Fall/Winter Fashion
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Shop Your Closet: 25 Fall Outfit Ideas

I created a roundup of fall outfit ideas a couple years ago, and it’s been updated and republished a few times. When I went to update it again for this year, I realized how dated most of those looks are!

Isn’t it funny how we go along and styles are sort of similar for a few years, and then all of the sudden they go through a pretty big evolution? I feel like that’s where we are this year.

So I went ahead and started over from scratch, although I did pull a few looks from that original post that I feel are still relevant… and because I’m an overachiever, I came up with 25 fall outfits this time!

Shop Your Closet: 25 Fall Outfit Ideas to copy right now

Since most of you say you live pretty casual lives, I’m going to stick with more casual looks, but a lot of these 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.

25 Fall Outfit Ideas

I did my best to link similar styles for the items that have sold out, but the idea here is to shop your closet, so hopefully it’s not too frustrating when you can’t purchase the exact pieces.

#1. White Tee + Olive Cargo Pants + Denim Jacket + Snake Print Sneakers

This outfit in one version or another has been on constant repeat since last spring when I got these pants. But of course, you can wear any olive cargo pants and recreate this look. This pair is really good and a fraction of the price.

Don’t have snake print sneakers? White works too.

similar white tee // denim jacket (exact) // cargo pants (option) // Vince leopard slip-ons (this year’s version; budget option) // Neverfull

#2. Stripe Turtleneck + Black Quilted Vest + Black Skinny Jeans + Fashion Sneakers

This outfit is from several years ago, and I still wear it, although now with my Veja sneakers because I passed my Adidas down to my daughter.

Also, this tissue turtleneck is a great layering piece for fall and winter. For size reference, I take a small.

striped turtleneck (exact) // quilted vest (exact) // black jeans // Adidas Superstars // burgundy backpacks

#3. Camo Tee + Ivory Cardigan + Blue Jeans + Chestnut Booties

Camo is trending this year in a major way, and this tee is soft and comfortable. I love it with the ivory sweater; but grey, navy or black would also work just fine.

camo tee // cigarette jeans // similar ivory cardigan // neutral booties // neutral tote

#4. Black Sweater + Black Denim Jacket + Blue Jeans + White Sneakers + Grey Scarf

This is an outfit I wore a few times early last spring when it was still cold here in Philly, but it works for fall too.

I cannot wait to break out this scarf again, I wore it a ton last year. It’s thinner than some, and made of the softest cashmere. (Makes a great holiday gift too!)

FYI, this v-neck cashmere sweater is on sale for $59 TODAY ONLY at Lord + Taylor! I recommend sizing up; I have the medium.

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 // grey scarf (exact) // sneakers (option for less)

#5. Camel Turtleneck + Teal Puffer Vest + White Jeans + Brown Riding Boots

I think this outfit is really fun with the white jeans, but if you don’t like wearing white in the fall, black or blue would also work with a teal vest and camel sweater.

And I was super excited to find this vest still available at Amazon this year. It’s really soft and lightweight, and very flattering on. It’s not as bright as it photographed here; it’s more like the color on the website. For size reference, I take a small.

packable vest (exact; mine is the cold green) // similar camel turtleneck // white jeans // Frye riding boots in whiskey

#6. Black Tank + Grey Jeans + Light Grey Cardigan + Snake Print Booties

Monochromatic looks are timeless and always classy, and they’re also trending at the moment. I like the combination of the light grey sweater and darker grey jeans, and then the snake print booties add a nice bit of color and texture to the look.

I wore a black tank here, but it also works with a white tee for a more casual vibe.

light grey cardigans // black shell // similar grey jeans // snake print booties // necklace

#7. Black Top + Blue Jeans + Animal Print Flats

You can’t go wrong with black and denim and leopard. This exact blouse is out of stock, but you could totally do this with a black sweater.

black blouse // skinny jeans // leopard flats (more options) // black quilted tote // sunnies

#8. Grey Sweater + Black Jeans + Denim Jacket + 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 — my P448s would look amazing with this too. But if you don’t like the white, you could also wear black sneakers (how fun are these!?!) or booties (something casual like this.)

