Fall/Winter Fashion

20 Casual Fall Outfit Ideas for 2020


I was going to post a Try-On Haul today, but I didn’t have much for that, and what I did have is selling out. SO! I decided to do a fall outfit roundup with casual fall outfit ideas that are easy to replicate. I hope it’s helpful.

Since most of us are living casual lives these days, these are all fairly casual looks, but most can be adapted for the work place or dressed up for church or date night. Just swap the jeans for pants, and maybe wear a dressier shoe, depending on your dress code or venue.

I linked the exact item if I had it; otherwise I linked to similar, but the idea here is to shop your closet, so hopefully it’s not too frustrating when you can’t purchase the exact pieces.

Also, if you’re new here, I’m 5’5″ and 135 pounds with an hourglass shape. I typically wear a 6 or 28 in pants and jeans, a small in tops, and size 8 shoe.


#1. Camel Cardigan w/ Dark Wash Jeans & a Statement Necklace

I love a camel sweater with just about any shade of denim, but I think it looks particularly sophisticated with these dark wash jeggings. See more in THIS POST.

I also have and like this J.Crew Factory option. It has a very similar style and fit, but it’s a darker shade of camel.

I feel like the necklace really makes this look, but it doesn’t have to be this exact one. Any chunky necklace that fits in the neckline would work to create a focal point and bring attention to your face.

What to Wear with Dark Wash Jeans This Fall | Fashion for Women Over 40

similar cardigan // tank // jeans (6P) // boots // necklace

#2. Black Sweater w/ Blue Jeans & Leopard Flats

In my opinion, you can never go wrong with a black top, blue jeans, and pop of leopard. This outfit is as easy to throw on as joggers, sneakers, and a sweatshirt, but it’s so much more polished and put-together.

mid-wash skinnies // black v-neck pullover // leopard loafers // gold hoops // layer necklace

#3. Joggers w/ Denim Jacket & Fashion Sneakers

Let’s face it, a lot of us are wearing joggers more lately, but they can look stylish and put-together if you wear them with a fitted jacket. Denim is my favorite, at least until it gets colder.

The fashion sneakers also help elevate this athleisure look, and don’t forget to accessorize!

denim jacket // stripe tee // joggers // fashion sneakers (similar for less) // earrings // necklace

Here’s another example, this time with a leather jacket and camo print tee.

This jacket is almost sold out, and I’m having a hard time finding a similar one with a hood, but Kohl’s and Magnolia Boutique have faux leather versions, and Express has one with the shearling trim that’s really of fun.

leather jacket options here, here and here // camo tee options here and here (v-neck option) // joggers // fashion sneakers (similar for less) // earrings

#4. Cardigan w/ Graphic Tee & Snake Print Sneakers

Cardigans can sometimes read frumpy, so one way to make a cardigan look a little more modern is to pair it with a graphic tee. I also like how the snake print slip-ons add texture and interest to the look.

My NYC graphic tee is from J.Crew last year, but they have a similar one this year. I sized up to a medium.

similar NYC tee (M) // black cardigans // similar rag & bone Cate ankle skinnies // Vince slip-on sneakers (size down half; more sizes avail in this year’s version)

I’ve also worn this graphic tee with my joggers and a denim jacket, another version of #3.

denim jacket //similar NYC tee (M) // Zella joggers // white sneakers // earrings // necklace

#5. Utility Jacket + Grey Tee w/ White Jeans & Taupe Booties

Yes, I wear white jeans in the fall, I love to pair them with a grey tee and an olive utility jacket.

I wore light beige suede booties with this look, but you can easily swap them out for fashion sneakers or loafers if you want to tone it down. I would just stick with a lighter color. See more in THIS POST.

Try This: Utility Jacket + White Jeans with Grey Tee and Ankle Boots

utility jackets // grey tee (M) // white jeans // grey booties (cloud suede) // earrings

#6. Cheetah Print Tee + Black Leather Moto w/ Black Jeans & Mules

Cheetah print is a nice alternative to leopard, and it pairs so well with black.

