Style

What Are Your Fall Essentials?

fall brooklyn street

Every fall, I settle into a uniform and wear two things over and over: this sweater and wedgie jeans. What do you wear on rotation? As the weather grows cooler, here are a few cozy essentials for work and weekends…

What are you wearing these days? I also love these everyday heels — and how cozy is this?!

P.S. The joy of a work uniform, and the clothing trend we’re seeing everywhere.

(Top photo by Stella Blackmon.)

  1. Kelly says...

    Great round up! I have been scouring the internet for a Jeans roundup (particularly the most flattering styles by body type) and haven’t found one yet. Would love to see CoJ’s take :)

  2. Bea6 says...

    Would love feedback about the Blundstones! Lightweight? Comfy? Made for indoor/outdoor use? Last a lifetime kind of boot? I’m not familiar with them. Thank you!

    • Nicole says...

      Hi! I’ve had my Blundstones for a little under a year now and I absolutely looooove them. They are very comfortable and have never troubled my feet. I have them in black so they really match well with everything – I even wear them to work on Fridays! Love that they are waterproof. Makes the iffy weather much more manageable! I definitely think they are a lifetime boot. I wear them out to brunch/work, or on a walk in the woods. Easy to wipe clean, too. I cannot express how much I love them!

    • Em says...

      I 100% agree with Nicole! Definitely a lifetime boot and they are so versatile! I absolutely love mine.

  3. Sarah says...

    Every fall, I break out the Forever 21 men’s scarf I bought yearssssss ago on clearance for something like $2.90. It’s thick without being cumbersome, ridiculously soft, black and white checkered so it goes with most everything.

    And of course, sweaters. I’m hanging onto some old Merona sweaters from Target that are a couple years old – a mustard yellow, a grey with a bee on its front.

    • Em says...

      Isn’t it the best when an item from Forever 21 actually lasts?!

  4. Lindsay says...

    I just bought that cashmere sweater yesterday! In burgundy. It’s so soft and flattering. I think I’ll get black too……do wedgie jeans require a tiny waist???? I do Like the madewell curvy skinnies.
    I also just wear jeans and sweaters (love Nordic fair isle) plus cute coat and either sneakers or boots.
    But I’d like to branch out this year….I’m thinking of getting a few non denim pants and some silky blouses.

  5. Michelle says...

    Mixing the desire for sustainable fashion and fall, I will add an item on my wish list: flannel shirt from American Giant. They have worked to restore US based textiles, bringing back the classic plaid flannel ins all batches earlier this year. Weather was warming and the price isn’t cheap (Asia has spoiled us) so I didn’t get one before they sold out. But I’m following them and have vowed to get one when available. May also make the men’s an Xmas present for my husband. Less specifically, fall is white jeans and summer footwear until the day temp is in the low 50s. The it’s bootie and sweater weather and a palette that shifts darker as the days get shorter. But fall in MN is all about Indian summer vibe, even if the weather isn’t delivering.

  6. Kaitlin says...

    That mock neck sweater dress looks like one I wore everyday during my pregnancy.

    I can’t wait to break out my denim jacket and find a new pair of corduroys. But I’m most excited about something I’ll only wear inside the house: I splurged on a pair of handmade felted wool slippers from Nepal that fit beautifully and will help me take care of my feet over the colder months. They’re basically like Blundstones – but slippers!

    • Sue says...

      I just bought my first pair (only?) of Blundstones! These were my fall splurge. Now I’m looking for a non fast fashion cord mini to pair them with.

  7. Jen says...

    What a timely post! Here in West Virginia, today was our first brisk day. Usually my outfit is skinny jeans, black riding boots, a black and white geometric patterned top, my floral mauve silk scarf, and a black beanie I crocheted.

    Also, here’s a suggested post idea: how to get started in thrift/consignment shopping. I am just learning the ropes myself and am flabbergasted it took me this long! It’s a great way to build a new seasonal wardrobe especially if you like designer pieces.

    • Susan Magnolia says...

      I love to hear that others also visit resale and thrift shops. Most everything I wear is pre-worn and I love it. I use the local consignment shop when I need a piece that is nicer or time sensitive, like shoes and boots or a dress for a wedding. I love to clothes but cannot afford the price or the thought that fashion is quite wasteful.

