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How I’m Styling Some Comfortable Fall Basics/Classics To Look Fresh In 2021 – My Current Fall Uniform

I’m a lover of all seasons (like all styles) but fall fashion is by FAR my favorite and I know I’m not alone. One of the reasons is that fall ‘style’ doesn’t really change too much – it’s always cozy layers and denim, mostly basics that can just be styled or supplemented to look cool. Or so I’ve tried. So I shopped my closet (and added a few things) to pull together what feels like a pretty comfortable and yet not totally boring fall capsule collection. We are talking chore coats, cardigans, denim on denim, hits of stripes, and leather. Also, I’m definitely leaning into some grandpa and commercial fisherman vibes here and I’m pretty darn into it.

The Portland Grandpa

Hat | Sweater | Button Up | Vintage Jeans | Bag | Boots (similar)

I think Mal might have laughed out loud when I sent her this one, because yes it’s very Portland. Here we have a vintage cardigan and hat that I got at an antique Mall (wassup Stars in Sellwood). It’s an EXCELLENT cut, but if you are in the market, Alex Mill also has a bunch that are awesome. The denim shirt is Target (Universal Thread) and the cut/drape is really good – I feel like I’ve worn it a ton the last two years. I like it buttoned all the way to the top with the sleeve poking out under the cardigan (it’s thin and drape-y so it’s especially easy to layer under). The Levis are vintage and even a big baggy (I did it!!!!) that I rolled them up which I haven’t done before. I think one of my favorite things is the purse strap from Madewell that really added something special. The boots were from my boot roundup a couple years ago and they tuck in really nicely into the pants which is crucial, but here are some that are similar.

1. Plaid Bucket Hat | 2. Felt Bucket Hat | 3. Bucket Hat | 4. Bucket Hat | 5. Plaid Print Wool Blend Bucket Hat | 6. Corduroy Bucket Hat

1. Nico Chunky Cardigan in Upcycled Yarn | 2. The Sinclair | 3. Kailyn Cardigan Sweater | 4. Bayberry Cardigan Sweater in Buffalo Check | 5. Cassa Cardigan | 6. The Texture Cotton Cardigan

1. The Snapshot Leather Crossbody Bag | 2. Dome Crossbody Bag | 3. The Knotted Crossbody Bag | 4. The Sydney Zip-Top Crossbody Bag in Colorblock | 5. The Transport Saddlebag | 6. Naha Black Phone Mini Crossbody Bag

Head to my jeans review post for my current-ish picks:)

The Sloppy Hipster

Beanie | Shirt | Sweats | Jacket | Boots

Now Brian thought this look was funny, but I’m into it. That rugby shirt is a new addition and I LOVE it but was having problems styling it. I think it’s definitely a dress it down sort of situation so once I paired it with my sweats I liked it so much more. Then shoved said sweats into the boots and I was VERY into it, but I literally have no idea what is in fashion right now (and don’t like a lot of it) so this might be dumb. The oversized beanie is AWESOME, from Urban and the sherpa Levi’s Jacket I’ve had forever (and is a classic fall staple). And listen if you aren’t into “dressing up sweats” I get that, but I am and I really like them in these boots.

1. Knit Cuffed Beanie | 2. UO Short Roll Knit Beanie | 3. Re)sourced Cotton Cuffed Beanie | 4. Four-Stitch Shaker Beanie. | 5. Cuffed Beanie | 6. (Re)sourced Cotton Cuffed Beanie

1. Tiger French Terry Rugby Shirt | 2. Rudie Oversize Rugby Stripe Shirt | 3. The Shrunken Henley | 4. Peyton Rugby Tee | 5. Aerie Long Sleeve Cropped Polo T-Shirt | 6. Polo Ralph Lauren Varsity Stripe Rugby Top

1. MWL Breeze Skinny Joggers | 2. Live In Pocket Joggers | 3. French Terry Lounge Cargo Jogger Pants | 4. On The Road Pants | 5. MWL Superbrushed Easygoing Sweatpants: Striped Trim Edition | 6. Perfectly Cozy Lounge Jogger Pants

The Denim On Denim And “Just Add Stripe”

Beanie | Stripe Shirt | Jacket | Jeans | Boots

This one is a bit more basic – denim chore coat over skinny denim (both Madewell) with the same boots. The shirt has a really cute mustard collar which shakes it up and again I like the sleeve popping out under the coat. What you can’t see well is the classic navy bandana which I think was necessary to break up the same/same ness.

