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My Top 12 Madewell Insider Sale Picks!

Sep 17, 2021

Madewell Vintage jeans | Madewell Insider Sale

Above: Vintage jeans in Fitzgerald wash, part of the Madewell Insider sale! Details below. (Cardigan is Madewell from last year, sadly they didn’t come out with it again this year!) 

I have to admit, I have been very reticent to acknowledge that fall is upon us. September happens to be my favorite month of the year, but the end of summer always makes me sad because I know winter will be here before we know it! (Not that I don’t like winter, I do–I just don’t like 6 months of winter like we get here in Chicago.)

One silver lining though is that fall clothes are really fun to shop for, and even more fun to wear! Madewell is one of my favorite spots to shop for fall/winter essentials, and right now, they’re having a 20% off for Madewell Insiders sale! (All you have to do is sign up for their email list to become an insider!) If you’re in the market for some new fall staples, I’m rounding up my picks below!

My Madewell Insider Sale Picks:

Shirt jacket: 20% off for insiders!

Also known as the “shacket” but I’m unsure about that term. This is one of the items you all were most excited to wear this fall when I polled you on Instagram stories! This one has a cabin-chic 90’s vibe and I’m into it. Will look so cute styled with the vintage jeans and lace-up boots (also on sale!) linked below!


Perfect Vintage Jeans: 20% off!

What I’m wearing in the photo above! I love these jeans that I bought last year! As the name would suggest, they have that perfect lived-in, vintage feel. They hug you in all the right spots and make your butt look great!

Sizing: These will feel like they run VERY VERY small at first. But they will stretch and mold to your body! I got my normal “pandemic” (pre pregnancy) size which is a 26 and they stretched out to be the perfect fit for “out in public” jeans or “wearing for a few hours” jeans. But if I wanted them to be like, “wear at home for 12 hours jeans” I would’ve gone up a size! (I’m 5’6 for height reference).

Lace up booties: 20% off!

I have last year’s version of these boots and I absolutely love them. This year’s version comes with a lug sole, which as you probably know, is an “all the rage” trend right now. I’m not huge on trends, but I am big on practicality–and let me tell you, there’s nothing more practical for a midwestern winter than a lug sole. The best traction! If lug soles aren’t your thing, this pair is basically the same shoe, just a regular sole!


Packable quilted puffer pullover: 20% off!

Definitely giving me Barbour vibes at a much lower price! A packable jacket is a staple in every fall wardrobe, especially for weekend getaways and vacations! The great extra layer for in-between better that can be easily stuffed away in your bag!

Plaid blazer: 20% off!

Plaid blazers were another item you all were super excited to wear this fall! I tend to prefer a boyfriend cut with a chunky texture, and this one fits the bill! It will also look really cute styled with cutoff jean shorts for in-between weather!


Donegal henley sweater: 20% off!

I LOVE me a donegal sweater. I also love me a henley sweater. This is the best of both worlds! Has that apres ski vibe that I can never get enough of. Perfect for wearing with leggings around the house or paired with jeans and booties for a cute/casual look.

Low heeled riding boot: 20% off!

A riding boot is a classic that never goes out of style, and I especially love the height of the heel on this one! Probably the most versatile style of riding boot you can find, because the heel is low enough for logging tons of mileage, but it’s a bit more elevated/sophisticated with the heel, meaning you can dress it up for a nice dinner and not feel too casual! This is also a REALLY good price for a quality pair of leather boots!


Ruffle neck sweater: 20% off! 

So glad this bestseller is back! I have a lighter beige color from last year, but loving the new colors, especially this hue that is perfect for fall! It runs TTS! I love the feminine ruffle detail. It’s casual, but feels extra special so it’s great for wearing out to dinner!

Striped sweater:  20% off!

A classic, with a twist! Love the chunky knit and relaxed look of this one! Stripes make every outfit more fun.

Puff sleeve top: 20% off! 

I feel like finding pretty fall/winter tops to dress up and wear out can often be a challenge! This one is perfect–you can never go wrong with a black top! I love the statement sleeves and super chic square neckline. Comes in a pretty eggshell color, too!

Gauzy button-down: 20% off! 

I am in love with a good soft gauzy button down, and it’s one of my favorite summer staples. I love that these come in the most beautiful fall colors! The dusty rose especially. This will be a great layering essential!

Classic skinny jeans: 20% off! 

I have been getting asked, “are skinny jeans still cool?!” a lot lately, and the answer is–YES. They absolutely still have a place in your wardrobe. I typically only wear skinny jeans in the winter, and that’s because no other cut of jeans looks good tucked into boots! I especially love a classic, dark pair. Madewell skinnies have been a GG reader favorite for YEARS.

Smocked gingham dress: 20% off! 

Same style of dress we’ve all been living in this summer, but with a pattern and color perfect for fall! Such a pretty and flattering fit, and will look so cute with fall boots and booties, jean jackets, sweaters–you name it!

Hope you have a wonderful weekend!

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