  8. Lisa says...

    There was a super cold winter (by London standards …) two years ago and I got a big, Ivory wool jumper. It was amazing (until I shrunk it in the wash). I wore it with skirts, jeans, standing in parks waiting for kids. Last winter it was the merino polo necks from uniqlo – great for layering, easy to wash and just lovely. Another great buy was suede booties from Bobbies. I managed to get them in the sale – they go with everything and are so comfortable

  9. Vishakha Gupta says...

    Mine is a dark sultry perfume like Jo Malone’s Velvet Rose, or for a cheaper option Sonia Kaushik Pink Innocencia, a berry lip, a couple of great cashmere or merino wool sweaters, leather jacket and faux sude tights with booties. Also I’ll second the warm fall beverages, cider is my drink of choice.

  10. Diana says...

    they look adorbs but why sell jeans by calling them “wedgie jeans” – that’s like a sweater called “itchy sweater” or shoes called “toe pinchers.”

  11. Jean Livingston says...

    I’ve found some simple, inexpensive ones at Nordstrom Rack!

  12. Rin says...

    Cord miniskirts! I now own four – dark purple, grass green, magenta and navy with red embroidered hearts. Am eying up a grey one, too. Add a cardigan, tshirt and tights and you have an outrageously comfy outfit that is just smart enough for work. I may never wear jeans again!

  13. Makenzie says...

    As a Houstonian, I suppose I will put away my summer bikini and pull out my fall one piece swim suit.

    • Kimmie says...

      Ha! Sounds completely cozy.

    • Anna says...

      Austinite here and I concur. I’m dreaming of the sweaters I can pull out in ……January?

    • JB says...

      If it makes you feel better, we have the same problem in LA :(

  14. These are all such beautiful pieces! My most worn pieces definitely include black leggings, oversized hoodies, and a whole lot of coats when I’m heading out. One thing I really want to buy this year is a leather jacket (probably thrifted!) So there is that to consider too. Boots are also a definite beloved item for the chilly season.

  15. june2 says...

    For me it’s about the baselayer: merino leggings and crew under everything at all times. But the uniform tends to be wool or fine wale corduroy pants in a skinnier leg and some type of cashmere or other soft knit top. I like them to be more decorative than a crew. Also a good soft wrap, either just dangling on either side or else wrapped around my neck. I have many to match anything but softness is key. It keeps my neck warm without the constricting feel of a turtleneck, a garment I’ve never been able to adapt to. Also good warm indoor booties are a must – no street shoes indoors.

  16. Susie Nemeth-Wild says...

    I decided to make a list of my fall essentials before scrolling down to see yours. My list: a cozy sweater, mug of tea, apple cider, pumpkin walnut bread, cozy blanket, candles, a good book, and many apple desserts.

    • Joanna Goddard says...

      LOVE yours!!!!

    • Sasha L says...

      This is a really good list Susie!!

      I’m adding a sweet dog, with his head on lap.

  17. Rezia says...

    For me, fall means a knee length dress, leather jacket (or blazer/cardigan for the office), black tights and a scarf.
    Adding tights helps me keep wearing many of the dresses that I wore through the summer.

  18. Tracee says...

    Does your sweater pill up and need “shaved” often? I’ve almost given up on the wool altogether because the upkeep is so frustrating.

    • Joanna Goddard says...

      are you asking about the jcrew cashmere sweater? if so, it hasn’t pilled for me. it’s held up so well with SO many wears over the past few years. xo

    • Jill says...

      Joanna, how do you wash it, and how often? I crave cashmere but am confounded by this question, even after intense googling!

    • Joanna Goddard says...

      i actually wash it by hand mostly and then every now and again take it to a green dry cleaner. hope that helps! xo

    • Jill says...

      Very much, thank you!

  19. The mercury is beginning its steady decline where I live in the heart of the Canadian Prairies. No complaints; I live for little shoe and sweater weather. I recently saved up and purchased a glorious wool No. 19 jumper from Babaa in ochre. It is the ultimate camping/ walking/ hiking/ errand running warming piece. I always feel chic when I wear it; especially when paired with good old high waisted black jeans or my old mended Levi’s, a light cotton button up, a fantastic wool chapeau, Sunday Feel celestial studs and quality leather lace up boots or kid leather glove shoes. Ready for anything. There is something so sacred about summer’s wind down. I like to ease into the cooler season by listening to Neil Young’s Harvest Moon album on vinyl, burning beeswax candles, running hot baths, making warming food and drinking red wine. Heaps of red, red wine! Happy Autumn, all!

