARE!!!THIS IS A VERY UNPROFESSIONAL COMPANY. I EMAILED THE ABOUT VERY LATE ORDERS AND THEY DO NOT REPLY. ALSO READ YOUR SIGN UP CAREFULLY. YOU PAY UPFRONT ON THE 5 OF THE MONTH AND IN OUT CASE IN THE SECOND MONTH OF SIGNING UP I AM STILL WAITING FOR LAST MONTHS ORDER NOW IT IS AUGUST 7, 24! GO TO A STORE WITH REAL PEOPLE
Had the subscription for nearly 2 years. Clothes fit great. Was happy with the value. My review is based on customer service. I had upgraded to their business box and received a couple of great boxes. On my final box I was charged however my box was never shipped. I contacted the company and was told fulfillment would look into it. Since that time I have had no contact from the company on any other platform. When I checked my site profile all my previous orders were deleted. No refund. No response.
I received boxes successfully for a year and a half. Last may I was charged nearly $300 for a box and now in September I still have not received it. All attempts to email…. call…. contact on social media go unanswered.
Not only is the customer service poor the quality of the clothing is even worse!!! I would expect better from a subscription service but Walmart has better quality than Winston Box at a lower price. Do yourself a favor don’t even try cause canceling is even worse. Still having issues and customer service is the worse I’ve ever had to deal with, VERY rude