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The Fall Outfits I Love And Feel Really Good In (All From Madewell)

My life has become far more about utility than fashion, making me want to produce fewer fashion posts. I leave the house a few times a week but it’s not for fashion events. While I do miss dressing up and wearing oversized pink coats and snakeskin boots, it just doesn’t make as much sense for me in this “season of life”. So I’m far more interested in cute basics (that look like I still know what I’m doing and care) and ones that are comfortable but don’t scream “I’ve given up”. I had an Instagram partnership with Madewell so I went shopping and here is what I found that I actually need/love and will wear frequently. I found a lot that I love, but again am resisting the urge to hoard so know that these had to really grab me in order to add them to the closet.

Chambray Shirt | T-Shirt | Jeans | Sneakers

Do you guys remember these Cali jeans????? I bought them when Madewell first launched like 8 years ago and wore them til they fell apart (around year 4). When I put them on last week I was like “oh hey there old friend” and was reminded how good they are (they went away but somehow the little boot flare is back already!!). They are stretchy and therefore comfortable but without the feathering near the crotch (we really shouldn’t do that) that makes the stomach look like it’s protruding out. I find them very slimming (I wish I could have shown you all the jeans that I tried on that DIDN’T look good on me, but it’s not in my nature to go around bagging on myself or on other styles of jeans). So you’ll have to trust me that after trying on 12 pairs of jeans, these are the ones that were a solid “HELL YES” in both comfort, fit, and style. And I know that I’m not supposed to care about clothes that are “flattering” but I do, and these just are it you are into that. Right now I’m a solid 6, (I think) and first tried on the 28s (Madewell’s sizing is confusing), and they fit ok, but strangely the 26s were not tighter, just better scaled and more flattering. That’s all to say to size down a little bit in these (and they definitely stretch out).

Chambray Shirt | T-Shirt | Jean Shorts | Sneakers

Those sneakers are SO CUTE, and the T-shirt underneath says, “Let’s go Outside” and is a really good fit (flattering not too boxy, not too tight) I bought a small – which in Madewell world is a medium. The chambray shirt is boxy and these days I’m into wearing them unbuttoned and open. It’s a thing. OH and the shorts were so cute, with a little flare, and really cute in the butt (these more rigid than the Cali jeans so less good for sitting down all day if you know what I mean).

Blazer | T-Shirt | Jeans | Chelsea Boots

Same jeans, same shirt with an excellent tweed blazer with pretty details. It reminds me of a long tweed coat that I’ve been wearing since Charlie was born, but the shorter version. And these boots – oh these boots. I thought I had all the boots that I needed, but I didn’t have any (except clogs) that have a heel anymore. And y’all it’s been a while since I’ve worn heels and forgot what it does to your legs (and confidence). These are really comfortable and don’t feel like I’m wearing “heels” yet they give you the lift that is nice to have, visually. I’ve worn them so many times since I bought them (you can snag them on sale right now – they are typically over $200). I wear them with shorts and cute socks and they look utilitarian enough to even wear with stretch pants and an oversized sweatshirt without looking try hard. Big fan here.

Airpuff Long Shirt-Jacket | Jeans | Chelsea Boots

And then there’s this jacket that is so lightweight that it feels like you are wearing nothing, yet it’s so warm and cozy and looks cool. These are the same jeans that look great with the boots. This is a solid fall outfit that I can wear anywhere (soccer, a brewery, running errands). It was comfortable without being athleisure. Please note my trendy one-legged squat pose that my team laughed hard at me for EXECUTING LIKE A BOSS.

Blazer | T-Shirt | Cargo Pants | Chelsea Boots

Lastly, I tried on these cargo trousers that have this cute baggy almost balloon shape that I thought looked really cute with the more tailored tweed blazer. I cuffed them a bit and wore them with the same boots and felt pretty darn cute (TBH) which I really hadn’t felt in a while. Living on a construction site and working from home makes it so difficult to pull yourself together. Brian reminded me that I have a version of these pants already (some expensive brand I bought at a consignment shop years ago that I still love and wear) and he said (and I quote) “Do you really need two pairs of olive green drop crotch cargo pants?” and he was right. So I ended up returning them but if you don’t have even one pair of “olive green drop crotch cargo pants” then are you even living? Hot Tip! Men hate drop crotch pants! Hot Tip, Men! We don’t care! 🙂