  20. Suzanne says...

    Why oh why is it so hard to find a simple cardigan?! I swear I look for these every year and am without much luck…

    The other thing I’m really into lately is well-made plaid shirts that aren’t think flannel.

    These are my fall staples with skinny jeans and either boots or booties.

    • Sarah says...

      Suzanne, depending on the weight of cardigan you are looking for, Uniqlo has classic options in great colors and materials. It’s worth a look!

  21. Carrie Jones says...

    CANDLES, striped long sleeve shirts, my Birkenstock Bostons and right now I’m in search of the perfect boot cut cords. Fall stars September 1st for me, and I am in my full glory right now. Best time of the whole year.

  22. Maire says...

    I am really into the look of scrunched socks visible on top of my suede Jeffrey Campbell short shaft Western boots + tights + flowy babydoll dress + oversized cardigan. I love how much you can play with layers in fall and winter, it feels like such a more creative time sartorially.

  23. Jessica says...

    ugh it’s still 94 in Atlanta and it’s killing the Minnesotan in me. I’m sweating in my sweaters which is the lamest and least comfortable form of protest.

    • jenn says...

      Its 85 in Iowa…fall is not really here yet, kids.

  24. Diane says...

    I was pregnant last winter so am excited to rediscover my wardrobe this year. We’re in Tel Aviv so it’s still 30 degrees every day, so our winter clothing wearing doesn’t really start until early November and ends about early March. I love high waisted straight leg jeans, tucked in tops, comfy jumpers, brogues and Chelsea boots. My mum just passed on her Banana Republic trench coat so I’m also excited to wear that this year.

  25. Last year I discovered an old pair of leather booties with a block heel as I was going through my Nana’s closet. They became a staple, along with the mocknecks and turtlenecks that are always my go-to in fall and winter! I have enough (almost all from Goodwill or my mother’s closet) I could probably go two weeks without wearing anything else. Last week there was a day where it was a cool 75º (I live in Atlanta) and, perhaps against my better judgment, I committed to wearing a new sweater, though not a turtleneck, all. day. long. No regrets:) Fall cannot come soon enough, but in Georgia that’ll probably be mid-October!

  26. Abbey Richards says...

    I’ve realized of late that my “Earth Shoes” booties are my non-summer staple. The moment there was even a hint of cooler weather (and sometimes when there wasn’t) I broke them back out. It may be because they happen to be the most comfortable and versatile shoes I have at the moment, but I love them.

  27. Kathy says...

    Joanna, I’ve always loved that JCrew sweater when you link to it…until I remember it’s hand wash only. Do you hand wash it? I feel like sweaters always get ruined when I hand wash.

    • AJ says...

      I have many JCrew cashmere sweaters. I buy soap specifically made for cashmere and wool (by the brand “The Laundress”). I have a wool setting or hand wash setting on my washing machine that I use with cold water. Lay flat to dry and they are perfect. I wash my husband’s cashmere and wool the same way. I wouldn’t hesitate to actually hand wash if I didn’t have my machine setting. They wash perfectly every time!

  28. Mel says...

    I know this is going to sound ridiculous to compare but I just got done telling my husband how crazy different fall in WI and MN are. I’m from southern WI where it’s still in the 80’s and will be for a bit but in MN we’re already consistently in the lower 70’s and 60’s. In WI it felt like we had one month of fall (October) and then wham winter. But here it feels like a solid 2 months of it and I LOVE it. I’ve already unpacked my thin sweaters which I love to wear with shorts and tiny tennies. I’m also a fan of light dresses with sweaters popped over. It’s the perfect temperature to be half summer half fall.

    • celeste says...

      Moving from central WI as a kid to southern WI I love the extra sunlight! My in laws live in northern WI and talk about us moving there and I think, “the lack of winter light would do me in!”