1. Chore Jacket | 2. Relaxed Patch Pocket Corduroy Jacket | 3. Denim Oversized Chore Coat | 4. Military Shirt Jacket | 5. Utility Denim Jacket | 6. Shirt Jacket

1. The Turtleneck | 2. The Modern Breton Tee | 3. Whisper Cotton Turtleneck in Herrick Stripe | 4. Striped Long Sleeve French T-Shirt | 5. Whisper Cotton Rib-Crewneck Long-Sleeve Tee in Mulford Stripe | 6. Modern Stripe Crewneck T-Shirt

1. Oversized Bandana | 2. Lotus Paisley Print Bandana | 3. Organic Cotton Print Bandana | 4. Cotton Bandana in Gingham | 5. Bandana Set | 6. 2-Pack Triangle Bandanas

1. Sharnell II Waterproof Knee High Boot | 2. Sadie knee-high boots in leather | 3. Phrancie Boot | 4. Melissa Button Inside Zip Leather Boot | 5. The Winslow Knee-High Boot with Extended Calf | 6. Melissa Harness Pull On Tall

The “Sun Just Came Out But It’s Still Muddy” Look

Sweatshirt | Shirt | Shorts | Boots | Socks

Welcome to the pullover I’ve worn 3-4 times a week (seasonally) since last fall. The Great just launched a couple new colors, which I don’t love as much as this one but the cut is my favorite. I put it over a striped mock turtleneck (Madewell) and added some striped socks (Urban) with my new duck boots (that I’ve since fallen in LOVE with from L.L. Bean). Obviously, I wore one of my million Levi shorts which never go out of style (ish).

1. Oversized Quarter-Zip Pullover | 2. French Terry Quarter-Zip Lounge Sweatshirt | 3. Soft Fleece Half-Zip Sweatshirt | 4. Camile Pullover | 5. MWL Airyterry Half-Zip Tunic Sweatshirt | 6. Quarter Zip Sweatshirt

Head to our shorts review post for the team’s favorites!

The “Are We Doing A Turtleneck Under A Sweatshirt?” Look

Turtleneck | Sweatshirt | Jeans | Shoes

I’m not a HUGE fitted turtleneck person because of my larger lovely ladies, but this one is boxier, with a dropped sleeve and a stiffer open neck. I LOVE IT (from Kule). I put it under my other zippy that I’ve been wearing a ton of (Alex Mill). I think the stripe is too much with my Vans, but I liked the flared jeans so I wanted to tuck the sweatshirt into that.

The “Neutral But Not Boring” Look

Beanie | T Shirt | Jacket (similar) | Jeans | Boots

Just when I thought that my favorite jeans (going on four years) were out of style (from Moussy) I rolled them up and boom, we are back. I LOVE the cut/drape of that t-shirt in boxy thin fabric. It has a wide neck and slouches just perfectly (Sundry is made in LA, too). I added some thick mens socks from Target, my Dr. Martens (that I obviously call Doctor Martens), with my classic bandana, beanie (Urban), and sherpa jacket (old but here is a similar).

1. Backcountry Sherpa Trucker Jacket | 2. (Re)sourced Sherpa Zip Jacket | 3. Sherpa Work Jacket | 4. Cropped Sherpa Utility Jacket | 5. Sherpa Liner Jacket | 6. Sherpa Bomber Jacket

The Sweatshirt “Onesie and Donesie”

Sweatshirt Jumper | Hat (similar) | Bag | Shoes

You bet I’ve been wearing the hell out of this. My stupid camera is blocking the zipper collar which is the same as my sweatshirt above, but it’s SO GOOD. It’s a heavy material so it drapes (doesn’t cling) and yet the cuffs are strong so it stays up styled like this. I’ve worn it with Vans, my Doc Martens and new Bog rain boots and it always looks cool. It has a drawstring that adds some shape, too. It’s a 10 out of 10, y’all.

