OOTD: My September 2019 Madewell Insiders Promo Picks

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OOTD: My September 2019 Madewell Insiders Promo Picks :: Effortlessly with Roxy

Ahhh, Madewell. Lovely, lovely, Madewell. It’s my favorite brand these last couple of years. Right now there’s an extra good reason to love Madewell! That’s because it’s time for their loyalty program special promo. If you’re a Madewell Insider (it’s free!!) you can take 15% off your purchase through next Wednesday. Picks? I have lots of them. Keep scrolling for my September 2019 Madewell Insiders Promo Picks.

OOTD: My September 2019 Madewell Insiders Promo Picks :: Effortlessly with Roxy
OOTD: My September 2019 Madewell Insiders Promo Picks :: Effortlessly with Roxy
OOTD: My September 2019 Madewell Insiders Promo Picks :: Effortlessly with Roxy
OOTD: My September 2019 Madewell Insiders Promo Picks :: Effortlessly with Roxy
OOTD: My September 2019 Madewell Insiders Promo Picks :: Effortlessly with Roxy
OOTD: My September 2019 Madewell Insiders Promo Picks :: Effortlessly with Roxy
OOTD: My September 2019 Madewell Insiders Promo Picks :: Effortlessly with Roxy

Let’s begin with the outfit I’m wearing, shall we? Everything Madewell I’m wearing (which is pretty much everything except my watch and hair clips) are part of the September 2019 Madewell Insiders Promo. Below are my outfit details.


I added a jacket — specifically, the Washed Leather Motorcycle Jacket, which is usually excluded from Madewell’s promos but miraculously made the cut for this promo! (That’s subject to Madewell discovering this and changing their minds, so hurry if you want that jacket!!) I own the jacket in two colors — oxblood, which is no longer sold, and burnt sienna, which you can grab right now. This jacket is so buttery, wears so well, and is endlessly flattering! If you follow my liketoknow.it profile, you can see a photo of me in this top outfit with the jacket added.

I expect this outfit to be a mainstay for me throughout Fall and Winter. The Ribbed Knit Wrap Dress is so comfortable on! Zero itch factor and light enough to wear on warm days. I ordered both a large and a medium, expecting to keep the large. However, I found this dress to be super stretchy and by the end of the day the large was too big on me. So I returned it and kept the medium instead. The store SAs loved the dress so much one of them bought the large the moment I returned it! So I’d say this dress is very likely to sell out. This outfit comprises my top September 2019 Madewell Insiders Promo Picks. But I have more outfit ideas too!


I initially tried on this look to see if the Transport Camera Bag in dark cabernet would work with it. Ultimately I decided probably not (the English saddle color would work much better!). The Camera Bag is a great little crossbody that has a surprising amount of storage in it. It comes with a shoulder strap as well as a wider clip strap. I saw the latter strap being used to wear the bag around a mannequin’s waist in-store. Lots of possibilities!

The Rhyme Top doesn’t look like much online. Sometimes Madewell isn’t so good with their outfit ideas on their own website! In real life however I found the top to be beautiful on. Although it isn’t body-skimming at all, it really flattered my hourglass shape. The top is begging to be half-tucked into either a skirt or jeans.

I would probably finish this outfit with the Brooke Ankle Strap Heels shown in the outfit spread above. But because I know not everyone is into heels I’ve offered some additional shoe options in my September 2019 Madewell Insiders Promo Picks outfit #2.

OOTD: My September 2019 Madewell Insiders Promo Picks :: Effortlessly with Roxy

To be fair, I was 3/4 of the way inspired to create this outfit by Madewell’s own styling. Sometimes their website shows cute outfits after all! My September 2019 Madewell Insiders Promo Picks wouldn’t be complete without some cute sweaters. The Arden V-Neck Pullover Sweater absolutely fits that bill. Deliciously soft and made to be worn over all manner of things, I love the three colors it comes in. If you find it too short like the reviewers did, I’d point out the similar Thompson Pocket Pullover Sweater or the Brushed Rib Pleat-Sleeve Top. Both of those sweaters come in a similarly creamy color.

