It’s my favorite season and my favorite store. Does it get any better? Get ready for everything from new jeans to jackets and sweaters and more in our Madewell Fall try on!

Madewell Fall Try On Haul

My Sizing

For reference, I’m 5’7 1/2″ with a short torso and very long legs! I typically wear a 29 in jeans or a size 8. My bra size is a 36C, and I typically wear a size medium (or 8) top. 

If you ever have any question about what size I’m wearing, check the links below each image! I list any recommendations I have for sizing up or down for quick reference. (TTS= true to size!) For full details, I’ll be chatting all about quality, style, and fit in the paragraphs above each photo. Let’s go!

Corduroy Shacket + Perfect Vintage Straight Leg Jeans + Lug Sole Boot

Hello, this is my new fall signature outfit. I love this corduroy shacket so much. It’s super-soft, flexible, and can be worn open or buttoned up as a shirt (hence shirt + jacket = shacket 😉)! The color is also just beautiful in person. It’s such a rich golden caramel. But if this isn’t your ideal color, it also comes in a soft pink, faded green, and a creamy white. Size down one. I’m in the small with plenty of space for layering.

Let’s chat the jeans. They’re an update to one of my all-time favorite denim cuts: the Perfect Vintage Jean. Instead of having a more tapered cut like the original PVJ, these are more of a true straight leg with a relaxed fit through the thigh and calf. They still have a super-high 11 1/4″ rise with a ripped knee. I’m in the 28 regular length.

The lug sole boots are technically not new but since they’re a fall staple, and Madewell brought them back, I had to call them out. I love the lug sole and rich brown leather. They do fit TTS, and look great with straight leg denim!

Henley Sweater + Perfect Vintage Straight Leg Jeans + Lug Sole Boot

This sweater is one of my favorite purchases of this order. I love the henley detail, the brown and black speckles in the yarn, and the relaxed fit. It’s giving me borrowed-from-the-boys vibes that I’m here for. The fit is relaxed but I stayed TTS and like the fit.

Let’s chat the jeans. They’re an update to one of my all-time favorite denim cuts: the Perfect Vintage Jean. Instead of having a more tapered cut like the original PVJ, these are more of a true straight leg with a relaxed fit through the thigh and calf. They still have a super-high 11 1/4″ rise with a ripped knee. I’m in the 28 regular length.

The lug sole boots are technically not new but since they’re a fall staple, and Madewell brought them back, I had to call them out. I love the lug sole and rich brown leather. They do fit TTS, and look great with straight leg denim!

Boyfriend Plaid Top

Although it appears more white online, the background of this plaid top is more yellow-y. I still love the color combination with the rust and black windowpane plaid! Fit is boyfriend-style, a split hem, and extra length in the back. I stuck with my true size, and while it’s oversized, it’s perfect for wearing with a slimmer leg jean (see outfit on the right!) or with leggings. If you plan on tucking more, I’d recommend sizing down one.

Quilted Swing Top + Classic Straight Leg Jeans

I’m a sucker for a white top, especially if it has ladylike details like this one! The bib is quilted with three buttons, and the fabric has a natural crinkle to it. The sleeves are also blouse-y, as is the fit through the body. This top is perfect for both the office and the weekend. I’m in my true size medium.

The jeans are the Classic Straight Leg Jean, and unlike the other pair I tried on, they are a little more slim through the leg. They have the same 11 1/4″ high rise and 99% cotton 1% elastane construction but still felt stiffer than the previous pair. I sized down one to a 28 (as I typically do in Madewell denim), but these were too tight in the waist. I’d recommend staying with your true denim size (for me a 29/8).

I’ve been wearing these mules for years, but they’re a classic, so they had to make an appearance. They are consistently one of my most-worn shoes in fall. I recommend sizing up 1/2 size. They also come in black.

Polo Sweater + Classic Straight Leg Jeans

I’m kinda digging the preppy vibes that are big this fall. It brings me back to my middle school days. Does that age me?! 😂 This sweater is also giving me a bit of a menswear feel with the tipped polo collar. Fit is cropped, wide, and boxy but I’m sticking with my true size medium. It also comes in solid versions without the stripes. Be warned: it does have wool if you’re sensitive! But I did not find it itchy or uncomfortable.

