I have scored some excellent pieces at unbelievable prices at Winners– think J Brand jeans for $30; Mackage overcoat for $80; and my favorite Diane von Furstenberg 3-piece luggage set for $120 – and every time I share these successful finds with friends and family, they always say, “That’s amazing! How do you find these deals? I can never find anything in those stores!”

I think back to the countless trips I’ve made to a Winners or Marshalls with my boyfriend, only to have him wander around and then eventually follow me around the store because he can’t find anything. Looking back, I realize it’s because he doesn’t know how to shop the store. In his defense, it can be a really overwhelming, daunting place if you don’t know how to optimize your trip! I’m sure he’s not alone in this, which is why I’ve decided to share 5 tips on how to join me in the Winners’ Circle:

  1. Give yourself time! 


I can spend hours perusing every single rack. You can’t shop in a rush and expect to find the deals. They’re called “hidden gems” for a reason. I like to go during quieter hours/days such as Wednesday/Thursday evenings when the store has just recovered from the weekend and is being prepped/refreshed for the upcoming weekend.

2. Know yourself.

Yeah, that’s the title of a Drake song, but I mean it! You should be well aware of what would/wouldn’t look good on you just by quickly glancing at the hanger. When I’m at Winners, I am literally sorting through each hanger on the rack. It takes me a good 5 seconds to look at a piece and decide if it’s right for me. Of course, you sometimes want to try a new trend/silhouette, but are a little unsure. For those instances, try it on! You can bring up to 10 items to the fitting room or you can always return them if they don’t work out with your wardrobe, just be cognizant of the return policy.

3. Shop with purpose, but be open-minded.

Always have a vague idea of what you hope to find (a new blazer for work, a dress for an event, a pair of heels for a party etc.), but don’t get too specific. Think of the necessities – colour options/silhouette, but visualizing something specific will lead to disappointment. Being open-minded always leads to pleasant surprises and finding pieces that you wouldn’t have noticed with tunnel vision.

4. Always check the clearance section first.

The beauty about Winners is that they don’t follow the typical seasonal timeline that most retailers do. They don’t really have standard “End of Season Sales,” which means you can find seasonally-appropriate pieces on clearance and wear them right away.

5. Rank your favorite departments and shop them in that order.


I always visit 1) shoes, 2) clothing, 3) handbags. Why? Because that’s how I’d rank my favorite pieces. Why risk letting others find the deals in your favorite departments first? Finders keepers! Think the Sample Sale scene from Confessions of a Shopaholic.

Trust me, you do not want to miss your chance.

Have any deal-finding tips you’d like to share? I’d love to hear from you!


One thought on “THE WINNER’S CIRCLE

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