You are currently viewing How to Style 6 Sweater Outfits for Fall – OOTW

It’s definitely been a weird week for weather. We had snow on Monday, huge amounts of rain on Wednesday evening and temps ranging from 33F to 71F (basically 0C to 22C). All I wanted to wear all week was a cozy sweater (and some days, a jacket on top!)

After about the third day of wearing sweaters, I noticed a pattern, so I decided to just go with it. I figured that it might be just the inspiration somebody needed to break out their favorite sweater.

Except, everyone has probably been waiting impatiently to do that anyways πŸ˜‰

I hope you enjoy these cozy outfits. I’d love to hear in the comments what your favorite look of the week was!

And as always, if you see something you like, I encourage you to look for it in the secondhand market first. For tips on secondhand shopping online, check out this post.


Outfit 1 – 10.18.2020

I loved this outfit. I wore it from the moment I got up (well after I did my hair and makeup) to the moment just before bed when I changed into pjs.

I’ve really been leaning towards comfy outfits that I can wear all day. For the longest time, I still tried to dress like I did pre-COVID and it made me feel good for a while, like not everything was so different.

Sweater Outfit 1 - a mirror selfie of a white woman with wavy blonde hair wearing a loose grey sweater with a ruffled hem over a black ruffled midi length dress with ruffles and silver polka dots. she is wearing black moto boots with silver detailing. The next 3 photos are closeups or different angles.

But I’ve come to accept that I spend 95% of my time in my house and while I still want to wear nice things, my wardrobe is definitely leaning more toward casual with a side of dressy, instead of the other way around.

I pay a lot of attention to detail when I put an outfit together. I don’t wear a lot of accessories so it’s really the details that make an outfit special for me.

In the case of this pairing, I love how the ruffled tier of the sweater compliments the ruffles on the dress. It makes the outfit feel fun…so fun that I was even caught twirling in the kitchen in this outfit. You just have to when you wear a swishy dress/skirt, right?!? πŸ˜‰

I pretty much only wear these black moto boots with silver detailing whenever I wear this dress. The silver detailing on the skirt pairs perfectly with it.

I also love how that there are 2 style ideologies going on here…the softness of the sweater (literally) and the dress, contrasted with the toughness of the boots.

This outfit felt really good and something that I would definitely wear again!


\\ Outfit //

Secondhand Minnie Rose Cashmere Sweater

Secondhand Rebecca Taylor Silk Dress (via The Real Real)

Frye Harness Boots


Outfit 2 – 10.19.2020

Not gonna lie, this was probably my favorite outfit this week. I’ll probably wear it again this weekend.

I’ve always been a fan of blue but I have come to love it even more lately. After my recent foray into color, which I had a lot of fun experimenting with, I think I’ve found a way to incorporate it into my wardrobe in a more subtle way for fall and winter.

I’ll still be wearing my rainbow coat, but I’ll definitely be saving the other more colorful pieces for the warmer months.

Sweater Outfit 2 - a mirror selfie of a white woman with wavy blonde hair wearing a blue crew neck sweater over a blue pleated waist dress. She has a grey scarf tied around he neck and is wearing black combat boots. The next 3 photos are closeups or different angles.

I’m not a huge fan of tights so I often wear workout leggings underneath my dresses. These happen to be cropped but I’ll switch to full length when it gets colder.

In the warmer months I usually wear a light shoe with the dress but I really like the contrast of the lighter blues with the black of the boots.

The pleated skirt of this dress is one of my favorite features. This dress has a drop waist and I think this sweater sits at the perfect spot without manipulation.

This was one of the colder days that we had (the one where we got snow), so I added one of my favorite vintage wool coats that I ordered from Etsy 2 years ago.

I added this grey satchel handbag because I liked how the structure of it kind of mirrored the structure of the coat. I also liked how the black strap coordinates with the boots.

Sweater Outfit 2 - a mirror selfie of a white woman with wavy blonde hair wearing a blue crew neck sweater over a blue pleated waist dress. She has a grey scarf tied around he neck and is wearing black combat boots. She is wearing a grey overcoat and has a great handbag over her arm.

