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My Favorite Madewell Fall (& Winter) Finds with try-on pictures

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I am so impressed with the fall arrivals at Madewell right now. It’s hard for Madewell to let me down in general (they make my favorite white jeans EVER), but this year’s fall selection is by far the best I’ve see in a few years! The sweaters are buttery soft and so flattering, the shoes are GORGEOUS and fit right out of the box, and they also made the most stunning shoulder tote I’ve ever seen.

I’ve placed two large orders already this season! One order arrived earlier this fall and I’m currently awaiting the second order. Since I don’t have the second package yet, I’m don’t have photos to share of those pieces on myself, but I am sharing photos of my try-on from the first order. You’ll see all of the finds below!

Note: I am 21 weeks pregnant in the photos from order #1 and everything I ordered fit my bump just fine. Only one piece (this dress) has gotten too small over the last month as my bump has grown, but the rest still fit perfectly and I expect they will for some time.

Let’s jump right in.

My Favorite Madewell Fall Finds

I have a video on YouTube showing my favorite Madewell fall pieces or you can watch it below!

Sweaters and Tops

Ribbed Long Sweater Vest

This cream ribbed sweater vest is the SUCH a great fall find. It has a great relaxed fit that works with my 21 week baby bump, and the cotton material is SO soft. I can’t stand an itchy sweater, and this isn’t itchy at all. Not only does this sweater work well untucked (and with a bump!), but the side slits make it easy to front tuck as well, which is a flattering look and on-trend look, if you aren’t wearing over-the-bump maternity jeans.

(Re)sponsible Cashmere Oversized Crewneck Sweater

I wish that I could wear cashmere every single day. There’s just nothing like it. Madewell’s (Re)sponsible cashmere oversized sweater is oversized and slouchy, super soft, and comes in 5 colors. I went with Heather Seashell because it’s a neutral that I can style a million ways.

I wish I had a winter beach trip planned this year because I feel like I could be in a Nancy Meyers movie! I actually loved this sweater so much that I ordered a second color (which goes against my own styling rule of not having two of the same item) so that I can wear it more often. I’m waiting on the Hthr Pyrite color-way to arrive.

Brushed V-Neck Cardigan Sweater

I ordered this brushed cardgian a week ago and cannot wait for it to arrive. While I rarely go for a sweater that’s cropped while I’m pregnant, I thought this might look cute with a white tank underneath if I left the cardigan unbuttoned. The fabric looks soft and cozy.

Cable-Knit V-Neck Sweater Vest

I loved my green sweater vest from Madewell last year, so I had to try this v-neck version. Again, it hasn’t arrived yet, but I have very high hopes. I find that sleeveless sweaters are the BEST for the warmer fall months when you’d like to dress for fall but it it’s too hot for a long sleeve top by the afternoon.

Rugby Stripe Polo Sweater

This rugby stripe polo sweater is a little bit sportier than the rest of the items in this haul, but I absolutely love it. The dark blue and navy combo is perfect for the fall, and the material is incredibly soft. I just refuse to wear sweaters that make me itch, especially when Madewell has so many good ones. This sweater is made of a blend of polyamide, merino wool, polyester, and alpaca. It’d be cute with denim shorts as well, if you’re living through Fake Fall.

Modular Oversized Button-Up Shirt in Mixed Stripe

I have a feeling this oversized button down is going to be tres chic with a bump. I’m going to style it with my favorite white maternity jeans.

Crinkled Button-Up Shirt

And while we’re on the stripes train, I added this crinkled button up to my order as well. I’m not sure if I’ll wear both, so I’m excited to try them both on with jeans once they arrive. A button down is such a GREAT everyday shirt for cooler weather. It’s not too hot, not too cold, and totally appropriate for fall.

Shawl-Collar Cardigan Sweater

The last sweater I ordered was this shawl-collar cardigan. I like the length for cozy outfits at home, and it’s also nice that you could wear it with jeans as a polished outfit.


Boiled Wool Sweater Blazer

This wool sweater blazer could fall under jackets or sweaters, but since I only got this one outerlayer, I decided it should go in the sweater section. I LOVE the fit of this grandpa cardigan. It’s the perfect weight for layering over simple outfits, and takes your tshirt and jeans look to a different level. If you work in an office, this would be ideal for those months when it’s too cold to take off your jacket.

The Bedford Oversized Belted Blazer in Plaid Wool Blend

Ummm HELLO gorgeous. I love this belted blazer so much. A blazer is already one if my favorite articles of clothing, but when it’s belted, it’s even more flattering. I love the weighty wool plaid and the padded shoulders. It has a somewhat dressy feel too it, but it would also be super cool styled with black jeans and Converse sneakers. I really hope it works well with my bump.

The Larsen Blazer in Mixed Plaid

I got another blazer (I know, I know). But I couldn’t get over the Larsen Blazer in the fun mixed plaid. It’s a little more “fun” and out-there than something I might normally wear, but because it’s a blazer, which is naturally super polished, I love the combo. I would wear this blazer as the main statement of my outfit and style it with solid colored pants and tops. Probably black jeans!