  29. K says...

    Living in LA where its still going to be in the 90s for two more months, pining after the pretty and cozy Fall cardigans and jackets I see in stores/online. One day…
    I usually wear jeans with a floral or striped shirt, or a cozy cardigan/sweater/denim jacket with a solid top, and Vans/Converse/other sneakers (stay at home mom here so have to be able to run with the kiddo), and then accessorize with tiny stud earrings or hoops. Obsessed with light jackets – love that they are so forgiving and easy to fit. Madewell has cute (although pricey) slingback flats I’ve been eyeing…so pretty.

  30. Your work is so full of useful information.

  31. Megan Snyder says...

    Why do we wear the same things all fall and winter? I have no shortage of sweaters and leggings yet I wear the same soft, worn-in black sweater (with a giant hole in the arm pit that I precariously hold together with a safety pin) and faded black leggings. WHY?

  32. MJ says...

    I don’t like dressing for fall or winter. I have yet to find the balance of cute, comfy and warm. I work from home and so by January I’m in workout clothes like leggings and sweatshirts. This might be my year to try a more pant-like legging and tunic/sweaters. Any suggestions on where to shop?

    • Emily R says...

      Me either! Anything that is warm looks terrible on me, and when I look nice, I’m frozen. Give me summer all year long!

  33. Jessica Camerata says...

    All about the new Madewell pieces that you shared. I think I’m on the hunt for good dresses for fall. I tend to only wear them in the spring and summer and totally forget about them once it cools down. It then becomes jeans and leather jackets non stop.

    xo Jessica
    My Style Vita

  34. Andrea says...

    Our winters are all over the place where I live but my go to fall/winter look are cardigans of different weights with skinny jeans. I wear a tank top underneath and as crazy as this sounds I actually wear them backwards to have it a tad higher on the neckline and with a cardigan it’s perfect. I’m not a print wearing gal but sometimes I’ll find print tanks and it adds a pop! And yay for others who hit up the men’s section on cardigans!!!!! I have found great ones and you see some really unique colors!

  35. Carter says...

    Slim fit/skinny fit jeans, big chunky sweaters and my favorite pair of shoes that are so comfy but look so cute…Dansko Maria booties. The sole looks like a natural wood but is really the comfortable dansko style sole. They are heaven to wear and so very cute!

  36. Love these picks. I literally just wrote out my fall list on a post-it note yesterday! New black jeans, new regular jeans (trying Everlane for the first time!), a comfy cardigan, actually find bras that are comfortable, ALL new undies, two new dresses and a pair of black loafers. I’ve realised I’ve kept clothing for 5+ years that I love but just don’t wear anymore, so want to donate all of it and make space for this that I love now, not just keep for nostalgic reasons.

    • Julie says...

      Everlane jeans rock!! I have both stretch and non-stretch pairs and they’ve all held up beautifully.

  37. Katrina says...

    Sweaters! Scarves! As a knitter this is my favorite! I get to show off my favorites that I made!
    High waisted dark wash skinny jeans, sweater (or flannel, I love flannel), long sleeve tshirts, denim jacket, booties or oxfords and I’m in heaven! Lovely walks with warm drinks and no boob sweat!
    Can you tell I really love autumn?

  38. Poppy says...

    AHHH wedgie jeans are the bomb! i have dark ones, i like that distressed finish but i will try to get there naturally. it’s been too hot to wear them, time to dig them out and start making outfits–i.e., those jeans, a certain weight of t-shirt, belt with Cocky buckle (from Bones!! my bf got it for me one xmas, my fave present ever) and i just got a pair of white converse high tops. yep, that’ll do. still don’t trust myself in sweaters, menopause

    • Poppy says...

      omg i forgot about my boots, i have black patent fatboys that i wear with everything. man i’ve had those boots for twelve years and still get compliments almost every time i wear them

    • Lori Benjamin Brenig says...

      What are Fatboys? Are they sneakers?

  39. Lorraine says...

    let’s face it, as much as i try to opt for prints and brights – nothing says fall to me like a black coat, black tights, and black boots. throw in a black turtleneck and some dark wispy skirt. a scarf, maybe there’s your pop of color. this is how i dressed in high school, so 25 years later this somehow still rings true for me.

  40. Sarah Clews says...

    I’m done having babies so this is my first fall getting serious about what my fall/winter wardrobe should be like. I get super cold in the winter so I know that I need serious sweaters/pullovers and no cute but impractical thin blouses for everyday. I’m learning! And last year I bought myself a pair of serious winter boots.