This is handbag that I “won” at a a silent auction last fall. If you’re interested in the other handbags that I own, be sure to check out this post.


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Thrifted Everlane Angora Sweater

Secondhand Mansur Gavriel Cotton Dress (via The Real Real)

Secondhand Lululemon Align Leggings

Dr. Marten’s Leona Boots

Vintage J.G. Hook Wool Coat (via Etsy)

Botkier Satchel


Outfit 3 – 10.20.2020

I thrifted these pants about a month ago and I have been dreaming of this combo ever since!

I love the look of a pair of tighter fitting pants with an oversized long sweater. It’s definitely a combo that I used to wear a lot a while back but not so much anymore so it’s nice to revisit it.

These pants have a button detail at the hem. If I wear them with hiking boots (which I did later this particular evening to walk the dog), I button them up. But with these particular boots, I unbuttoned them to let them rest outside the boots.

Sweater Outfit 3 - a mirror selfie of a white woman with wavy blonde hair wearing a cream crew neck long sweater over a pair of tan pants. She has a grey scarf tied around he neck and is wearing brown suede boots. The next 2 photos are closeups or different angles.

I added my silk hankie and my gold pendant and necklace. Since lightening my hair, I find it helpful to have something with a little color at my neck if I’m wearing a cream colored sweater. I think it adds a little contrast so that the hair doesn’t blend into the sweater as much.

I don’t want to stop wearing some old favorites that I had when my hair was darker, so I find that I have to find a different way to make them work for me.

My green plaid wool coat was the perfect topper since it also has creams and browns in it. This may top the list as my favorite purchase of 2020. I put it on my favorites list during the summer and let it stay there for a few months before getting it as an anniversary gift (I hinted very heavily that I really liked it πŸ˜‰).

Sweater Outfit 3 - a mirror selfie of a white woman with wavy blonde hair wearing a cream crew neck long sweater over a pair of tan pants. She has a grey scarf tied around he neck and is wearing brown suede boots. She has added a long checked wool coat that has green, cream and tan colors.

I decided to use my caramel colored vintage Coach handbag since it goes so well with all of the other warm toned items in this outfit.

Same outfit but showing the tan handbag.

\\ Outfit //

Eileen Fisher Cashmere Sweater

Secondhand Ralph Lauren Sport Pants

Ozma of California Silk Hankie

Secondhand Free People Suede Boots

Secondhand Rodjeber Wool Coat (via The Real Real)

Vintage Coach Handbag


Outfit 4 – 10.21.2020

I left the house pretty early on this day and wanted an outfit that was easy. My black silk jumpsuit and combat boots was the first thing I thought of. I tried a couple of other sweaters before settling on this thrifted sweater from about a month ago.

Sweater Outfit 4 - a mirror selfie of a white woman with wavy blonde hair wearing a red crew neck long sweater over a black jumpsuit with black combat boots. The next 4 photos are closeups or different angles.

My favorite accessory of the day was my “I voted” sticker. In hindsight, I probably should have worn Tuesday’s outfit. IYKYK πŸ˜‰ But at least it matched my sticker. Have you voted yet?

I’ll never get sick of looking down at these boots!

My favorite thing about this sweater is the slit on the side. When I brought it home, it had this awful red and white striped layer so that it looked like there was a longer top underneath. Using my seam ripper, I got rid of that and it made the sweater 1000% better!

This backpack continues to be one of my favorite bags. I’ve had it for about 5 years I think and it’s leftover from my fast fashion days. And although I’ve gotten rid of a lot of stuff from that time, I did make some good choices that have stayed with me.

\\ Outfit //

Secondhand Ralph Lauren Cotton Sweater

Elizabeth Suzann Silk Mara Jumpsuit

Dr. Marten’s Leona Boots

Margot Backpack


Outfit 5 – 10.22.2020

This is definitely the kind of outfit that I am craving right now…comfy and effortless.