This outfit is crying for a tote bag, so I added two options from the Transport Collection. There is the traditional, classic, hard to beat Medium Transport Tote in English Saddle which will never go out of style. I also added a trendier option in the Medium Transport Tote: Corduroy Suede Edition in Boutique Gold. The latter will match the skirt’s flowers very well.


What’s better than a pretty polka dotted dress? In my September 2019 Madewell Insiders Promo Picks, the answer is a bubble cardigan to go with it!! This outfit embodies everything I love about Madewell. It starts with a cute, body-skimming dress with an a-line shape that flatters most everyone. The bubble cardigan is an ideal layering piece — loose, but with personality! It’s close to selling out on Madewell’s site, so I’ve linked to it at Nordstrom too. Right now Nordstrom is not price matching outright, but if you place your order and then call Customer Service for an adjustment they’ll very likely give it to you.

We also need to talk about the Jess Slingback Mule. They. Are. AMAZING!! Usually it takes me days to break in my shoes. I’ll wear them around the apartment for 45 minutes or so, then out to work for a few hours with a backup pair in case my feet start to hurt. With the Jess Slingback Mules, I ended up wearing them for 8 hours straight out of the box. They were comfy all day long! No break-in period needed which constitutes a shoe miracle for me. I’m wearing them in the outfit at the top of the post. I found them to run true to size.

OOTD: My September 2019 Madewell Insiders Promo Picks :: Effortlessly with Roxy

Does this final outfit idea from my September 2019 Madewell Insiders Promo Picks not scream Fall? Or at least say it quite clearly? Summer may not yet be officially over but there’s no harm in planning for the seasons ahead. The Thompson Pocket Pullover Sweater comes in three solid colors including the olive you see above. It’s also available in a rainbow stripe and a navy stripe on ivory. I found this sweater to run true to size. Drop sleeves and large pockets don’t often work on me, but this sweater is cute on! Because of my chest size (34DD) it’s shorter on me than on the model. It is not overly cropped though.

I adore the snake print on the Frances Loafer! In fact, I like it even better on the Regan Boot! The boot will be part of my September 2019 Madewell Insiders Promo Picks order. I also plan to order the Chain Crossbody Bag in Nubuck Leather. We’ll see what else makes it into my promo purchases!

Below, all of my September 2019 Madewell Insiders Promo Picks! What have you loved at Madewell lately?


  1. Rach DiMare
    September 6, 2019 / 9:44 am

    Madewell is the BEST! They take all my money haha! That wrap dress looks amazing on you and love that deep color!

    • September 8, 2019 / 2:37 pm

      Mine too! They get the majority of my clothing spending money these days. Thanks Rach!!

  2. September 6, 2019 / 11:02 am

    What a roundup! I absolutely love their classic style and their jeans have always been one of my faves.

    • September 8, 2019 / 2:37 pm

      Yes their jeans are rather magical. I've noticed Madewell's sister store J.Crew has started to pick up on this and their jeans are getting better too.

  3. anniewearsit
    September 6, 2019 / 11:39 am

    Madewell always has THE cutest fall clothing, and l love shopping there! Thank you for sharing your gorgeous selections!

    • September 8, 2019 / 2:56 pm

      Of course! Love rounding up their stuff. 🙂

  4. September 6, 2019 / 1:23 pm

    Madewell has some of the best pieces for all year long! That color looks beautiful on you!

    • September 8, 2019 / 2:56 pm

      Thank you! Red is such a great color for Fall.

  5. September 6, 2019 / 2:26 pm

    I am SO excited about this sale! TAKE ALL OF MY MONEY. Love your dress and your picks!

    • September 8, 2019 / 2:56 pm

      Haha I feel pretty much the same way.

  6. sylvs
    September 6, 2019 / 2:30 pm

    I love madewell as well. I wish it was fall already! it's 100 in California. ugh

    • September 8, 2019 / 2:57 pm

      Oh my goodness! It's still in the 80s here most days too. So I'm prepping, but not really wearing much Fall stuff yet.

