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The Comfiest Linen Shorts + 6 Ways to Wear Them From Summer to Fall

Aug 26, 2020

Alright, so remember our #RealTalk on the below Instagram post a couple weeks back? About how it is VERY perfectly normal (and to be expected!) if our clothes aren’t fitting us the way they used to? Well today’s post is kind of a continuation of that! 

Because none of my existing shorts or pants were fitting me in a way that was comfortable (they were all too small!) I decided to buy two new pairs of roomy linen shorts over the past month or so, and it was such a good decision. I have always been a proponent of wearing the clothes that fit your body RIGHT NOW–not trying to fit your body into your clothes! Wearing clothes that make me comfortable AND that are cute and versatile are a must! If you have the means, buying a couple new pieces that fit you AND make you look forward to getting dressed at this very moment is going to make a world of difference! 

Enter: The linen shorts. I first got this pair called “The Seaside Shorts” from J.Crew and was wearing them so much that I needed another pair to throw into the rotation, so I ordered this similar pair from Nordstrom because I adored this burnt orange color! (Although they come in olive, black, and white too!)

Despite being part of the “extremely casual summer wear” category, I also wanted to show you that a pair of staple linen shorts can be a lot more versatile than you might think! Today, I’m sharing 6 outfits to wear them with, from summer to early fall, whether you’re wearing them out to the park or patio or staying home–these are comfy enough to quite literally LIVE in!

Let’s go! 

6 Ways to wear Linen Shorts from Summer to Fall 

With espadrilles for an al fresco dinner date 

How to wear Linen Shorts from Summer to Fall 

Top: Everlane (got it several months back but if you prefer to shop elsewhere, J.Crew has many cute similar options–like this one–which is on sale for 35% off, and this eyelet version is SO cute and feminine!) Shorts: Leith, I have a small–they run a bit oversized! I also have J.Crew’s version and love those as well and sizing runs the same! Shoes: Soludos (I have this pair, but they come in different heel heights too! If I were buying them now in 2020 I’d probably go for the lower “Lyons” heel! The flats version are also so cute.) Earrings: Lace and Pearls (I also have this pair from her and adore them too! My friend Asa’s jewelry company!) Purse: Old but this one is cute and similar! 

Date night outfits might look a little different these days, but I would wear this comfy and chic outfit even BEFORE 2020! ???? This is a combination that would be perfect for a socially distanced dinner on your favorite patio–whether that’s a local restaurant’s (Osteria Rusticana for me!) or your own back yard! 

With a sweater tank and slides for a transitional look

How to wear Linen Shorts from Summer to Fall 

Sweater tank: J.Crew (on sale but going fast! Runs TTS–I’m wearing a small!) Shorts: Leith, I have a small–they run a bit oversized! I also have J.Crew’s version and love those as well and sizing runs the same! Shoes: Madewell mules (part of the Nordstrom sale! And still in stock!) Earrings: Lace and Pearls (I also have this pair from her and adore them too! My friend Asa’s jewelry company!) Jean jacket: J.Crew 

A sweater tank and these linen shorts are a summery match made in heaven! I actually wore this combo to dinner the other night–speaking of my favorite local Italian spot, Osteria Rusticana. ???? I was skeptical of the sweater tank, but turns out, I love it! It’s easier to dress up than a regular tank top, and makes any outfit way more interesting!

Because it’s summer I wore it with sandals, but for a more transitional look, these mules are perfect! I love the pop of print, and they are great “house shoes”–AKA–shoes that you can easily slip on and off, are comfortable, but count as “real clothes.” 

With a linen button-down and birks for the beach 

How to wear Linen Shorts from Summer to Fall 

Shorts: Leith, I have a small–they run a bit oversized! I also have J.Crew’s version and love those as well and sizing runs the same! Shoes: Birkenstocks (whole review on them here!) Linen button-up: Outerknown (my other summer must-have! I have another color that I wore in this post! Runs TTS–I have both a small and a medium and both work!) 

Okay okay you KNEW there was going to be at least one look featuring my other two Summer 2020 must-haves: this linen button down that I love so much AND the waterproof EVA Birkenstocks! I have been wearing iterations of this outfit everywhere from the beach, to camping, to working from home. (A very zoom-friendly outfit!)

Another perk of the Birkenstocks: these are great “wear at home” shoes because they’re very supportive–Neal has been struggling with plantar fascitiis and walking around barefoot wasn’t doing him any favors, so he got these (they come in mens sizes, too) and said they’ve been helping a lot. Of course, he also got them in white. So now we match. ????

With a matching sweatshirt for a faux romper look

How to wear Linen Shorts from Summer to Fall 

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How to wear Linen Shorts from Summer to Fall 

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Sweatshirt: Outerknown cropped sweatshirt Shorts: Leith, I have a small–they run a bit oversized! I also have J.Crew’s version and love those as well and sizing runs the same! Shoes: Tevas (run TTS!), Allbirds Wool Runners (also TS) 

Okay this faux matchy-matchy set just got me really jazzed so I went wild and styled it with not one but three pairs of shoes to show how versatile it is. Whether you’re lounging around, running to the grocery store, camping (with TEVAS, obvi ????), or working from home–there are so many ways to wear it that are so cute! I recently purchased this sweatshirt from Outerknown (a new-to-me sustainable brand I’ve fallen in love with recently!) for our upcoming Lake House trip. I love that it’s lightweight, terry on the inside, and it’s more of a feminine cut–a little bit cropped! They have so many pretty faded colors, too! 

With a cable-knit sweater for chilly nights

cable-knit sweater

Shorts: Leith, I have a small–they run a bit oversized! I also have J.Crew’s version and love those as well and sizing runs the same! Sweater: old, but similar here! If you want a TRULY classic Fisherman’s sweater, I love this LLBean one! Huarache sandals: Nisolo (there are also lots of great versions on Etsy!) 

You know those late summer/early fall nights where it’s warm during the day but crisp in the mornings and evenings? This is the perfect thing to wear! Throw on a classic cableknit sweater and some Huarache sandals–my favorite in the summer, but also the shoulder seasons–because they’re closed-toe, you’ll get more wear out of them when temperatures are a little cooler, too! I just love the way they look with everything! 

With a graphic tee and cozy cardigan to work from home

graphic tee and cozy cardigan

Shorts: Leith, I have a small–they run a bit oversized! I also have J.Crew’s version and love those as well and sizing runs the same! Windy City Tee: Alice & Wonder (runs TTS! I have a small) Cardigan: Nordstrom (only $39–part of the Nordstrom sale and it’s my #1 pick AND still in stock! Runs TTS!) 

The perfect work from home outfit–comfy, but DRESSED in real clothes! The best of both worlds! I have really started getting into fun graphic tees even more since quarantine–they always make you smile when you put them on! Also, thislong, cozy cardigan is my #1 pick from the Nordstrom sale and it’s still in stock! Comes in so many colors, is SO soft, and looks way more expensive than it is–it’s basically like a bathrobe, but real clothes! ???? 

That’s all for now! Thank you for coming to my linen shorts Ted Talk and have a fantastic Wednesday! 

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