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 (option)

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

This is another very 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 an outfit in a subtle way.

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

#10. Green Quilted Vest + Stripe Tee + Blue Jeans + Leopard Flats

This is another outfit from a few years ago that I would totally wear this season, and this stripe tee is still available!

The J.Crew Factory artist tee is one of my favorite layering pieces. The ballet neckline is more flattering than a traditional crew, and the slub cotton material is thicker than most (not see-through at all) and fits close to the body without clinging.

similar vest // stripe tee (exact) // skinny jeans // leopard flats

#11. Camel Turtleneck + Dark Wash Jeans + Plaid Coat + Cognac Loafers

While this is more conservative than most of my looks, I’m kind of digging the preppy vibe. Even without the coat, it’s a simple and pulled-together look that you can wear so many places.

Not a loafer fan? Booties or ballet flats work too.


plaid coats // similar cashmere turtleneck // dark wash skinnies // leather loafers (exact – so comfy!)

#12. Snake Print Blouse + Black Jeans + Black Booties + Taupe Moto Jacket

A blouse is such a fun way to participate in the snake print trend without breaking the bank. I love how this one looks with black pants and a taupe moto, but you could also do black trousers and a taupe/beige blazer for the work place.

snake print blouse (option) // black jeans // similar moto jacket // similar booties

#13. Camel Sweater + Black Quilted Vest + Blue Jeans + Burgundy Flats + Plaid Scarf

Here’s an oldie but goodie! I loved this look — I still remember getting excited when I created it.

A camel sweater is such a great closet basic; this time I’m wearing a crewneck style, but a turtleneck would work too. Unfortunately the scarf is old, but you could do this with any plaid scarf.

similar camel sweater // similar quilted vest // skinny jeans // similar flats // plaid scarf options

#14. Leopard Pullover + Black Leather Jacket + Black Jeans + Black Booties

This is another look I shared recently, and it’s very simple. Any printed top will work with an otherwise all black outfit.

How to Wear Crop Pants in the Winter with Sock Booties

 similar leopard sweater // black crop jeans // similar leather jacket // similar booties // black satchel

#15. Ivory Sweater + Olive Jeans + Cognac Boots

I love this simple color combo for fall. The key to making a very simple outfit like this look polished is to make sure the fit and proportions are on point, and accessories help too. I wore a layered necklace to create a focal point.

similar sweater (option for less) // olive jeans // camel boots // similar necklace

#16. Grey Turtleneck + Burgundy Puffer + Black Jeans + Black Booties

Super simple, but again, the fit and proportions are on point; and the luxe cashmere turtleneck keeps the look polished.

My layered look vest sold out, you can do a plain burgundy vest instead.

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 // black booties

#17. Grey Sweater + Light Wash Blue Jeans + Black Leather Jacket + Black Booties

Here’s another variation on the denim, grey, and black combo. (I did black pants, denim jacket, and this same grey sweater for #8 above.)

similar grey sweater // similar leather jacket // straight ankle jeans // similar booties

#18. Pastel Sweater + White Jeans + Grey Mules

You may not think about pastels for fall, but I think it’s fun to wear colors that are a little unexpected. Keeps things interesting!

lavender sweaters here and here // white jeans // grey shoes

#19. Graphic Tee + Blue Jeans + Snake Print Booties + Leather Jacket

Nope, 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.

graphic tees // grey leather jackets // raw hem skinnies // snake print booties

#20. Evergreen Sweater + Black Jeans + Black Boots + Leopard Clutch

This outfit is a little more wintry, but of course you can wear it in the fall too. You could also wear a brown boot to break it up, but I like the way the black knee high boots on black jeans create a long, lean leg line.