  7. rebecca o
    September 6, 2019 / 2:57 pm

    ooooh i do love Madewell! need to check this out and get some staples for fall!

    • September 8, 2019 / 2:57 pm

      Let us know what you get!

  8. She Saw Style
    September 6, 2019 / 7:56 pm

    Uh oh – now I want it all. I've shockingly never shopped at Madwell, but I've wanted to for quite some time, so maybe now is the time to bite the bullet and stock up on my autumn wardrobe!

    • September 8, 2019 / 2:58 pm

      I think now is a great time because the Fall stuff is on discount!

  9. Zach & Julie Ruhl
    September 6, 2019 / 10:19 pm

    wow so many cute outfits in this post! I need you to come and be my stylist! lol Also I've been looking for a cute camera bag for a while now and I think I may have finally found it.

    • September 8, 2019 / 3:01 pm

      I'm totally flattered! You know we're planning an adventure van lifestyle in the next few years so maybe we'll come across you guys on the road!! We love your blog and Insta feed!!

  10. Christa Anne
    September 7, 2019 / 12:25 am

    I love Madewell! Their fall stuff is always so good. It might be time to do some shopping!

    • September 8, 2019 / 3:02 pm

      Fall is my favorite season anyway and yes Madewell does Fall especially well.

  11. acmade
    September 7, 2019 / 3:31 am

    I love madewell! Need to check out the sales!

    • September 8, 2019 / 3:02 pm

      Totally recommend that you do!

  12. September 7, 2019 / 12:31 pm

    I'm definitely in need of a fall wardrobe refresh and I'm loving all these Madewell picks. So many great fall tones and textures.

    • September 8, 2019 / 3:03 pm

      Agreed, I really like the color palette for their Fall collection.

  13. kelsinwonderland
    September 7, 2019 / 4:08 pm

    Absolutely adore those slingback mules!!! Madewell always has great sweaters, too. Really digging the fall tones and patterns this year.

    • September 8, 2019 / 3:03 pm

      Cannot say enough great things about the mules!!

  14. September 8, 2019 / 8:20 am

    I don't think I have anything from Madewell. They have so many cute things, I might have to do some shopping now!

    • September 8, 2019 / 3:04 pm

      They are pretty much my favorite store these days so I'd encourage anyone interested to try some stuff on!!

  15. gretahollar
    September 8, 2019 / 6:27 pm

    Madewell is one of my favorite stores so I'm so excited to shop these picks! So perfect for fall!

    • September 9, 2019 / 9:38 am

      Hooray for Fall shopping! My favorite season.

  16. September 10, 2019 / 4:24 pm

    I am loving ALL of these picks. Madewell always has cute stuff. This has me excited for fall weather!

    • September 11, 2019 / 4:44 pm

      Oh me too, for sure!

  17. Whitney
    September 11, 2019 / 1:23 pm

    Loving all of these fall items! This sale is always a favorite one to get ready for fall! Such cute shoes btw. The perfect color for fall!

    • September 11, 2019 / 4:44 pm

      Thanks Whitney!!

  18. Lindinha
    September 11, 2019 / 3:38 pm

    Just came out of Madewell and saw all the new fall pieces. Very happy with the styles and prices and looking forward to getting one of those bobble cardigans!

    • September 11, 2019 / 4:44 pm

      Awesome Lindinha! We can be cardigan twins. =)

  19. September 13, 2019 / 5:26 pm

    Ohhhh – great picks, Roxy! I bought the Emmet Wide-leg Crops in black. I am losing my mind with all these wide leg cropped styles and now want the jeans you showed in the Hayes wash. SO cute! This style better stick around for a long while since I've bought so much of it! lololol

    • September 14, 2019 / 3:03 pm

      Thanks Cynthia! Yes I like wide leg pants too and given what I just saw on the NYFW runways, it's a trend that will be around for a little while. =)

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