I just shared a Madewell try on in September, but y’all know my love runs deep. Plus, I was recently doing an inventory of my closet and realized that my fall tops were pretty much nonexistent. So, I took advantage of their current sale and ordered a few new items to share with y’all for a little October Madewell try on! And you can actually thank my mom for a few new jeans finds too! ?She placed an order for four different styles and let me “borrow” them to share with y’all! Team work, y’all. Team work.

October Madewell try on

As far as sizing goes, I’m 5’7 1/2″ with a short torso and very long legs! I typically wear a 28/29 in jeans or a size 8. (For Madewell, I tend towards a 28!) 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 my size and 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!

Pleated Sleeve Top + Slim Wide Leg Cropped Jeans 

This outfit may look oddly familiar. I first put it together in my September Madewell try on! But then I used it this week when creating a style session for y’all! Clearly it’s a combination that I love! 

If you’re looking for lighter-weight tops for heading into fall, check out this one! Firstly, the color is beautiful! (It does also come in other options though!) It has a wider rib to it, a relaxed fit, and a pleated, slightly ballooned sleeve. It’s also bracelet length, which I always find so feminine. 

And onto the jeans! I have been wearing these non-stop lately! They are so flattering and I like having an alternative to skinny or straight leg jeans. The slimmer wide leg is very flattering on. Sizing-wise I struggled a bit! I ended up with the size 30 (a size up from my typical 29). But now that I’ve worn them a few times I wish I had stayed with the 29! They do loosen up with some wear! Stay TTS! 

Top (medium – TTS) | Jeans (30 – TTS) | Flats (TTS) 

Acorn Peplum Top + Denim Skirt 

Ok, how precious is this top?! It has a fall floral print with tiny acorns at the chest!! It’s a very lightweight corduroy and so flattering on as well. The waistline is peplum and the sleeves have small ruffles on them! I tried on a small but would prefer a medium for more of a relaxed fit. 

I’ve been looking for a darker wash denim skirt of fall, and I ended up taking this one home. It has plenty of stretch to it and is very flattering on. I also love the mini front pockets! Since it’s been so stinkin’ hot here lately, having items like this make dressing for fall more bearable! I sized down one to the 6 and like the fit.  

Top (small – TTS) | Skirt (6 – size down one) | Mules (size up 1/2) | Headband 

Blazer + Tank Bodysuit + Slim Wide Leg Cropped Jeans + Leopard Booties 

I talked at length about this blazer on stories last week and convinced myself that it was a wardrobe necessity. ?It has an oversized boyfriend fit and is double-breasted. I love the black, gray, and white plaid as well. It’s very versatile! The length is also perfect. It covers the booty, meaning you could wear it with leggings if you wanted to dress it down! It would obviously also work so well as an office-wear piece! I ended up exchanging for a small and prefer the fit!

Beneath the jacket I’m wearing a tank bodysuit! I’d been wanting on for layering and it fits wonderfully. It is ribbed and the straps are wide enough to wear with a regular bra. While I know cooler weather is eventually coming, I went with a tank version since it’s nursing-friendly! It has a thong bottom and two rows of snaps, which I appreciate as someone with a short torso! It’ll be perfect for under all types of jackets and cardigans. It fits TTS. I’m in a medium. It also comes in gray!

Aaaand the booties. I finally gave in. I felt like leopard booties were impractical, but in a one week timespan, I’ve already worn them twice. So, I guess any worry about versatility went right out the window! ?They have a nice thick block heel and fit TTS.

Blazer (medium – size down) | Bodysuit (medium) | Jeans (30 – stay TTS) | Booties (TTS) 

Blazer + Tank Bodysuit + Tencel Skinny Jeans + Leopard Booties 

This is a screengrab of a video I took hence the quality and mid-talking face. But I wanted to share how the blazer looks with skinny jeans as well. These are my most-worn skinny jeans that I purchased from Madewell last year. They’re a tencel denim, meaning the fabric is thinner and super-soft. They still have stretch to them as well. I’m in my typical Madewell size 28. 

Blazer (medium – size down) | Bodysuit (medium) |  Jeans (28 – size down 1) | Booties (TTS) 

And onto the jeans from my mom’s order! THANKS, MOM! ?

Skinny Jeans 

I don’t know how I hadn’t tried these before. They are a bestseller on Madewell’s website with rave reviews! One reviewer mentioned that they made her bootie look like Cindy Crawford’s in the 90’s. And y’all, I am here for that. ?They are just as wonderful as all the hype! I love the classic dark wash. They’re going to be super-versatile year round! The rise is a 10″, hitting right at my belly button. Also, I feel like they really hold me in. These are probably one of the most flattering pairs of jeans I’ve tried on in a while. Needless to say, I ordered a pair for myself. I’m in a 28.

Top (medium – TTS) | Jeans (28 – size down 1) | Mules (size up 1/2) 

Vintage Jeans 

I have a pair of really light wash vintage jeans that I bought at the beginning of the year. These are just as good. They actually remind me a lot of my favorite boyjeans that y’all always ask about. If you loved those, you’ll love these! The denim is super-comfortable and has some stretch. I would prefer a tall for extra length! I’m in the 28.