The jeans are the Classic Straight Leg Jean, and unlike the other pair I tried on, they are a little more slim through the leg. They have the same 11 1/4″ high rise and 99% cotton 1% elastane construction but still felt stiffer than the previous pair. I sized down one to a 28 (as I typically do in Madewell denim), but these were too tight in the waist. I’d recommend staying with your true denim size (for me a 29/8).

I’ve been wearing these mules for years, but they’re a classic, so they had to make an appearance. They are consistently one of my most-worn shoes in fall. I recommend sizing up 1/2 size. They also come in black.

Quilted Shirt Jacket + Classic Straight Leg Jeans

On the shirt vs. jacket range, this one is definitely more of a jacket! It’s fully lined with both interior and exterior pockets. But it still has the oversized shirt-style cut with shirt-tail hem. I sized down one and like the fit. There is still room to layer with bulkier sweaters and close the front if necessary. The color is absolutely gorgeous in person, a rich jewel-tone!

The jeans are the Classic Straight Leg Jean, and unlike the other pair I tried on, they are a little more slim through the leg. They have the same 11 1/4″ high rise and 99% cotton 1% elastane construction but still felt stiffer than the previous pair. I sized down one to a 28 (as I typically do in Madewell denim), but these were too tight in the waist. I’d recommend staying with your true denim size (for me a 29/8).

I’ve been wearing these mules for years, but they’re a classic, so they had to make an appearance. They are consistently one of my most-worn shoes in fall. I recommend sizing up 1/2 size. They also come in black.

Shoulder Tee + Perfect Vintage Straight Leg Jeans

I bought this tee over the summer and fell in love. It has the accentuated shoulder look without any padding. It’s also thicker and more substantial than my other favorite Madewell tee (the Northside Vintage)! It fits TTS.

Let’s chat the jeans. They’re an update to one of my all-time favorite denim cuts: the Perfect Vintage Jean. Instead of having a more tapered cut like the original PVJ, these are more of a true straight leg with a relaxed fit through the thigh and calf. They still have a super-high 11 1/4″ rise with a ripped knee. I’m in the 28 regular length.

Chore Jacket + Perfect Vintage Straight Leg Jeans

This chore jacket is a more cropped, boxy version of shirt jacket. I sized down one, and it still has a relaxed fit. It’s also lighter than my classic Madewell utility jacket. So, if you’re looking for a lighter-weight, more modern version, this is it!

Let’s chat the jeans. They’re an update to one of my all-time favorite denim cuts: the Perfect Vintage Jean. Instead of having a more tapered cut like the original PVJ, these are more of a true straight leg with a relaxed fit through the thigh and calf. They still have a super-high 11 1/4″ rise with a ripped knee. I’m in the 28 regular length.

Drawstring Military Jacket + Perfect Vintage Straight Leg Jeans

I was excited to try this new military jacket style from Madewell, but honestly it’s not my favorite. It’s super wide and boxy fitting, even though I sized down one. I also pulled the drawstring to create more of a shape but it still felt too oversized. If the arms were more fitted, I think this would have been a win! I’d recommend sizing down two!

Let’s chat the jeans. They’re an update to one of my all-time favorite denim cuts: the Perfect Vintage Jean. Instead of having a more tapered cut like the original PVJ, these are more of a true straight leg with a relaxed fit through the thigh and calf. They still have a super-high 11 1/4″ rise with a ripped knee. I’m in the 28 regular length.

MWL Sweatshirt and Sweat Shorts

I have worn my Madewell tie dye sweat set constantly this spring and summer, so I was looking forward to trying a more fall-appropriate color. It totally lived up to the hype of my first set. It’s soft and comfortable, everything I’m looking for in terms of a matching set. Highly recommend! I’m in my true size in both.

More Madewell here! Or browse all of my recent try ons!