My ATM cheetah tee was a major splurge during the #NSale, but I found a really good Amazon look-alike for a fraction of the price (it’s the color A-leopard03).

leather jacket options here, here and here // similar cheetah tee // black jeans // black mules

And I swap out the leather moto for my denim jacket, for a less edgy look.

casual fall outfit ideas with a cheetah tee

#7. Boyfriend Jeans w/ Leopard Tee + Black Cardigan & Ankle Boots

It takes a really good pair of jeans to get me out of my skinnies, but the rag & bone Dre is a nice slim boyfriend fit, and they’re also on sale! Just be sure to size down at least one full size.

The cardigan with leopard tee keeps the look comfy and cozy, but I’m dying to put one of my leather moto jackets on top to give it an edgier vibe. See more of this look HERE.

casual fall outfit ideas with boyfriend jeans

black cardigans // similar leopard tee // boyfriend jeans // suede Chelsea boots

#8. Grey Sweater + Demim Jacket w/ Black Jeans & White Leather Sneakers

Black jeans with a grey tee and denim jacket is one of my go-to outfits, and one day it occurred to me to try it with a grey cashmere sweater. I really like the juxtaposition of the luxe sweater and casual jacket, and it’s warmer than a t-shirt on cooler days.

The white leather sneaker trend is perfect for this look, and the P448s would look amazing with this too. If you don’t like the white, you could also wear black sneakers or casual booties.

Jo-Lynne Shane wearing VEJA Esplar with black AG legging ankle jeans, Two by Vince Camuto Denim Jacket, and grey cashmere pullover

similar grey sweater // black jeans // denim jacket // sneakers

#9. Graphic Tee + Leather Jacket w/ Blue Jeans & Snake Print Shoes

I never get tired of leather jackets and jeans! Adding a graphic tee is a fun way to elevate this basic look and express your personality, and the snake print booties add pattern and texture.

I’ve also worn this with the snake print slip-on sneakers shown in look #4.

This grey leather jacket sold out, but you could easily wear a black one with this.

casual fall outfit ideas with a graphic tee

similar NYC tee (M) // similar leather jacket // similar raw hem skinnies // snake print booties

#10. Olive Utility Pants w/ Denim Jacket & Leopard Tee

Olive green utility pants are a nice alternative to jeans in the fall, and they pair so well with a denim jacket. These exact pants are 40% off right now, and they run TTS; they fit a little snug at first, but they loosen up quickly.

YOU MIGHT ALSO LIKE: 5 Ways To Wear Olive Utility Pants

My exact leopard tee sold out, but I found one at Amazon that is sort of similar. It’s the color Multicolor #3.

casual fall outfit ideas with utility pants

cargo pants // denim jacket // similar leopard tee // similar mules

#11. Grey Sweater with Black Jeans, Leather Moto & Fashion Sneakers

This luxe meets sporty casual fall look is one of my all-time favorites. I love the combination of black and grey tones, and the mix of patterns and textures. See more in THIS POST.

Luxe Meets Sporty: A Casual Monochromatic Outfit for Fall

grey turtleneck // black jeans // similar leather jacket // fashion sneakers (options here and here) // hoops

#12. Camel Pullover w/ Black Jeans & Leopard Shoes

Camel and black with leopard is a fail-proof combination, and this particular sweater has some nice details. Unfortunately, it’s not on sale at the moment, but keep an eye on it!

Again, I like to add a statement necklace with a camel top, since camel is so close to my skin color. I feel like it helps break it up, and draws attention to my face. This one is really pretty and goes well with olive and other earth tones as well as camel. It’s also on sale.

I would usually wear leopard pumps with this, to dress this up a bit more, but I wore these flats for an outdoor dining experience where I knew I’d have to do some walking. The pointy toe and small heel keeps them dressy enough to balance out the rest of the look, whereas a ballet flat would be a lot more casual.

casual fall outfit ideas with a camel sweater

camel sweater // black jeans // leopard flats (size 9) // necklace // earrings

Need to level up your athleisure game for a Zoom meeting? Swap out the jeans for joggers, and throw on some comfy slip-on sneakers. Or, if you want to wear your slippers, no one will be the wiser.

casual fall outfit ideas with joggers

sweater // joggers // snake print sneakers (more sizes) // earrings // necklace

#13. Camel Pullover + Black Quilted Vest w/ Blue Jeans & Pop of Leopard

Quilted vests are great layering pieces for fall. I am always amazed by how much warmth they add to a look, and they’re so much less bulky than a coat.