Top (medium – TTS) ) |  Jeans (28 – size down 1) | Mules (size up 1/2) 

Black Tencel Skinny Jeans 

Another really great pair of jeans, y’all! These are the same tencel fabric as my dark wash skinnies I shared with the blazer above. The fabric is some of the softest I’ve ever tried in jeans. These are more of a mid-rise at 9″ and hit below my belly button. For some reason, Madewell’s black washes tend to have less stretch. In these I’m wearing a 29. I’d recommend staying with your true size. 

  Top (medium – TTS) | Jeans (29 – TTS) | Mules (size up 1/2) 

Slim Boyjean 

I don’t know if I’ve ever looked more ridiculous in a pair of jeans. I don’t know what it is about the boyjeans, but I’ve learned by now that I have to order them in talls! The skinny jeans I stick with regular length, but these are more cropped. (I just purchased these boyjeans in tall length from last month’s Madewell try on and kept them!) I’m in a 28, and they do fit great at the waist. 

Top (medium – TTS) | Jeans (28 – size down 1) Also go with the tall 5’9″+!! | Mules (size up 1/2) 

Clipdot Ruffle Top + High Rise Skinny Jeans

This top is the most beautiful deep jewel-toned green! It has a high neck with elastic and a ruffle. The sleeves also have ruffles, but because the shoulder is dropped, they don’t add any puff to the shoulder. It is slightly boxy in fit, but looks great tucked. If you need a work to weekend top, this is such a great option! I’m in a medium and like the fit. It’s under $50 and comes in two other colors, including pink and burgundy.

These are the same jeans I shared earlier– you know the Cindy Crawford bootie jeans?! ?I am so glad my mom ordered them because I probably wouldn’t have found them otherwise! They are so flattering on and I love the high 10″ rise. I ended up ordering the 27 and the 28 for myself and I’m in the 27 here. I’m going to be keeping the 27. They’re just slightly snug but I know they’ll break in a bit like my other Madewell jeans.

Top (medium – TTS) | Jeans (27 – size down) | Flats (TTS) 

Long Sleeve Eyelet Top + High Rise Skinny Jeans

This top has a similar neckline to the last one! It’s higher and has a ruffle on the collar. The neckline and arms are eyelet, which I love! The back also has a bow, so now you know I’m completely sold. ?I wish it came in more color options, but who am I kidding? I probably would have ended up with the black anyways. The body fits straighter in this top than most at Madewell, but I’d still recommend sticking with your true size. If you prefer a blousier look, you could size up one.

Top (medium – TTS) | Jeans (27 – size down) | Flats (TTS) 

Peasant Top + High Rise Skinny Jeans

One of my favs from my order! The background is a beautiful peachy-orange! And the floral print looks very fall with purple, red, and touches of olive green. This is another one that could be dressed up for the office or worn on the weekends. It has a tie at the neck, but I prefer it undone! There are also small ruffles at the sleeves. Fit is oversized but I like the medium on me. 

Top (medium – TTS) | Jeans (27 – size down) | Flats (TTS) 

Swiss Dot Top + High Rise Skinny Jeans

I’m getting retro vibes with this top! It is button-front but has a side zipper to get on and off. There are also bows at the sleeves with tiny keyholes. It is more fitted and gathers a bit at the bust. There is also some gathering at the waistline in the back. It looks cute both tucked and untucked! I’m in an 8 and like the fit. I’m surprised at how flattering it is on!

Top (8 – TTS) | Jeans (27 – size down) | Flats (TTS) 

Long Sleeve Baby Tee + High Rise Skinny Jeans

Such a cute 90’s-inspired tee! It has a wider scoop neck with a scallop detail at the neckline. It’s a true fitted tee that comes in five colors, including gold, black, white, and more! If you want a bodysuit alternative, this is it! Just tuck into jeans, skirts or high waisted pants.

Tee (medium) | Jeans (27 – size down) | Flats (TTS) 

Blazer + Long Sleeve Baby Tee + High Rise Skinny Jeans

Just another quick peek at this blazer but in the smaller size. I sized down from the medium to the small and prefer the fit. It’s still able to be buttoned but is less wide, which I find more flattering on me. Sizing is limited at Madewell, but it’s also available at Nordstrom here!

Blazer (small – size down) | Tee (medium) | Jeans (27 – size down) | Flats (TTS) 

Bobble Sweater +  High Rise Skinny Jeans

Another look at this sweater I purchased from the Shopbop sale last week. I love the texture, the peachy color (I’m wearing “Avalon Pink”), and the bobble sleeves! It fits a little wide and boxy, so I suggest sizing down one. I’m in the small. 

Sweater (small – size down) | Jeans (27 – size down) | Flats (TTS) 

Denim Babydoll Dress 

An on-trend version of a classic shirt dress! This one has buttons that come down to about an inch above my belly button. It’s 100% cotton denim with a babydoll cut! The color is more of a slightly faded washed black. The sleeves are slightly puffy and ballooned! They hit at a bracelet rather than full length. I sized down to the small after seeing it on the model, but I don’t think I necessarily had to. If you have a larger bust, I would not recommend sizing down as there is no stretch. 

Dress (small – TTS) | Flats (TTS) 

See more Madewell favorites here!