I've been a regular customer at this Winners location for years, but my most recent visit has left me so uncomfortable that I won't be returning to this location Ever! Today, I needed to return one item and exchange another for a smaller size. Everything went smoothly until checkout. The cashier, a woman about 5'3" tall, with dark brown skin, black boy cut hair, and appearing to be in her late 50s (maybe) was for some reason angry from the start. I greeted her politely with, "Hi, how's it going?" She ignored me completely. When I explained I wanted to return an item and pulled it out, she processed it with an angry look. As I started to mention the second item ("And this one as well..."), she cut me off mid-sentence and yelled, "WAIT! LET ME DO THIS FIRST!" I was shocked and caught off guard. She then said in an angry tone and look, "We're only giving store credit." I replied calmly, "Okay, that's fine." But the issues continued: She tried swiping the gift card to load the funds, but it wouldn't work. She got angry and said, "Why isn't this working?!" and smacked the card against the reader repeatedly before continuing. To top it off, she made me stand there for a full 10 minutes while she slowly attached pins, magnets, and hangers to the returned items while I was staring at her irritated expression the whole time before finally processing my exchange. As someone with 3 years of retail experience, I know good customer service, and this was the opposite. I don't know what their training is like, but it's clearly not preparing staff to handle basic transactions with respect. This rude, inefficient experience has ended my loyalty to this store I'll shop elsewhere from now on. read more

I have been a long-time customer at this Winners and have always found the staff polite and welcoming. I have shopped here throughout my undergraduate years and many staff even know me by name. However, today, September 10, 2025, after purchasing an item, a fellow customer confronted me outside the store and accused me of not paying even though I had my receipt and had done nothing wrong. Because Ontario retailers charge for reusable bags, I always bring my own. At this location the large bag is about $1.49. I was using my own school tote bag because it had plenty of extra space and I did not need to purchase a bag from the store. After paying for my jeans and receiving my receipt I placed them in my tote. While on the phone with a friend I briefly took the jeans out to admire my purchase for my lovely mother. Winners' motto is "Find Fabulous for Less," and I truly appreciated finding such a good deal for her. Perhaps the woman mistook me for talking to myself, but I would never steal. It is wrong to make assumptions like that about anyone without proof. A middle-aged white woman with blonde hair tied in a bun, wearing a black and white striped sweater, large gold earrings, blue jeans, Gucci GG motif flat shoes and a brown crossbody bag, and carrying a small black and white bulldog or terrier-type dog apparently assumed I had not paid. She picked up her dog, followed me onto the escalator and I went down ahead of her. At the bottom she began questioning me loudly. She asked, "Did you pay for those jeans?" and then said words to the effect of, "Oh, because that looked very suspicious/sketchy" in a sarcastic tone. From what I could tell she had not purchased anything herself. Her manner came across as arrogant and unnecessarily rude. It felt like I was being policed by someone with no authority, and it was upsetting and embarrassing. People should think before they speak and should not make false assumptions about others because it is not right or kind. My mom later tried the jeans on and they fit her perfectly with plenty of room to spare, and she thanked me for finding such a great deal. I told my parents and those around me and everyone was upset on my behalf. I have reported this incident to the appropriate channels and multiple sources. This was the first time anyone has ever treated me this way at Winners. Until now everyone at this location has always been friendly and welcoming, so this incident was very upsetting and left me shaken. I know there are other, better locations I have been to, and although I will miss the staff here and the memories I have had over the past couple of years, this experience has left a sour taste in my mouth. Canada is a multicultural and diverse country and everyone deserves to be treated with respect regardless of their wealth, ethnicity or religion. I do not use Yelp often but felt compelled to share my experience so that no one else is treated this way. read more

Winners - Men's Clothing Near Me - Toronto, Ontario

Good Winners location on the 2nd floor of a building. Somewhat limited in selection but they have some nice high end options. Noticed on my last visit that they have expanded and added a Homesense further east on the floor. Lots of great decorating options. Nice to have a Winners that is easy to get to. It is around the corner from the Bay subway. Right now they have lots of gift items for Christmas! ..and some great ugly Christmas sweaters. Gets pretty busy during peak hours and you might have to wait to check out. read more