I love to add a pop of leopard print to a camel and black outfit, but this time I did it with a scarf and kept my shoes neutral. See more of this look HERE.

Casual Outdoor Dining Outfit for Fall with Puffer Vest and Leopard Scarf

camel pullover // skinny jeans // taupe ankle boots // similar leopard scarf // similar vest (option) // taupe tote // sunnies

#14. Taupe Suede Moto + Black Tank w/ Washed Black Jeans & Taupe Booties

This outfit is definitely a favorite from my 22 Days of Fall Fashion style challenge. The combination of taupe suede and washed black denim is unexpected but so chic, and the mixed metal statement necklace and the belt are details that shouldn’t be overlooked. See more in THIS POST.

Jo-Lynne Shane wearing a taupe suede moto jacket outfit for fall

taupe suede moto // black tank // similar jeans  // similar belt // booties (size up half; Tuscan taupe suede) // necklace // sunnies (option)

#15. Long Cardigan w/ Blue Jeans & Pumps

I love this outfit for a leveled-up casual look you can wear to meet friends for lunch, or to any business casual event.

You can swap the blue jeans for black jeans if you want to dress it up a bit for church or dinner out.

Or, if you’re at home all day on Zoom calls, just trade the pumps for slippers and maybe lose the belt, but definitely keep the necklace! See more in THIS POST.

casual fall outfit ideas with a long cardigan

cardigan // woven tank // blue jeans // snake print belt // black pumps // croc print tote // layer necklace

#16. Grey Turtleneck + Burgundy Puffer w/ Black Jeans & Black Booties

This is a look from 2018, but I’ve always loved it. The luxe cashmere turtleneck keeps the look polished, and the quilted puffer adds a sporty vibe, plus of course, extra warmth. See more in THIS POST.

Unfortunately, the layered look vest I’m wearing sold out long ago, but you can do a plain burgundy vest instead. I have this one in brown, and it’s a great vest for the price, very flattering.

A casual-cool fall outfit featuring a Marc New York burgundy hooded puffer vest with black Rag & Bone skinny jeans, booties, and a grey cashmere turtleneck. #falloutfit #fashion #fallfashion #outfit #fashionover40

similar burgundy vest // similar grey turtleneck // black jeans // similar black booties

#17. Black Leather Moto w/ Blue Jeans, White Leather Sneakers & Cashmere Scarf

This is an outfit I repeat in some iteration over and over again. I love the juxtapositions of luxe and sporty, casual and edgy.

FYI, I highly recommend this cashmere scarf. I wore it a ton the last two seasons. It’s thinner than some, and made of the softest cashmere, so you can wear it either as an outfit making piece or a cold weather accessory.

It’s easy to remove and slip into your tote when you don’t need it, but it takes an outfit up a notch if you’re going to be out and about running errands, etc. Oh, and it makes a great holiday gift too!

Jo-Lynne Shane wearing VEJA Esplar with AG Raw Hem The Legging Ankle Jeans, black Bernardo leather moto jacket, and Everlane cashmere scarf

 similar leather jacket // black v-neck sweater // skinny jeans // cashmere scarf // sneakers

#18. Drapey Moto Jacket + White Tee w/ Blue Jeans & Fashion Sneakers

This drapey faux suede moto is a softer and more comfortable than the heavier suede and leather jackets I typically wear, but I feel like it’s more flattering than a cardigan. It comes in 4 colors, and it’s under $100.