  41. Joaquina says...

    What a lovely topic, we in Southern CA are roasting. Thinking of fall temps is a nice reprieve. CA fall essentials:
    Turtlenecks
    Oversized v-neck sweater
    Straight-leg denim
    Lightweight trench
    (Vegan) Doc Martens
    Vans high tops

    • liz says...

      Hi X! Thankfully, in 2019 not all ethical/sustainable brands are that priced that crazy. And yes, I am pay check to pay check and still refuse to support brands that very recklessly and knowingly destroy the planet and harm its workers. It just means I buy much less than I used to, mend what I have, and buy second-hand clothing more than not. Otherwise, we’re just going to stay in this huge-corporation status quo that is literally killing people and the planet, which then will result in more death. Not sure how you can justify otherwise, honestly.

  42. Darrah Blanton says...

    Hi cup of jo, I commented earlier this summer about fast fashion brands like H&M, and how the Netflix documentary “the true cost” has shown how damaging these brands are to the environment and also exposed the low wages and unsafe conditions of the laborers that make these clothes. I am very disappointed to see that you are still linking to these brands– in this post, the very first link. I don’t know if they are sponsoring you, but if you watch this film I am confident that you would not want to be associated with them. Please consider.

    • K says...

      Absolutely this is something people should consider, but we should also note that buying expensive investment pieces that promote sustainability is not possible for everyone. Many people treat h&m as investment pieces, not fast fashion, because they take good care of the product and get a good life out of it. A blanket dismissal of inexpensive brands and clothing isn’t reasonable!

    • Hilary says...

      You’ve brought up a great point, but I agree with K that sustainable (and expensive) fashion is not attainable for everyone. I read an interesting article recently about how being environmentally conscious is really a privilege of the upper and middle classes; many are not able to buy local/organic, for example. I, too, try to buy more sustainable pieces. On the other hand, I have dresses from Old Navy that I’ve had for 10 years and have repaired, so I don’t have to buy new clothes to replace them. It’s great to bring attention to how we can be doing better, but also not shame people who have to help the Earth in other ways! I’d hate for people to think it’s an all or nothing mentality when combating climate change/labor concerns/etc. The documentary sounds super interesting, so I’ll be sure to check that out to try and make more informed purchasing decisions.

    • Liz says...

      Whether or not you treat h&m as an investment piece doesnt cancel the destruction they are doing to the environment with their manufacturing and sales methods, not to mention the ways workers are abused. The only way to get companies like this to stop is to stop giving them your money.

    • Kristen says...

      Yes, I wish everyone would watch The True Cost just once in order to re-think the rate of clothing consumption in this country. I realize that sustainable brands are not financially feasible for everyone, but seeing this documentary would make any viewer pause and re-think buying things they might not really need — especially from fast fashion brands. Everyone is now aware of the plastic problem facing our planet; not as many know/think about the fact that the clothing industry is one of the top polluters on the planet.

    • Sarz says...

      Darrah, I saw that doc too – I feel you!! However, like K, I find it sadly unreasonable to think that *everyone* will swear off inexpensive clothing retailers. I’m fortunate to have a wardrobe of quality pieces, but that’s only because I’ve invested hundreds of hours hunting through the thrift shops that are plentiful in my big city. Many people lack either the time or locations to find second-hand items, or, like me, they just can’t afford those new, ethical brands. Let’s not stop spreading the word, though! Every small gesture adds up!! 😊

    • Sarah says...