Sweater Outfit 5 - a mirror selfie of a white woman with wavy blonde hair wearing an oatmeal crew neck sweater a pair of caramel colored pants and leopard print boots. The next 4 photos are closeups or different angles.

I think there’s and ease and effortless vibe to a monochromatic outfit. And normally I reserved the term “monochrome” to items that match perfectly but I think it works here for these 2 items in similar tones.

I love the softness of this cashmere sweater. It was pretty warm outside today but this was the perfect outfit for temperature control. I will always sing the praises of natural fabrics.

I’ve only been aware of how great clothing made from natural fabrics is for the past few years but I could never go back to synthetic fibers again. You can read more about natural fabrics in this post.

I think I shied away from natural fabrics like silk and cashmere for a long time because they were out of my price range. But once I discovered how much natural fabric clothing I could find in the vintage and secondhand market, there’s been no turning back!

Another thing I never get tired of looking down at is the pockets of these pants. I’ve been thinking lately that I need to make another pair of these soon…I’ll just add it to my growing list of projects that I have no motivation to start! I’m really hoping that changes as it gets colder.

Even though I love this sweater and pant combo, it was feeling a little bland. So I added my leopard print boots! And my backpack. I love how the black and brown of the boots pull in the black from the bag and the brown from the rest of the outfit.


\\ Outfit //

Secondhand Eileen Fisher Cashmere Sweater (via Eileen Fisher Renew) – gifted Fall 2019

Sew Liberated Arenite Pants (sewn by me)

Huma Blanco Ortencia Boots – gifted Fall 2019

Margot Backpack


Outfit 6 – 10.23-2020

When I bought this dress over the summer, I knew that I would wear it more in the colder months with layers.

It’s actually a vintage nightgown. It’s silk and there’s a definite sheerness to it. When I bought it, I knew that it would be perfect under sweaters and blazers.

Sweater Outfit 6 - a mirror selfie of a white woman with wavy blonde hair wearing a dark grey mockneck sweater over a light grey dress with black combat boots. The next 4 photos are closeups or different angles.

I tried a different grey sweater before this one but the proportions were off. The cardigan that I tried was too long and I wasn’t in the mood to manipulate the length today so I grabbed this vintage cropped wool turtleneck.

I don’t really love turtlenecks so I always turn the neck inwards and roll it down so that it creates a mock neck effect.

One of my favorite details of this dress are the little lace inserts on the sides and I’m glad that this sweater doesn’t hide them.

It’s chilly here today so I added a pair of full length leggings that I tucked into socks. These are old ones from my fast fashion days and I hope they never wear out! I decided to wear my combat boots because I like the extra clearance it gives me between the bottom of this dress and the floor.

And here’s my trusty backpack…again πŸ™‚

This dress is fairly delicate. In the past, I would not have worn it for fear of ruining it. But one behavior that I’ve really tried to change over the past few years is that I no longer save things.

I try to wear everything that I own and to not be precious about it. I reason that if something happens then I can figure out a cleaning or repair solution.

Would you wear a silk nightgown like this for everyday wear?


\\ Outfit //

Secondhand Poetry Wool Sweater

Vintage Janet Reger Silk Nightgown (via Narrations LDN)

Lululemon Align Leggings

Dr. Marten’s Leona Boots

Margot Backpack


Have you started breaking out the sweaters yet?

What’s your favorite kind to wear? As you can see, I’m a pretty big fan of crewnecks.

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Until next time,

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This Post Has 2 Comments

  1. Kate

    Hey! Great ideas for the sweaters. You know, I think the best thing about your outfits that I can learn from is how you do footwear! You always seem to add a bit of sass or danger with the feet! I think my footwear is all too safe and β€˜nice’ when I actually love the vibe of the grungy biker / cowboy boots you add to an otherwise feminine outfit. I need to try this but don’t want to rush out and buy big new boots.

    1. Gillian

      Thank you Kate! And I’m so glad that I’ve inspired you to try some fun footwear! I keep my wardrobe pretty neutral and I have found that fun shoes and accessories really help to make it feel more exciting! Good luck!

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