OK I’m new to the Black Friday game (foreigner here) Madewell has a -25% on their website now is it worth waiting for Black Friday or will it not get better than that?

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Here is my experience - Black Friday sales for clothes are mostly a sham. If you really want a great deal - wait till AFTER Christmas and early new year, that’s when most brands want to get rid of their old stuff and bring new stuff in. I’ve gotten the most insane deals during that time!
Typically, deals in store will be better than deals online because they have single items left in different stores - so you may need to spend time hunting, but boy - it’s always the best time to buy for me :)

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This. Black Friday isn't what it used to be. Now you also have cyber Monday and I think Green something. I find that you have to find a very specific deal on specific items and know when the timeframe is right for that retailer. At the end of the day if you know what the general price is over the year and think you're getting a good deal, go for it. I find it less of a hassle to return things than to constantly hunt down deals to save an extra $10.

I have free returns through ShopRunner through AMEX.
PayPal reimburses up to $60 or so on return shipping if you pay with PayPal option.
Many stores have holiday specials with returns up until end of Jan if you do find a better deal.
There are also price alert apps like Paribus

For most of those brands (madewell, banana, Ann Taylor, jcrew) I hold out for 40%.

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I think it’s 30 percent right now, but I feel like they run this sales quite frequently throughout the year. So there is no rush to buy it now because they’ll end up having another! But I do believe 30 percent is the most they will do.

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My citi card has price rewind. So usually I just buy whatever I want, keep the receipt, and check to see if prices drop.

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