This is my favourite Winners in the city (I haven't visited them all, but most). Since it's located in Yorkville, they carry a lot of higher-end fashion brands. The second floor has accessories (shoes, handbags, belts, hair accessories, soaps & shampoos, etc). Plus a really nice jewelry section (not all Winners have $$ bling bling $$ jewelry) The 3rd floor has all the clothes (mens & womens), swimwear, lingerie plus kitchen & bath products and the change rooms at the far end. It's mostly clothes, really. Like most Winners locations, the change room facilities kind of suck, I always get a slow-moving attendant coping attitude and treating me like a criminal even though I just want to try on clothes. Check-out is also somewhat sucky, usually meriting a 5-10 minute wait to pay, but nothing extreme. The awesome clothes/deals make up for the customer service faux-pas'. read more

Truth be told, Winners makes me long for a bygone age of retail when the customer was king (or queen). I remember walking into Winners as a kid, only when I had to. Rows upon rows of scratchy pants and factory seconds. My mom sorting through poorly-sized racks, vainly calling for help from disinterested sales associates, only to give up in frustration and haul us down to Eatons, where the prices were higher but we were guaranteed to find good quality, well tailored merch sold by people who knew our sizes just by looking at us. Sadly, Eatons is long gone (along with Simpsons and a host of other mid-upper market retailers) while Winners remains. To be fair, it's gotten better. You're still on your own when it comes to finding stuff (unless you wanna buy a watch. The glass case is usually well-staffed with people who know their stuff), but the brands are mid-to-high end and if you go in with an open mind chances are you'll leave with something that suits you. I love a good bargain hunt, but Winners is still not how I prefer to shop. It's great for one-off purchases or gifts, but if I'm putting a wardrobe together I often follow the advice of David Suzuki (not a natty dresser, but he makes a good point). If I find something that fits and looks good on me, I try to purchase a few items across a range of colors. Easier, more uniform, less time hunting through racks. If only Winners left me feeling better than a draw. read more

Having not visited this location for a year or two, the first thing that caught my eye was that they've went through some serious renovation since. There's a lot more black decor which gives it a more luxurious feel, especially when you're at check out. I came here after work to kill time and I stayed way longer than I expected. The HomeSense section drew me in big time! It is small but it had a lot to offer for what I needed. What I appreciated the most was that only some items are picked through so you still had options. Their decor and organizational products are so super chic which matches my style perfectly​. I was also tempted by some of their furniture offerings! I ended up walking away with a couple of small clearance items but I'll keep checking back as I want to redecorate my space. On the winners side, I feel like their clothing and footwear are lackluster. It could be that I've grown out of shopping in an atmosphere like winners. However, I will still visit a winners every now and then in case of some good fashion finds! read more

I love Winners, but I'm continually disappointed in this Winners. Being on Bloor and Avenue there is a much higher percentage of high end designer goods. There's actually a separate section for them. I love to stare and touch all these gorgeous items. Some are decently priced (still expensive but at least somewhat in reach as a one time treat). But the rest of the Winners is cramped (women's clothing section) and has dim lighting and surprisingly not a lot of good selection. It's like yawn. I do like the shoe section and the jewellery section and he home section, but the clothing section is seriously lacking. They draw you in with the beautiful high end designer section and then a huge letdown with the clothing for the regular people like me. I'll always stop in when I'm in the area just to see what bargains I might find (oh the lure of a bargain can make me go anywhere..lol) but I don't think I've ever bought anything at this location, read more

I agree with Angel L's review. There is nothing that blew me away there either. Things also looked as thought they'd been picked over 100 times. The racks are way too overstocked which means (a) you can't see things perfectly (b) things keep falling off the rack(s). Even the spice/marinade section in the Home Sense area was a bit lacklustre. I bought a box of Scottish shortbread which seemed like a good idea/deal at the time - except there was no discerneable taste of butter, i.e. lower end brand. read more

Far better than the disaster that is at college and Yonge. The addition of home sense adds a lot. Lines can get long, overall a better than average location. read more

