I'm a Former Madewell Employee, and These Are the 6 Deals Worth Shopping From Its Loyalty Sale

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I'm a Former Madewell Employee, and These Are TK Deals Worth Shopping From Its Loyalty Event
Photo: Madewell/ InStyle

As a former Madewell employee, I know that the two best times of the year to stock up on the brand's new releases and customer-favorite essentials is the semi-annual Insider Event. This customer loyalty sale rivals Black Friday, with 25 percent off the entire store. But unlike Black Friday, it's not a one-day event. Deals last until September 26, giving you ample time to finetune your cart. To shop the sale, you need a Madewell account, and luckily, you can get one simply by registering and providing an email address — no previous purchase necessary.

If you're looking for some inspiration, or perhaps a little advice from someone who worked with the products daily, I've rounded up all of the on-sale items I'm buying (and some I'm restocking). From fall-ready knits to this year's It bag, here are the six Madewell items I'll be adding to cart during the brand's Insider Event.

Madewell Deals Worth Shopping
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The Perfect Vintage Straight Jean in Mayfield Wash

If you're looking to retire your skinny jeans but aren't quite ready for something super wide leg or slouchy, Madewell's Perfect Vintage Straight Jean finds a great middle ground. This pair is 99 percent cotton, which I tend to lean towards when shopping Madewell's collection. I've found that the cotton jeans tend to last longer and fit better, as the material can be broken in to fit your proportions. Former employee tip: If you have a pair of jeans you're no longer wearing, bring them into the store where you can trade them in for a discount on a new pair of jeans.

Shop now: $96 (Originally $128); madewell.com

Madewell Deals Worth Shopping
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The Western Ankle Boot in Leather

The leather shoes from Madewell are, in my opinion, unbeatable. For leather, the prices aren't outrageous, and the comfort is unparalleled. During this Insider Event, I'm planning to grab a pair of Western Ankle Boots, which combine the much-loved fall favorite with the Cowboy boot trend. As one reviewer noted, "[I] could not have asked for more in a new bootie for the fall."

Shop now: $149 (Originally $198); madewell.com

Madewell Deals Worth Shopping
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Signature Coverall Jumpsuit

I bought this jumpsuit three years ago and it's still in my rotation — due in part to the compliments I receive every time I wear it, but also due to just the sheer simplicity of it. This jumpsuit is cool enough on its own that you don't have to put too much thought into the rest of your outfit, and it pairs well with everything from sneakers to mules. Plus, I love that the buttons at the waist allow you to adjust this jumpsuit to best fit your figure. I have this style in a burnt red and am excited to add Smoky Grape, a faded purple shade, to my collection. If you're hesitant to buy a jumpsuit because of the fit, Madewell also has a similar style in curvy.

Shop now: $111 (Originally $148); madewell.com

Madewell Deals Worth Shopping
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The Sydney Hobo Bag

Similar to the shoes, I'm always gravitating towards Madewell's leather bags. They stand the test of time (i.e. the one I bought my mom while I worked there years ago remains her go-to bag) and they tend to stick to designs that won't be "out" by the next trend cycle. This sale, I'm opting for the brand's Hobo Bag, one of this year's hottest styles. It's simple and carries just enough for everyday use while the Burnished Caramel color is timeless and versatile.

Shop now: $89 (Originally $118); madewell.com

Madewell Deals Worth Shopping
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(Re)sourced Cashmere Sweater in Stripe

When Madewell puts its cashmere on sale, you buy it. This material is often not included in the brand's other sales — even those that are knitwear specific. I love that the (Re)sourced Cashmere Sweater in Stripe is made of recycled cashmere sourced from certified farms. Not that shopping doesn't always feel good, but it feels particularly great when you can do it more ethically.

Shop now: $141 (Originally $188); madewell.com

Madewell Deals Worth Shopping
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Airpuff Quilted Packable Puffer Jacket

The last thing I'm adding to my cart is the Airpuff Quilted Packable Puffer Jacket in Tundra. I own one of the brand's other packable puffers and have found that it's the ideal jacket for travel. It keeps you warm without being overly heavy and, when you're not using the jacket, it can be packed into a neck pillow — meaning one less thing you have stuff in your carry on. I love that this style has a hood (which is missing from the style I own) for those colder, wetter days.

Shop now: $119 (Originally $158); madewell.com

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