1. Comfy Knit Jumpsuit | 2. Finn Jumpsuit | 3. Butter Wrap Jumpsuit | 4. MWL Breeze Drawstring Jumpsuit | 5. Lindsay Sweater Jumpsuit | 6. x goop Windbreaker Performance Jumpsuit

The Commercial Fisherman Cozy Vibe

Beanie | Shirt | Jacket | Sweats | Socks | Boots

Yep. I’m leaning into this in every way. The jacket (Madewell, from last year) is longer than I usually like to wear, but I like it here. I layered it over my old denim thin shirt (from The Great, similar here) and then with some sweats. I think the stripe on the socks with the duck boots are my favorite part, but those sweats fall down too fast, so next time I’d get a stronger bottom cuff to assure that my socks can be seen by all.

1. The Oversized Trucker Jean Jacket in Hunton Wash | 2. Denim Oversized Chore Coat in Laurelton Wash | 3. Denim Jacket | 4. Ex Boyfriend Trucker Jacket | 5. Denim Trucker Jacket | 6. Shacket Trucker Jacket

1. Denim Button-Up Shirt in Bluffton Wash | 2. Chambray Button-Up Workshirt | 3. Denim Big Shirt | 4. Relaxed Boyfriend Western Shirt | 5. Slim-fit chambray shirt | 6. Urban Renewal Vintage Oversized Chambray Button-Down Shirt

For some great duck boots and other waterproof shoes, I talked about my current favorites here.

The Chore Coat + Stripe combo

Chore Jacket | Jeans | Beanie | Boots (similar)| Bag

This chore coat is excellent – stiff cut (which is what you want), but soft and easy to layer. I have a couple vintage versions of these which I love but they are wider (likely because they were mens) and this is just a very slimming cut (if you are into that). Again over the same Target shirt, vintage Levi’s rolled up and old boots that tuck. But of course, I wanted a bit of a pattern so I added that beanie (Urban) and crossbody bag (similar).

The “If I Were To Wear Heels Again” Look

Turtleneck | Jacket (similar) | Jeans | Heels (similar)

I haven’t dabbled too much back into heels, but these (from & Other Stories three years ago) are still pretty darn comfortable because they are platforms. So I put them under my flares (Paige denim, last year) with the same Kule turtleneck, and my favorite tweed jacket (going on 6 years – WOAH). I feel like I could and will wear this to non-shopping meetings this fall to show that I can indeed look/feel pulled together but still casual.

1. Austina Coat | 2. Longline Plaid Blazer | 3. Scott Coat | 4. Women’s Plaid Coat | 5. Brushed Plaid Coat | 6. Plaid Double Breasted Overcoat

Ok, that’s it! What is everyone else wearing these days? Happy fall y’all 🙂

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2 years ago

I am very happy to see rugby shirts are back. They were my first experience in feeling fashionable as a younger kid.
You are nailing the Portland style, emily.

2 years ago
Reply to  Karen

I LOVE rugby shirts too!! so, much.

Rebecca Goodwin
2 years ago

Oh man those Loeffler Randall boots are to die! 😍 Definitely adding a brown lug sole boot to my fall shopping list.
Striped long sleeve tees have long been a fall staple for me too. They legit look good layered under everything and are so much more fun than a plain solid.
Excited to dress for fall now Emily, thanks for this! 😊

2 years ago

Most of this is very much not for me, but I love watching your style evolve in your new location. Keep the posts coming, it expands my mind to new style possibilities I wouldn’t have considered!

2 years ago

Although I live in a completely different part of the country (Nashville), I am loving these looks. In fact, this may have been your most relatable fashion post for me. I never knew I dressed like a grandpa from Portland, but I am into it!

2 years ago

I am into ALL of this. I am not feeling most of 2021 fashion (crop tops and stuff are just not a thing I’m ever going to enjoy) but fisherman vibes and dressed up sweats I can jam with. I’m still likely to just wear athleisure on the daily, but I love having a couple staples (like that Levi’s jacket!!) to lean on when something forces me out of my yoga pants.