The Gianna Coat in Insuluxe Fabric

Can you EVEN with this coat. I think this is the item I’m most excited for in my second order. The chocolaty brown color, the thick wool material, the length, all of it. I’m in love. A dressy wool coat is a closet staple I have no problem investing in. The relaxed style is my favorite these days because it can be easily dressed down. It will look great leggings and a black sweatshirt underneath, inspired by this look.


Cable-Knit Oversized Mini Sweater Dress

I LOVE this oversized cable-knit sweater dress. It’s the perfect size for a growing bump, but it’s not maternity specific, which is a win-win. I love when I can wear something after having my baby too! The knit design is super fun and different with the various stitching and it can be styled with loafers, boots, booties, or clogs.

Annamarie Mini Dress in Lunar Wash Denim

This black mini dress is another great everyday fall dress. I love that it’s a denim blend because it feels super casual. If you have a fall concert coming up, this would be great option to wear with boots, but you could also style it for everyday life with loafers, clogs, sneakers, or booties. It’s also bump friendly, as you can see below. The back has a small keyhole and then buttons up, which is cute but doesn’t feel too revealing for everyday wear.

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Unfortunately it’s a little too small on my bump and bust a month later!

Ribbed Midi Sweater Dress

I only picked out one dress for my second order, but I am SO excited about this Ribbed Midi Sweater Dress. The stripes are great fall colors, the length is great for cooler weather, and the material is going to be perfect over a bump. Comfortable, but still cute and on-trend dresses are a challenge to find while pregnant, and this one is a knock out.

Mini Shirtdress

It’s hard to beat a classic shirt dress like this green one from Madewell. The color is right on par for fall, and the style is super relaxed and boxy which is ideal for a bump. I didn’t end up keeping this in my cart because I needed to take a few things out, but I wish I had gotten it! It would be perfect with clogs.


The jeans I ordered aren’t going to be helpful for everyone since they’re maternity, but they are TOO GOOD not to share! If you’re pregnant, you’ve got to try Madewell’s maternity jeans. The fit is amazing, and I love that I’m able to wear polished outfits for the fall and winter rather than sweatpants or leggings everyday (even though I’d rather be in loungewear most days if we’re honest).

Maternity Over-The-Belly High-Rise Skinny Jeans in Smithley Wash

First things first, a good pair of skinny jeans. These over-the-belly skinny jeans from Madewell are the perfect classic wash, have a great belly band, and look SO good! The only note I have is that this pair runs just a tad big, so size down one size. I ordered a 25 and could have done a 24.

Maternity Over-the-Belly Perfect Vintage Straight Jean in Tile White

This pair of maternity straight white jeans, however, fit like a GLOVE. I already loved their non-maternity white jeans, and these are just as great. It’s fun to find a pair of maternity jeans that aren’t a skinny style. I got a 25, which is my usual pre-pregnancy size in Madewell jeans and they fit perfectly.


One of the biggest wins from Madewell this fall is their shoe selection. The styles are cute and classic, which is obviously important, but the fit/feel is just as good.

The Drumgold Boot in Extended Calf

I got rid of all of my riding boots a few years ago because I wasn’t a big fan of the buckles or details on them, so finding this simple pair of tall fall boots got me SO excited. They’re sleek and polished, but great for everyday because they aren’t heeled. I love the versatile brown leather and the inside zip for easy on-and-offs.

The Monterey Tall Boot

I got the monterey tall boot in black because I wanted my heeled pair of booties to be a bit dressier. The fit of these was just as good as the pair above! They have a full zipper on the inside of the calf, so they are easy to slide on and off. They feel great immediately once your foot is in them, are easy to walk in and don’t feel heavy. They run true to size (I always go up 1/2 size in boots). I love the short block heel because it’s easy to dress up or down.

The Essex Ankle Boot

Everyone needs a classic black ankle boot with a block heel. I’ll wear these with dresses and jeans all throughout the winter.

The Janeen Platform Mule

Everyone needs a platform clog in their closet this fall. I got a great pair last year and I wore them into the ground, so the Janeen platform mule is going to be this year’s replacement and the quality makes me believe it will last for years. I find that clogs are super versatile for when you just aren’t sure what shoe your outfit needs…the answer is probably heeled clogs. The fit is true to size.

The Lacey Ballet Loafer

I was totally blown away when I put this pair of Lacey Ballet Loafers on. They feel like they’ve already been broken in! It’s amazing. The black color is perfect for a corporate office, and the 0.5″ heel height is ideal for wearing all day.

The Lawrence d’Orsay Flat

If you’re looking for the perfect work flat, I found it. The Lawrence d’Orsay Flat is SO flattering and feminine. I love the shape of the top and the square toe, but the real selling point is the MWL Cloudlift Lite padding. It’s SO comfortable. I would say to size down since my usual size 6.5 slips off my foot, so I’m exchanging them for a 6.


The Essential Bucket Tote

This might be my favorite find from this entire order: The Essential Bucket Tote. It’s BEAUTIFUL. The chocolatey brown color is gorgeous in person, the shoulder strap has such a chic buckle, and the size is big enough to fit a laptop. It’s truly STUNNING. I might go ahead and add it to your Christmas list if I were you! I’m taking it on my upcoming work trip!

The Essential Mini Bucket Tote

Because I loved the larger version (above) so much, I decided I may as well try this smaller crossbody style (but in a fun color). I went for the Chocolate Raisin colorway. This would make a great Christmas gift!

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