Here’s a similar sweater, and how pretty is this turtleneck poncho? I’d wear it over a black long sleeve tee with these jeans and boots.

evergreen sweater // black jeans // black boots // leopard clutch (option)

#21. Black Sweater + Black Leather Jacket + Dark Wash Skinny Jeans + Black OTK Boots + Red Bag

It doesn’t get much more basic than black and denim with a pop of red, but there’s something super chic about this look that I love. The leather jacket adds an edgy vibe, but you could wear a black blazer if you wanted a more conservative look.

similar jacket // black v-neck sweater // dark wash skinnies // OTK boot options // red crossbody

#21. Camel Turtleneck + Dark Wash Skinnies + Tall Brown Boots + Blue Wool Coat

And here’s yet another simple outfit with jeans and a camel cashmere sweater. This blue coat is gorgeous on the camel, but any color wool coat would work here — grey, red, white, black… anything works with camel and denim.

Update your winter outerwear wardrobe at the Lord & Taylor Friends & Family Sale: Save an extra 30% on Kenneth Cole REACTION Stand-Collar Boucle Coat, cashmere lined leather gloves, AG Farrah high rise ankle skinny jeans, Essential Cashmere Turtleneck Sweater, and Aerosoles Hashtag Tall Leather Boots #ad #lordandtaylor #womensfahion #winterstyle

camel turtleneck // dark wash skinnies // similar coat // brown boots

#22. Ivory Mockneck + Taupe Moto + Blue Jeans + Snake Print Booties

I tend to wear darker neutrals, but I really love this ivory and taupe combo with the lighter wash denim. The lighter print snake print boot is fun too, although I didn’t keep these because they weren’t very comfortable.

Jo-Lynne Shane wearing Dolce Vita Coltyn Snakeskin Booties, AG Legging Ankle Jeans, BlankNYC Suede Moto Jacket Midnight Toker, and Madewell Inland Turtleneck.

ivory mockneck // similar moto jacket // skinny jeans // snake print booties

#24.  Oatmeal Sweater + White Jeans + Taupe Boots

And here’s another outfit with a combination of light neutrals. You could also do this with white cords.

similar ivory cowl // white skinny jeans // taupe boots (option) // tote

And finally . . . I couldn’t do this post without dredging this one up from the archives.

#25. Yellow Cardigan, Leopard Scarf, White Tee, Blue Jeans, Brown Ankle Boots

If you found my blog from this outfit on Pinterest, raise your hand!

Undoubtedly my most pinned outfit of all time, this mustard cardigan with the leopard scarf and bootcut jeans is still relevant.

Sure, rises have gotten higher, and infinity scarves have given way to more traditional styles, but I would totally wear a more modern iteration of this outfit right now. In fact, I put one together for you!

leopard scarf // yellow cardigan // white tee // brown ankle boots // bootcut jeans // brown belt

That’s a wrap! I hope these fall outfit ideas help you expand your closet and get more wear out of what you already have.

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102 thoughts on “Shop Your Closet: 25 Fall Outfit Ideas

  1. Love this! Lots of outfit inspiration here! I love your style. It’s so accessible. I really enjoy when you put this type of post together. I find them to be very helpful.

  2. Great post! I would love to know which outfits you threw out from last year or the last couple of years that are dated now. 

  3. Wow!
    Love them all!
    My question now that we are
    having snow today …ughhh!,,
    Do you not wear short jackets and 
    Trade for heavier sweaters and coat.
    Too cold too soon here!
    Fall come back!
    Always notice you hv great boots!

    1. Yes, these are fall outfits. For winter, I definitely wear a heavier coat. 🙂 Well, I still wear the wool ones sometimes, over turtlenecks and warm sweaters. When I wear leather or moto in winter, I wear over cozy knits, but here in Philly we don’t get nearly as cold as Chicago… or when we do, it doesn’t last long.