2 years ago
Reply to  Theresa

OMGGGGG. I moved to Portland last year and I’m dying laughing at this. “From my office, I can see Canada and California at the same time.”

2 years ago
Reply to  Theresa

Thx, that is so funny.

2 years ago
Reply to  Theresa

I’m a lifelong Portlander, and I laughed so hard I cried at this. It was amazing.

2 years ago
Reply to  Theresa

 “I run home to change into my sexiest North Face rain-slicking shift dress, dress beanie, and high-heeled Timberland boots.”

2 years ago
Reply to  Theresa

So good! I live in Hobart, Tasmania, and I think this is what mainland Australians think we are up to down here!

2 years ago
Reply to  Alix

Indeed, we do! LOL 🤣
I’m in Perth.

2 years ago

The link to Emily’s jumpsuit is not the same one – please fix if able because I’d really like the one that she’s wearing. Thanks!

2 years ago

You are adorable. I love all of your style posts but this is my favorite because it’s so obviously stuff that you just love because you love it with no whiff of “fashion influencer “. Please keep them coming. And damn! There’s such a thing as a sweatshirt onesie and donesie?? WHERE HAS THAT BEEN ALL MY LIFE????

2 years ago

I love (almost) all of those outfits!!! It seems the link to the chore coat is not correct. Could you please fix it? Thank you!!!

2 years ago
Reply to  stinglhamber

I had the same frustration–that chore coat is practically perfect, but looks nothing like the one linked here. Anyway I’ve been crawling around the Alex Mill site and think it might be this one, but I’m not sure of it.

2 years ago

love these looks…..but you are missing a few key nw elements. never underestimate a pair of closed back clogs as a NW version of high heels that are pretty darn waterproof. gauze scarfs for the book end seasons are a must, too. other than that you have it nailed more or less. I did chuckle at many. especially the sloppy hipster. its the perfect school drop off outfit that may or may not be part pajamas.

Lynn W
2 years ago

Super cute!! A couple of these styles I could pull off here in AZ even….supposed to be on the 70’s this coming week. Lol. Love the Northwest vibe 🧡

Joan Renee Stark
2 years ago

Couldn’t all these “outfits” have been put together from thrift store clothes at a fraction of the price?

2 years ago

Love this post Emily! Living in the “other Portland” – (or the “original Portland” as we say here…:) this style completely resonates with ours here. Coveting the Loeffler boots but couldn’t quite spring for them, I found a similar Sorel pair and purchased the Alex Mill jacket. What I love (besides the Cobalt color), is that it gives me a little break from the denim jackets that I typically sport, while retaining the casual element and comfy material. I wear the jacket with my lined Carhartt leggings (for a look with tall boots) and black crop jeans to wear with my clogs (Danskos rule here in Maine!). I started following your fashion style a long time ago – please feel free to do more of these posts (especially now that you’re out of L/A :).

2 years ago

Wow – I’m inspired by every outfit! Love them all!

2 years ago

Emily it’s really fun seeing your new location inform your current style. I love “location drag” when I travel and it feels like you’re definitely leaning into Portland drag. I am HERE FOR IT.
I really like the vibe you have going and your eye is still top notch, just a bit more relatable because a lot of this stuff can be done affordably or second hand. Love it!

2 years ago

My favorite bits about this post were 1. The rando tennis shoe in the Denim on Denim post, because I like seeing people keeping it real, and 2. That Emily had multiple people tell her her outfit choices were not their cup of tea, and she just. Didn’t. Care. At All!!

2 years ago

I LOVE that you’re wearing what YOU LOVE and not giving a toss about so-called fashion = not a victim! Yaaay!
It’s a bit 70s grunge me thinks…comfy as, cozy and cool.

2 years ago

I love the updated style! Just wanted to pass along that recently new to me clothing store in Portland called Bridge & Burn has become my new go to. I think they aesthetic would mix well with yours. Really enjoying following along as your family adapts to Oregon!