      Hi everyone! I think we can move beyond expensive clothing options that are also sustainable. It’s true that even if you wear H&M, Old Navy etc. for a long time, their processes are extremely harmful to local environments, let alone the atrocious employment standards. Having just spent three months in Bangladesh, where the majority of H&M garments are made, women make a minimum wage of 8,000 Bangladeshi take per month (around 96 USD per month). As a result of this wage, they largely live in informal settlements (i.e. slums) where they experience 1) unequal environmental conditions (exposure to flooding, for one, and extreme vulnerability to earthquakes and fires) , 2) limited water and electricity (note that this is highly uneven dependent on living environment) and, 3) highly gendered conditions resulting in harassment and lack of societal respect. All in the context of no healthcare and no maternal leave! Even so, garment workers in Bangladesh don’t make enough money in these positions to avoid relying on credit to meet their day-to-day needs (data by a great source Microfinance Opportunities has found that the women use this credit primarily to buy food – https://www.microfinanceopportunities.org). I hope this sheds some light on why prioritizing the individuals making clothing for H&M is so, so important. But, circling back to cost consciousness, what is one to do? First, putting pressure on transnational brands such as H&M is necessary. Corporate actors respond to their customer bases! Second, buying second-hand to reduce consumption is key. Great quality cashmere has been around for a long time. Finally, to the Cup of Jo team – while consumption is clearly a core part of your business and I have enjoyed your blog since the beginning, clothing recommendations included, I urge you to take seriously the need for consistent sustainable purchasing recommendations. You are a POWERFUL entity and have the ability to shift narratives and behaviours. I would be happy to speak to this more if anyone is interested :).

    • X. says...

      I often wonder if people who make these comments about buying exorbitantly priced “sustainable fashion” and “statement pieces” have any clue at all about how hard a family can struggle just to put food on the table and get the electric bill paid? If the choice comes down to buying their kid badly needed new shoes at one of these businesses you condemn, or buying groceries, would you seriously judge them and shame them for not keeping sustainability at the top of their priority list? Many people are doing their best just to take care of their families and make ends meet. Why put the weight of the world’s problems on the shoulders of people who may be the least able to take the action you are directing them to take? It might have more impact to focus your activism instead in the direction of policy makers and industry leaders.

  43. Wmom says...

    A swim suit, shorts and dresses. I work in a school and live in Hawaii.
    :)

  44. Danielle says...

    How timely! I’m a southerner preparing for my second Midwestern fall/winter. My colleagues have complimented my summer wardrobe frequently enough recently that I’m beginning to realize I still don’t actually know how to dress for actual cold seasons? And/or my winter wardrobe really is as sad as it feels.

    I’ve got a pair of high-wasted trousers in a deep burgundy on my to-sew list, but I realized today that I have no idea what else I want to wear once the weather starts to cool off.

    • Mel says...

      Layer my friend! I’m in Minneapolis and a midwesterner for life (I did live in the south for a year and was lost on how to dress for so much warm weather, I own i’m not joking 40+ sweaters) as a person who is *blessed* enough to live somewhere that got down to -50 last year I can say i’m a professional at layering. I used to work in a business professional office and my go to was an undershirt, a silk blouse a chunky sweater and either skinny cigarette pants with loafers or big trousers with booties. Though I would never, ever wear either of those shoes outdoors – always packed, or kept at the office and wear those ugly winter boots outside. Not worth ruining your pretties.

    • Sam says...

      If you wear a lot of dresses and skirts, I definitely recommend fleece-lined leggings for cold seasons! You get to keep wearing some spring/summer favorites while feeling like you’ve got pajamas on, it’s my favorite.

    • C. says...

      I grew up in the north and now live in the south, and my suggestion is to pay attention to fabric (wool, fleece, etc) and opt for things that are really designed for cool weather, as opposed to fashion. My southern friends often prioritize style, and they look good! but end up chilly.

  45. Lauren says...

    I’ve found my summer capsule at least for work with black pants and a linen shirt but I’m not sure how to adjust for fall this year. I think I may just wear the same thing+ Chelsea boots and a cardigan but I’ve struggled to find a cardigan I really like. I’m trying to buy second hand or ethically made and that complicates it + I just cannot handle anything that must be dry cleaned!! Maybe a blazer instead? Other ideas??

    • Amanda says...

      Jcrews Sophie sweater blazer is my go-to for something in between a cardigan and a sweater, and it layers on top of shirts if you roll the sleeves up. You can sometimes find it on Poshmark. I also look fir the chunky cardigans from everlane on Poshmark.

  46. jet says...

    Since I live in Southern AZ I wear the same things as in the summer with darker fall-ish t shirts.

    • Leah says...

      I was about to comment that in AZ the weather isn’t really cooling down.
      How I miss fall and fall wardrobe…

  47. Ann says...

    Fall means soft black turtlenecks, jeans, and black boots for me!

    Also love the photo on this post – one of the prettiest blocks ever :) I live in Bk Heights, and my sister and I may have actually seen you this weekend on Clinton riding a bike? We were the twins who grabbed hands and squeaked when we saw you, haha :) both big fans!!

