I am a believer in owning your personal style, saying what you mean, asking for what you want, living authentically and the power of simplicity — in fashion, and in life.

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10 Rules for Effortless, Everyday Style

In this series, I share some simple tips for leveling up your daily looks.

First things first — THEIR LEATHER JACKET IS INCLUDED!! Run, don’t walk — if you’ve been thinking about it, now is the time. They hardly ever discount this jacket!!! It’s timeless and cool and never goes out of style. Thinking about the dried cedar color? I did a whole blog post on it back in 2019 — check it out here!

To access the sale, you need to be part of their Insiders program, which is free and only requires an email address. All Insiders can get 20% off pretty much everything at Madewell, and Stars and Icons get 25% off.

Here are the rest of my picks from the sale…

Leather Pants | I have an older version of these and love them. You can see me wearing them here and here.

Leather Heeled Mules | These are really comfortable and not too high. I have them in brown!

Skimmer Mules | These amber brown ones and the vintage canvas ones are my favorite colorways in this style. Great comfortable shoe option for spring!

Flap Crossbody | I have this in black — carry it as a crossbody, by the top handle or as a clutch (both straps are removable).

Classic Denim Jacket | This one is my go-to denim jacket! I recommend sizing up if you can — it does run a bit small. Available in sizes XXS-3X

White Courier Shirt | I’ve had mine for years and it’s still one of my favorite tops — great fabric, not too sheer and can be worn with so many different things!

Medium Transport Tote | This is a great tote that’s sturdy and holds up well over time. I recommend a monogram to add a personal touch. I love the large stamping in metallic gold (and that’s what I have on my tote).

Raw Hem Perfect Vintage Jeans | I tried these on in my local store in December and absolutely loved them! The hem is super cool and they fit really well. Size down 1-2 sizes.

Worn In Perfect Vintage Jeans | I could see these really getting better and better over time, especially as the knee gets fully busted out. In general, I tend to size down from my Madewell skinny jean size when it comes to the Perfect Vintage styles.

Double Breasted Blazer | All three colors are perfection! This is the easiest WFH layer, too. Pair with jeans and a cami or tee and you’re set for your Zoom calls.

Floral Midi Dress | Pair this with sneakers and a leather jacket and you’re set! Perfect mix of masculine and feminine, plus also happens to be a super mom-friendly outfit. If you’re looking for a dress with more color, this one is really beautiful, too!

Square Neck Blouse | An ideal spring and summer top — I’d pair this with straight leg jeans and mules (surprise, surprise). Looking for something in black? I adore this short sleeve blouse and would style it the same. Love pattern? Check out this one.

Baseball Cap | I have a similar off white one from years ago and it’s still the only hat I ever wear. Ideal for hiding dirty hair and keeping the sun out of your eyes (and off your beautiful face!)

Balloon Sleeve Top | The color and shape of this is so fun! I’d tuck it into high rise jeans or denim cutoffs. It would look great with white denim, too!

Green Grandpa Cardigan | The stitching is so beautiful and the green would be a beautiful dose of color to add to a neutral wardrobe.

Knotted Crossbody | This is a cute little crossbody bag for running errands — make it even cuter with a metallic gold monogram!

Tigerized Cropped Cardigan | I love, love, love this cardigan!! I tried this on in December, too, and recommend going down 2 sizes if you want to wear it like a top vs. a cardigan.

Are you shopping the sale? Do you need help finding anything specific — let me know in the comments and I’d be happy to help you out!

Shop the Sale

Madewell Insiders Event Picks

Read the Comments +

  1. Jen says:

    Finally scooping up this leather jacket!! Thanks for the recommendation.

  2. Courtney says:

    Looking for some cute tops to wear during early pregnancy. Thanks!

  3. Jazmin says:

    I love my leather jacket from Madewell! Do you have any tips on how to care for it? The edges of my sleeves are peeling a little bit. Thank you 🙂

    • Natalie says:

      Oh oh! That hasn’t happened to mine. I don’t do anything to care for mine currently but now I’m wondering if I should be conditioning or something. May need to do a little research on that. This is the first leather jacket I’ve ever loved enough to actually wear regularly.

  4. Jessica says:

    I just got hired at a new job in social services! I am so excited but none of my work pants fit. I’m looking for not to dressy but not too casual picks. I am a curvy woman. I appreciate all your suggestions. Thanks so much

  5. Autumn says:

    I love Madewell! I’ve been trying to decide on a straight or boyfriend style jean for my smaller frame! I just realized this week I probably need to be buying petite sizes, since I am on the shorter side. And I love that they have curvy options, because I always get a gap in the back of my jeans. I also really love the vintage 90’s style jeans, but I’m afraid of trying such a thick, unforgiving material. Do you have any suggestions for a straight jean on a curvy, petite frame? Thank you in advance!! Xoxo

  6. JH says:

    I’m looking for a crisp white button down – long enough to over my backside in leggings – but also a layering piece 🙂 would the short sleeve one here work or should i look for a long sleeve? Loved the Jenni Kayne boyfriend but looking for a bit lower price point.

    • Natalie says:

      I love the Courier Shirt so much, but if you really want a good layering shirt I think the sleeves might end up frustrating you. I can layer it with certain things, but it’s not quite as versatile layering-wise than a long sleeved one would me.

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Hi, I'm Natalie

I am a believer in owning your personal style, saying what you mean, asking for what you want, living authentically and the power of simplicity — in fashion, and in life.

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