  4. Hi JoLynn!  I have been a reader for many years, but have never commented before.  I LOVE, LOVE, LOVE this post.  I am retired, so lead a fairly casual lifestyle now.  This post is absolutely perfect and came at a great time since we will be travelling soon.  Thank you for all you do, it is much appreciated.  Pat in Nevada

  5. OMG, Jo-Lynne, this post is SO helpful!!! Thank you so much for all the work, thought, photography, links, and helpful descriptions and tips you put into this post! As someone on a modest budget who is still (in her 40’s) paying down hefty student loan debt, I need to focus more on shopping my closet than on shopping in stores or on line. It can be hard when drinking from the fire hose of new trends each season to a)keep from overspending, and b)come up with fresh outfit ideas that feel inspired, fun to wear, and relevant (if that happens to be a concern). So posts like this one are pure gold and become a resource I return to again and again for trusty outfit formulas that I can plug my existing wardrobe items into during my morning “get-ready” rush, and know I will come out with an outfit that works and feels fresh. I am repeating myself here and gushing for sure, but thank you, thank you, thank you for creating this post. I know it must have taken a lot of time and effort, and I appreciate that!

  6. Yeppity yep. It’s #25. I wear it with deep wine skinny jeans. Will be wearing it tomorrow..👍🍁🍂

  7. Great post JoLynne!  I love these kinds of posts,  I am terrible at actually putting outfits together!  So many times I actually have the pieces but just haven’t paired them together yet!  This really helps.  Also just wanted to tell you I love your haircut in the last pic,  really flatters your face well!

    1. Thank you, that was like 7 or8 years ago. I’m not even sure what was different, as it’s a similar length and cut. but it does have a different shape. (It was a different hair dresser.)

  8. This was a great post! You have really encouraged me to be just a bit more extra! Even casual, there’s no need for me to be lazy and leave off the vest or layered necklaces, etc. My only issue is that winter seems to have set in early in CO, and I can’t wear the cute tank under a jacket without freezing, so I am shopping my long-sleeved closet. Thank you!

    1. Are you calling me extra??? 😂 Haha, kidding. I agree – adding some jewelry or a vest really does amp up a casual look with very little effort. And yeah, these outfits were intended for fall. For winter, I definitely would be using long sleeves as under layers and chunkier knits in general.

  9. This post is amazing. So inspirational. Thank you for showing us that if we buy items that fit well and are of quality, we can wear them for a couple seasons with minor tweaks. Thank you for showing us how to shop our closet. 

  10. This post is fantastic, so many great ideas!  It doesn’t get extremely cold where I live so I can use this for inspiration pretty much all winter.

  11. I’m late to the party, but like many others I LOVE this post.  I will be referring back to you so that I can create new outfits with items in my closet.  This post contains so many great ideas!  A post showing what makes an outfit dated and how to make a change to make it current, would be fabulous!  I don’t know the easiest way for you to compile this type of post, but I have one idea.  Use a picture of an outfit from a recent photo by Alison, then change something that would make the outfit dated and take an at home selfie, showing the difference.  Enjoy the rest of your day!

  12. Loved all of the outfits and yes the last one with the bright yellow sweater really popped. But I have to mention this- does anyone other than a millionaire really pay over $500 for a pair of those Golden goose sneaks? If I can call them sneakers??
    Yikes oh my – not in my budget no way no how!

  13. Great reminder to combine what I already have in my closet. I so love fall and fall colors! Thanks for this!

  14. Great post! Like many others would love a “ Why is this outfit drafted” post where you just post pics of old outfits and explain why they are dated abd ways to update! 

  15. Awesome post! I like #13 the best, even though every outfit is spot on! It’s just something about that plaid scarf (I’m a big fan of scarves) with the sweater, vest and wine shoes that jumps out at me!! I must say that I could figure out what you would say needs “tweaking” for 2020 in many of the older posts. We are good students! HA HA!!

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