The fashion sneakers are a fun way to keep it modern, but of course booties or loafers would work too. See more in THIS POST.

casual fall outfit ideas with drape front moto jacket

drape front jacket // white tee // blue jeans // fashion sneakers (similar for less) // silver hoops // Victoria Emerson bracelets c/o // sunnies (similar for less)

#19. Ivory Sweater + Blue Jeans + Animal Print Boots

This is a super simple outfit combo that always works. If you don’t have snake print boots or shoes, I highly recommend getting a pair. They’re a great way to add pattern and texture to a simple look.

casual fall outfit ideas with cowl neck sweater

ivory cowl // similar raw hem skinnies // snake print booties

#20. Black Leather Jacket + Black Tee w/ Black Jeans & Snake Print Shoes

You can never go wrong with an all-black look, and I love the little touch of snake print in the shoes to add texture and pattern to the otherwise monochromatic outfit. See more in THIS POST.

casual fall outfit ideas with black leather jacket

leather jacket options here, here and here // Everlane ribbed tee (M) // black jeans // snake print mules // statement earrings

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29 thoughts on “20 Casual Fall Outfit Ideas for 2020

  1. Love this kind of post! I could pull together almost any of these looks from my closet and really appreciate the inspiration of combos I might not think of. It’s almost like having new clothes without spending the money. Thanks!

  2. Love this post! Thanks for the terrific summary. Saving it for future reference. Will need it when I’m stumped what to wear. You’ve inspired me to keep my gray t-shirt in my closet rather than summer clothes bin. Enjoy your day! Having either some down time movie night with hubby or a date night out sounds lovely. We are setting up a table at end of drive way with individually wrapped candies/ chocolates/ goodies for the Trick or Treaters (no reaching into a bowl). We will be sitting up on front porch to enjoy the cute costumes and youngsters from good distance. It may be different but we can still enjoy Halloween from a distance. At least there is no snow!

  3. Thanks for all the great fall style inspiration. I love when I can pin them and refer back to them when I have no idea what to wear. Happy Halloween 👻 and enjoy your dinner out tonight. 

  4. I really like this post, and pinned it to my Fall Fashion board. It will be great to reference when I need inspiration. For the items I don’t have, I have easy substitutions. Thank you!

  5. Have a good night. Yes things do change. My youngest of 3 has a bday today…. Halloween. He’s 26 today. Halloween use to be so full. His school bday and Halloween party then he brought home his friends for kid bday party then we took them all out trick or treating then home exhausted. Lol. Going to be quiet evening just us two also. Have fun. 

  6. Great post – I like how all of these outfits are in one place. I’m getting ready to pack for a trip next weekend (yeah!) and think I’m going to bring a few of these outfits.

  7. Did you size down in the black sweater in outfit #2? They say it’s over-sized and I was debating if I wanted to size down or not.

  8. Great outfits. You look so cute. You look great in skinny jeans. They still look so current the way you dress them. I hope they don’t go out. So easy to pair with shoes. 

  9. I know how you feel-two weeks ago we let our high school son attend a party; he rarely goes to parties and I was more concern with drinking and driving-a few days later we were told a kid  at the party tested positive.  I’m not going to lie, I kind of freaked out.  We waited 4 days and got him tested , the first rapid test was negative, then another test they sent out and took a few days also came back negative. Regardless he has to quarantine for 14 days.  

  10. Every time I see you in the fashion sneakers, it makes me want to go get a pair for myself. To me, that is my fav look, skiny jeans and sneakers! I’m in my late 30’s and am very active and fit, and sneakers keep me feeling young and in my sporty element. What do you think of the trendy high top sneaks or the wedge types? I am curious to see outfits with those since I don’t own any yet.

  11. Love those boyfriend jeans.  I’m considering them. .  .but the link is that for the same color your have styled?  They don’t look as blue on the Nordstroms site as they do on your blog.  I really like the shade on your blog.  Thanks!

  12. Hi- wondering what size you are wearing in #18- the drapey moto. Also,
    have you had issues with washing it or it turning your shirts a different color?
    Lots of reviews stating this.

    1. I should have written in there that I size up in BlankNYC jackets, and that one is a medium.

      I have not had any issues with color transfer but I usually wear it with all light colors. And I haven’t even washed it yet, so I can’t speak to how it washes up.

  13. Great post! I wanted your grey everlane cashmere scarf last year but it sold out by the holidays. They don’t have that color this season. What do you think about wearing the oatmeal with grey and black? Any other suggestions? Thank you!

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