    • Joanna Goddard says...

      Haha you are so sweet! I think I was on a bike ride with Anton! He was on the sidewalk and I was on the street path:)

  48. Lou says...

    Come on up to WI! We have real fall and realer winter.

  49. Kerry says...

    I have a couple COS shirts and sweaters on heavy rotation along with black skinny jeans. You can dress it up, dress it down. I may transition to wide leg pants or jeans as my go to this Fall. And of course a chelsea boot.

    • Ei says...

      Thanks for being more size inclusive in this post.
      As a teacher, my fall struggle is wearing “real” shoes every day.

  50. Kristin says...

    I pretty much only wear dresses in the summer so I’ve really been looking forward to denim (the perfect vintage 501s), trench coats (all coats!), boots, and all the shirts in my closet I haven’t worn in three months. Gucci loafers too – so nice to wear those yesterday.

  51. Amy says...

    I think I got stuck in 2015. I’m not sure I’ll be rocking any of this! Oh well, most of us end up stuck in a particular decade eventually ;)

  52. Cait says...

    When COJ links to a dress you’ve been stalking for awhile and you hope it doesn’t sell out before you can afford to buy it, haha…

  53. Nally says...

    The slim, down vest (uniqlo), layers, layers and finally scarves, yes!

  54. Cynthia says...

    I love my sweaters and boots.

  55. Last year I bought my first pair of Blundstone boots and I am obsessed! They make me feel like I could do anything! Traipse in some leaves holding a PSL or survive the zombie apocalypse!

    • Avalanche Lake says...

      Me too! I got the all weather insulated ones and love how I could wear them through the whole winter and not worry about rain or snow or slush or icy streets! Now I’m thinking about a “fancier” pair–could I get away with wearing them at the office??

    • elinor says...

      I LOVE Blundstones! I got mine last December, and have worn them constantly since. They really hold up well!

    • Laura says...

      All these posts on Blundstone boots makes me want to try them! Where do you buy from?

    • Lisa says...

      Yes! Blundstones have been my favorite pair of shoes since I got them last winter. I have worn them consistently all winter and spring and cannot wait to wear them daily very soon:)

  56. Mouse says...

    Uniqlo heattech leggings! And Eileen Fisher sweaters, Blundstones, and down vests.

  57. Colleen S says...

    My uniform is skinny jeans, Chelsea boots from Target that I bought two years ago, and an array of tops. I live for fall, even though the part of Northern California I live in doesn’t get cooler weather until the week of Thanksgiving.

  58. Emily R says...

    I’m dreading fall and winter. I’ve never been able to figure out how to have cute pants and warm feet. It’s like the combination does not exist. I look best in an ankle length pant, but tell that to freezing cold winter. I have big feet and look ridiculous in a bootie. I end up being miserable in Boston most of the year. Help!

    • Kim says...

      I feel you! I’m tall so most pants I own are ankle length whether I like it or not :) Have you tried skinnies with tall boots? I can wear black jeans to work so I do those with either black or brown boots depending on what I wear on top.

    • Catherine says...

      I’m in Texas, so our winter isn’t very cold, but I have dealt with the cold ankle issue, too. I finally decided to embrace it with black ankle pants, black wool socks, and black loafers. I also have size 10 feet.

    • Anonygirl says...

      Corduroys for pants. What about a fun oxford or mary jane for shoes?

    • Em says...

      Emily, I totally know how you feel! I’ve got long legs and larger feet, so most pants end up being ankle length for me (whether I want them to or not) and flat booties make my feet look clownish :-/ Winter is tough! My one solution has been wearing Chelsea boots with a ~1.5 inch heel… I find that raising my foot just a little bit can make it look smaller. And they look good with ankle length pants. Maybe that could work for you too? Good luck!

    • Allyson says...

      I think big feet + booties is great :) I have size 11 feet and love a big, chunky heeled bootie. I feel like it gives nice balance to my pear-shape. Booties are more fun with a cute & super warm wool sock. Really love Freebird booties in the Casey style. Amazing with skinnies or tights/leggings & a dress.

    • Sandhya says...