The way I feel about Winners is the way I feel about cupcakes. It makes total sense that I should love it and eat it more often than the average person, but I can't seem to ever walk away with anything. Sure, I'll go in and gawk for hours on end, try on their boots, feel the bathrobes and imagine myself in them, but for some reason, there's never anything that blows me away. Then they added HomeSense, and I thought, YES, now that I have a place to furnish, this will DEFINITELY be the place to go! Lovely new renovations, always new things to pick up and ponder about. But nope...never a purchase again! Despite all this, I still have deep Winners love. I love it in the way that I feel like, one day, it's all going to click and I'll be buying things nonstop! Until then, they are my source of endless strolling and "maybe today!" checking in. read more

Winners feels like an Outlet store's Outlet store. The 'good deals' and 'fashion finds' are practically nonexistent; all the supposed good finds have been picked. Maybe woman find the good deals but from a Male's perspective, it's just a waste of time. Unless you're a size XXXL, you're not going to find anything worth buying. And good luck finding the entrance if you come from Cumberland and not Bloor Street. I was fed up before I even entered the place. The whole Winners "experience" just feels depressing. The fluorescent lighting, the rusted metal racks, clothing fallen to the floor from misshapen wire hangers, the sad looking staff. I think as a brand they need to put as much effort into the store as they do in the advertising. read more

This place is dangerous. Though the truly fantastic finds are far and few in between, it's a struggle for me to walk out of Winners without something in hand. On the things I look out for... on the first floor, the woman shoe selection is ever changing and excellent eye candy. The skin/perfume section is eclectic, though with some interesting brands and things with beautiful packaging, if you spent a bit of time searching the shelves. The women's clothing selection on the second floor is so-so despite the breadth of merchandise. The men stuff is really dismal though. Again, there's a wide selection, but I really haven't been able to find anything good in there. The stand out for me at this Winners is the home productions section! There's always so many pretty things in there that I just want - lovely notebooks, interesting pillows, random things like SIGG water bottles on the cheap. Winners always kind of feel like a large garage sale to me, but if you're willing to hunt and have a bit of time, there is treasure to be found. read more

I like this Winners. Not only is it a refreshing change from the many overpriced clothing retailers in the Yorkville area, but the mens section actually has a good amount of variety. I've managed to find everything from nice casual denim and collared shirts up to more formal work slacks, dress shirts and even a couple of ties. I'd say its a toss up between this one and the College Park for what I would consider to be the best Winners in Toronto, so it's definitely worth a stop in if you're up for some rack digging as per the usual Winners shopping style requirements. read more

I frequent this Winners since it's on my walk home from work (I usually dream up something I "need" about two seconds into my walk). I actually prefer the selection at the Yonge and College location, but that place is a zoo and out of my way. The line ups here are much shorter (tip - they have checkouts on the 1st and 2nd level) and don't make you want to rage out. I had a return to make here yesterday and I was super impressed by how painless it was! I had accidentally bought the wrong strength of mousse ("Strong" instead of "Lighweight"...makes a helluva difference - it was like putting concrete in my hair) and was really worried that they'd make a fuss since it had been opened. I nervously approached the returns desk and started to bust into my long drawn out concrete-hair-tale-of-woe and the cashier just stopped me and said it wasn't a problem. Anyone who has ever tried to make a return before will appreciate how easy it is here! read more

The bonus of working the night shift is that I had the whole day free to peruse Winners, something that takes quite a bit of time. Or frequent visits. Winners works in weird ways. It's hit or miss if you want to find something good. I found as I was looking through racks and racks, that with all the ugly clothes you wouldn't wear, you find something that is remotely okay, and you send up putting it in your pile to the dressing room. If you saw the item on it's own, you would never grab it. I really had to evaluate the choice before I bought them. If you go in without a plan, I think you'll come out with something you didn't need, or get frustrated or come out with a hidden gem. If you want something specific, it's like you need to visit the store after every shipment to see if they have that thing you want, and you have to be close by. No matter what, either you find it or you don't. Don't go in expecting to walkout with an item. Or be really really patient. I like how the sizes are marked on the hangers for easy elimination. Not much choice in this store for the Smalls, more Mediums. It's also a great choice to find basic purses, belts and fancy housewares. read more