Anyway, there are a lot of other cute things, including jeans that I really really really wanted, but didn’t let myself buy even with the discount because I don’t leave the house enough to warrant buying and hoarding the clothes (having less clothes is way more fun to manage both physically and mentally, TBH, not to mention better for the planet). But if you need new awesome basics, right now is a good time to buy what with the sale and all. I also bought these sunglasses, these socks, this cropped top tee, and my purse is still holding strong after 2 1/2 years if you need a good day purse (just grab yourself a cute strap to make it look cooler). That’s all. xx

**This post is NOT sponsored by Madewell – The Instagram stories were/are and we do affiliate links as you know, but we just love Madewell and I love recommending things that I love/use to others who might also love/use. xx


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21 thoughts on “The Fall Outfits I Love And Feel Really Good In (All From Madewell)

  1. Love the post and the conscientious way you choose and talk about your clothing, but what I perhaps loved most of all was the peek into your bedroom with furniture inside it and especially the peek AT THAT CHAISE!!!! Man, it looks so good their and I still really love the fabric you had it recovered in. I know things will probably move around a lot still, but the glimpse of it I got there just really got me super excited to see your new house with all your furniture in it!! (also as an aside: if you want to keep the fashion-saturdays but don’t want to recommend new clothes, I would also just love a ‘what I’m wearing this season’-segment or something like it just with things you already have (and you could then link the pieces that were available via affiliate links or whatever) no idea if that makes financial sense for you, but just to say you don’t have to present new stuff just for our amusement ;))

    1. Love the chaise, too! I spotted in Instagram stories, and it has me wanting a floral chaise in my bedroom.

      I love the Saturday outfit post idea. Linking similar items also works, but in general, I love seeing how people put the same items together over and over. I love how Emily shows a few pieces here in different combinations. Even if I don’t have the same items, it helps me think more creativity about what I have.

        1. Actually, I apologize for my comment. I realize that, by leaving it here, I contributed to the very thing that’s driving me a bit crazy in the comment section. Thank you for all you do, Emily and Team. I read the blog daily and never expect (or want!) you to be any less human than the rest of us. Much appreciation to you!

          1. I didn’t comment on the farm house (or mountain house) artificial grass post and can only speak for myself, but in this crazy political environment and as a long-time supporter of Emily it doesn’t feel right to be “gaslit” by deleting a post and pretending it didn’t happen. Of course, it’s Emily’s blog and she ultimately has the right to do whatever she wants.

          2. Yes I agree that the disappearance of the post is strange. The discussion and comments were very helpful and beautifully put ! I found it again on the Internet Archive (the comments are not yet lost), thank you

    1. It was deleted but can be found on the nonprofit Internet Archive. A similar thing happened in 2020 with the turf post from the Mountain House (only the comments were lost).

  2. Your sizing and fit review on the cali bootcut pants is SUUUUPER helpful – thanks for all that detail! You look adorable in everything, and I love these reviews

  3. Good to know the Cali jeans are back in style because I just wore my seven year old pair last night. They are still my favorite jeans! Also, I only buy clothes I find flattering. No need to feel bad about it.

  4. Where did you get that adorable phone cover? The black and white check…

  5. I love Madewell style but find them so frustrating. Their sizing is inconsistent, I have two pairs of the same jeans and the smaller size is actually the larger of the two. They don’t stock their stores well (at least near me) so it makes it impossible to try their things on in person. Then I’ve had several orders be cancelled or the wrong item show up. I keep telling myself I’m done with them but something always draws me back. I’m just weak. Sorry about the rant. You look great Emily.

    1. I like Madewell but their sizing is bonkers. I was just at a brick-and-mortar Madewell today and literally purchased one size L shirt and one size XS shirt. (I’m typically a S-M.) It’s wild, I can’t figure out their business model—maybe they make $$ on returns? Anyway, don’t buy online, go in store to try on.

  6. Great selection but geez we now have to apologize for wanting our clothes to be flattering. How absurd! What’s next, guilt for wearing makeup, dying our hair? There is no shame in wanting to look our best.

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