      Aquatalia lined booties and cashmere (not 100%, which frays) socks have been lifesavers for me, living north of you in NH. I also have big feet (size 11) and bunions that make most booties unwearable. This brand is expensive but so worth it. I would check out sales on Rue la la and elsewhere. I wore the booties throughout the winter, and since they are waterproof and have sturdy soles, they do well in snow and ice.

    • Kim says...

      I used to live in Boston years ago, and I’d say wear some layers! I used to wear tights and long johns under my clothes. Get some cool and warm wool socks.

    • Lauren says...

      I’ve decided to embrace wool socks this year. I also really like ankle length pants but figure I can pair them with a taller sock – even a patterned one. I prefer Chelsea boots or danskos but I think this could work with other shoe preferences?

    • Amanda says...

      I have big feet and feel fine in booties, I bet you’re the only one who thinks they look weird. But loafers or oxfords with nice socks are an option!

    • Emily R says...

      Thanks for all of the lovely suggestions! I think I just need to move to a warmer climate where I can wear beautiful shoes that won’t get ruined on a slushy commute to work and where I can let my ankles be free.

  59. Maywyn says...

    Love the floral dress!
    Me…Blazer sweater, plaid flannel shirt or tunic (unless i find a floral flannel), comfy jeans, earrings that won’t catch on my scarf, a new to me scarf, and, a styling umbrella.

    • Carly says...

      Please elaborate re: “styling umbrella”

      Intrigued!

    • Maywyn says...

      An umbrella with a neat pattern, like those at MOMA ( Museum of Modern Art) store. Vintage umbrellas are also a good source for patterns with style.

  60. Fern says...

    My best sartorial discovery was men’s cashmere cardigans. Menswear sweaters are always thicker and half the price. The best one I’ve ever found was a black cashmere cardigan by Joseph on The Real Real for like $60. It has (of course) giant pockets. As soon as it dips below 70 I move into that sweater and live there until the planet swings around and I find myself asking questions like “is this too heavy to wear as a swim cover up or nah?” And then I begrudgingly trade it for a cotton black cardigan.

    • Joana says...

      YES. I started buying men’s cardigans recently, and I have been SO SMUG about it. They have enough space in the sleeves to actually wear long sleeved shirts underneath without it being ridiculous, and yes — pockets! I fully support this!

    • yesss – most of my sweaters are hand me downs from men!
      i loooove fall dressing – it’s such a good transition and excited to stretch it out as long as possible! im still wearing my summer essentials (https://tps-steph.blogspot.com/2019/08/0045-summer-surviving-thriving.html) but adding my teddy fleece and perfect wool cardigan (both secondhand). so excited to add layers as it cools off even more. i also finally found the perfect cardigan (feels like a wool blanket and has pockets) at a yard sale this summer and cant wait to pull that out maybe with a layered dress and some booties (and obviously tights because upstate gets cold).

    • Mel says...

      YES I LOVE men’s sweaters! I love a good crewneck and I feel like I can never find the right one’s in the women’s section. I also prefer a looser fit so the men’s options are spot on. J. Crew men’s sweaters are some of my favorite. Also, love the poeticness of this line “and live there until the planet swings around”

    • Maire says...

      This is a totally genius tip! Especially since I like to wear things that are more oversized!

    • cate says...

      I thought I was the only one who had caught on to j crew men’s crew neck sweaters! I inherited some from my brother when he moved to a warm climate, and never looked back. That also started my love for j crew men’s button downs and straight leg jeans. They last so much longer than the women’s versions, and have a more classic, preppy style.

  61. Ellie says...

    I live in Florida so we don’t get much of fall, but I dream about this every year! Cozy sweaters, layers of blankets, the glow of the sun setting earlier, and all the scents! Fall is a deeply rich season. There’s a small chance that a move is in our future and I’m just praying it’s to some place with real fall!

    • Alex says...

      Ha! We’re moving from New York to Florida this year. I’m soooo looking forward to NO MORE WINTER! I too love fall, but it’s a sacrifice i’m willing to make for year-round beach weather. Good luck with your move!

    • Amanda says...

      We’re still in late summer mode here and I’m embracing it by tossing denim jackets and sweatshirts on with my summer clothes. But come fall, I’m busting out my beloved sweater blazer and booties, and thinking about trying to find a cute floral skirt for another option.