My best experience here was when I needed some athletic gear for baseball. Just had to get a handful of inexpensive t-shirts that I could roll around in and not get mad if it ripped or got dirty. I thought for sure Winners selection would be mad corny -- which it was -- but they also had some really quality Puma and Adidas gear for dirt cheap. I wound up getting about 4-5 simple t-shirts for about 7-10 bucks each. Even grabbed a really nice Puma zip-up for less than 20 bucks! I try to swing by this location once and awhile to see if I can dig up some quality clothing, but the odds of finding something I find decent are usually pretty slim. Once came here hoping to find some new jeans and was greeted by some of the ugliest Jersey Shore-esque designs I've ever seen. It's like the Toronto club district exploded in front of my face. Same usually goes for a lot of their shirts, but it's always worth checking out. 9 times out of 10 though I tend to find some great Ben Sherman or Penguin article that's way too small for me. Sometimes the line-ups at the checkout are ridiculous and unbearable. There's actually been a couple of times I've had a purchase in my hand that I was already on the fence about that I wind up discarding because the line is a mile long. Women seem to love this store and they can easily roll up to the cashiers with a whole new wardrobe. read more

I used to be a huge Winners fan, but lately they've been getting on my nerves. But even before I stopped being a fan, I was never into this location. It's TOO BIG. Holy crap. Winners is hard enough to digest sometimes -- but this one is just floors upon floors of stuff that you have to rummage through to find something decent. It's exhausting! I really can't be bothered to go through every single shirt in the hopes that one of them won't be a sequined tie-dyed strappy concoction and it might fit well enough to be purchased. That said, if you are a Winners fan, you will like this location for two reasons: #1) They have more high-end stuff. It is on Bloor, after all. They carry last season's Prada, Gucci, Miu Miu and more. They have expensive shoes and expensive bags at discount prices. Just make sure you snatch them up before anyone else. #2) Huge selection. A floor of accessories and racks upon racks of jeans? Can't go wrong. If you don't want to spend a long time in here, then don't go in. The place is too big to zip around, and it's usually pretty crowded too. But if you're there in the right place at the right time, you might just get a good deal. read more

I find certain Winners much easier to find things in than others. This is one of the 'others' I really like it and all, and I guess based on its location I have noticed it had more 'higher end' names than some of the other locations around the city (or is that my imagination?) but when I'm in a cheap-o mood, that often results in leaving the store empty handed. And finding your way up and downstairs always confuses me even though I've been there a gazillion times. It's quite pretty, though. read more

We went to visit this Winners to pick up some luggage (And an Iron Man Mr. Potato Head. Tony Starch! hah) We had a question, and asked a girl named Rosa. It was a seemingly simple question, but took a little more work than we thought. Rosa stuck with us the whole way, finding out who we had to speak to, and getting everything done for us. Simply great customer service. Also, I like how the selection tries to be Yorkville, but the prices are still very Winners. read more

I really struggled with how to rate this Winners... First of all I don't like the store layout. If you are trying to access it from the Bloor street doors you are fine, but any other entrances require a map, a compass and some patience! All bitching aside, once you enter this location it's actually pretty descent selection of shoes and handbags. I never venture upstairs to their clothing and house wares department. I find their clothing selection mediocre especially their dresses rack. They due however carry a few designer lines as part of their Runway collection. Checkout at this place is sort of a nightmare. There is one checkout on the first floor and half the time no one is there. There is a jewellery counter checkout but since everything is under glass they are usually busy with helping customers with jewellery. There is a bigger checkout area upstairs but again there is usually no one there and the lines can get pretty long. Even though this store is kind of disappointing for a Yorkville location, I am going to give this Winners a 3 star; they do manage to carry some nice merchandise. They are by far not the worse or the best Winners I've been to and I would only recommend it if you are in the area. read more

This Winners location at Bloor and Avenue probably carries a lot higher end brands than the other locations because of the proximity to Yorkville. Also, the women's clothing, shoes and handbags departments takes the most space of the two floors. Since the renovations, the layout has significantly improved making the shopping experience a more enjoyable one. The store still gets a lot of customers, but it's definitely not as chaotic as the Winners at College Park. This Winners is also attached to a HomeSense store on the second floor through the men's department, so definitely a convenience if you're looking for houseware items and miscellaneous seasonal items as they always have plenty of selections. The staff are usually friendly, fast and efficient like most Winners as they manage the lines pretty effectively. So checkout is often a breeze and you never wait longer than 5-10 minutes. read more

This location has slowly been going downhill for the last two years. I usually stop in every few months to see what is there but I rarely find anything I like. The appearance of the store has also been in decline, I find more and more that it is frequently disheveled looking with clothing strewn about on top of the racks and on the floor. Despite this, the last time I was in there the line ups to pay were wrapped around the store so some people must be finding things that they like. read more

I went here this afternoon during my lunch break to shop for some random accents at Home Sense for our apartment. When I looked up this location online beforehand, I didn't realize that it was a 2-in-1 shop with Winners that shared the exact same space. I didn't realize it until I arrived there since the other Home Sense locations I have been to actually have a whole store to themselves. My overall description of this Bloor location in a few words would be like 85 percent Winners and 15 percent Home Sense. The Home Sense was literally one small room hidden away on the second floor, which took me a few minutes to find, while Winners has several floors of its products. Of course, that one little Home Sense room had a very limited selection of stuff. However, on the plus side, I found two high quality items that were on sale for quite a bargain. Luckily, the letter holder that I've been looking for was on sale for $4.99 and was still in decent condition but it was the last one at this location so I quickly claimed it, leaving that aisle with only those cheap unatractive looking metal ones remaining. I also found a pack of high quality bottle stoppers for only $6.99. Customer service was satisfactory but nothing exceptional. The guy who helped me out seemed a bit flustered. He was like "Oh no, the previous customer forgot her container. I'll be with you in a minute" and he rushed after her. When he finally came back and completed my sale, he still looked absent-minded and probably didn't hear me saying "Have a nice afternoon " because he didn't respond back. In conclusion, this store location has high quality items for good prices but I think I'll come back here only for Winners products and stick with other Home Sense locations when I specifically need stuff for our place. read more

The space is smaller than other Winners because it shares a section with Homesense. That being said, the department is smaller and consequentially, limited selection. The Winner's section is nothing to write home about, it has your usual gear for men. The Homesense section is, in my opinion, better. With items here that you can't find anywhere else (and I've been to a lot of Homesense's lately). Prices always seem reasonable for home decor, until I remember that most decor don't have any functional use. read more

I think this store gets a better shipment of high end name brands than the one at College. Come here if you are looking for higher end clothing. read more

I'm a Winners advocate. Always have been, always will. I do like this location because they usually have some awesome bags. But like any Winners, you must go frequent and with no expectations to be surprised. If you're in the neighborhood, pop in and see if anything catches your fancy. read more

I always like the cleanliness of this winners but they have cut down their runway section. It's still pretty good for jeans and tops but only a handful of dresses. Seems college now beats them for that section. I do like their men's sections here though as there's more selection and much more in regards to accessories for them here. This location k have yet to be lucky in the shoe department as o find more at the college location. Overall, the store spans over two floors and you are bound to leave with at least one item. read more

I got some earrings, a wallet that my Iphone can fit in and 3 pairs of shoes. That's if for a plus size girl like me. The clothing section was so pathetic that it shouldn't exist. Why bother wasting money on signage when there's no clothes?!! read more

Of all the Winners in the city, this or the one on Front are the best ones. I've gotten good jeans, shirts, t-shirts and cologne here at good prices. Bonus marks for the fact that it's in Yorkville without the boosted prices. Also, their sunglasses rack sometimes has Ray Bans and Oakley's. Staff is friendly. read more

With over two floors of discounted apparel and housewares, this Winners location on Bloor Street West at first doesn't fit the mold most stores on that street since it's not a high-end retailer. Smaller than the sister store at 444 Yonge, this Winners locations has a wide range of apparel, linens, and other housewares that are readily on stock. Store is kept in great order and the prices can't be beat. Purchased a pair of Calvin Klein king-size pillowcases for only $14 (originally $50) which is a steal here in Canada. Best time to shop is on Friday afternoons when new merchandise is being put out for the weekend shopping crowd. Recommended! read more

Everytime I'm in Yorkville I make a stop at this Winners location to find Runway deals for designer labels. Sometimes it's a hit or miss but that's Winners for you. However, when you find a hit for high end items at low end prices then you will be a happy shopper. read more

Good place to shop brand name stuff with discount price. But not all the time you could find it, you have to go there quite often to check them all. read more