OKAY FRIENDS. 

You are in for a wild blazer themed ride today–you asked, so you shall receive: 9 different ways to style your favorite blazer! ?

The plaid blazer, in particular, is one of my favorite staples for fall and winter. It’s classic and trendy at the same–you can dress it up, dress it down, wear it to the office, wear it on Saturday night–it’s one of the most versatile items you can buy, so if you’ve been looking for ways different to wear it, you are in the right place. ??

Let’s jump in, yes!? 

How to style a plaid blazer: 

Here, I’ll be styling Everlane’s oversized plaid blazer–you saw it first (and a couple of the outfits featured here) in my last Everlane capsule wardrobe! This cute version from Loft is also really similar and comes in petite, plus, and tall! This version from Old Navy is also super similar for only $45! 

Fit: The Everlane blazer I’m styling has an oversized fit (I’m wearing a 0–which is the size I wear in looser-fitting blazers, but not tight fitting blazers–I usually wear a 2 in those because I have broad shoulders.) If you’re in between sizes, I’d probably go with the smaller size. 

This blazer became an instant bestseller the first time I featured it, for very good reason–it’s a damn good wardrobe staple! It also comes in different colors if this grey subtle plaid isn’t your jam.

Before we get into how to style it, let’s back up and talk about the major kinds of blazers out there right now. 

Different plaid blazer styles: 

First, I thought it was important to cover a couple different styles of blazers here, because I often get questions on “which one is better”–the answer is–there is no right answer. It’s all about what you are drawn to! Here are some basics: 

Single-breasted: 

Okay, so blazers are typically single-breasted or double-breasted. I don’t think there is a right or wrong style to choose here–single-breasted just means there is ONE set of buttons. Again, the blazer I’m styling in this post is Everlane’s oversized single-breasted blazer. 

Double-breasted:

In contrast, a double-breasted blazer is a blazer with TWO sets of buttons–a set on each side. For example–this double-breasted blazer that Everlane just came out with. (I’m IN LOVE–don’t worry, I’m ordering it so I will do a follow-up styling session with that blazer!) 

And then there are the following subcategories. You can have a single-breasted or double-breasted blazer in either category: 

Classic tailored: 

If you like a more classic/preppy look, you may want to go with a more tailored blazer, which tends to hit close to the hip and is more form-fitting. You’ll see an example of that kind of blazer in this post. J.Crew’s Regent Blazer, for example, is an excellent well-known blazer I would define as “classic tailored.” 

Boyfriend/Oversized blazer:

Then we have a boyfriend blazer, which is what I’ll be styling here today! This is traditionally longer and looser in cut, and definitely more “trendy” vs. a fitted blazer. I would say a boyfriend blazer is more versatile with the ability to go from casual to dressy, day to night, whereas a classic blazer would look stuffy and out of place at say, a dive bar or on a date–a boyfriend blazer, on the other hand, paired with the right accessories would look right at home. It’s not so trendy though as to say that it will be out of style next season–you will definitely get a lot of wear out of this for years to come! 

Shop more favorite plaid blazers: 

What to wear with a plaid blazer? Here are nine plaid blazer outfits to copy this season!

1. With a white crewneck tee + mini skirt + ankle boots: 

Cotton crewneck tee (TTS, wearing small),Oversized Plaid Blazer (Oversized fit, wearing 0), Corduroy Skirt (runs TTS–wearing 0) ,Re-Knit Boot

I would wear this outfit pretty much anywhere! This outfit really represents two of my go-to blazer combos in one: 1. A plaid blazer + a mini skirt and/or 2. A plaid blazer and a white tee! Both foolproof outfit combos!

I especially love that the skirt is short but not TOO short, so you can wear it day or night. This is a great example of my Juxtaposition trick–AKA the foolproof method to building an interesting outfit!

Also, these booties make EVERYTHING look stylish and sophisticated. They’re the most comfortable booties ever–super stretchy (so they’re easy to get on over your ankle) and the heel is low and chunky, so you can walk forever in them! My favorite part is how they fit snug and high on the ankle for an unbeatably chic look. 

2. With a white tee + jeans + pumps: 

Cotton crewneck tee (TTS, wearing small), Cheeky Straight Jean, Oversized Plaid Blazer, Editor Heel 

Same tee, same blazer, TOTALLY different feel, right!? 

A simple crewneck tee + a classic jean + black pumps = one of favorite outfit combinations any time of the year. It’s timeless, it’s classic, it’s polished, and the shoes even make it a little bit sexy–add a blazer though, and it brings it to a whole different level! I would wear this anywhere from the office (I would’ve worn this to a client meeting when I worked in advertising!) to a date night. 

3. With a mini skirt + ankle boots: 

Washable Silk Blouse (TTS, wearing size 2),Corduroy Skirt (TTS, wearing 0), Oversized Plaid Blazer (Runs oversized, wearing 0), Corduroy Skirt (TTS), Re-Knit Boot (TTS)

I love this silk blouse so much I got it in two colors (the other one is the off-white!) It’s SILK and WASHABLE! (Two words that don’t often go together!) And if you’ve had a hard time dealing with silk shirts that are too sheer, you’re in luck, because these aren’t remotely see through! They are fantastic tops for layering under your favorite blazer! 

Here I paired it with Everlane’s adorable corduroy mini, which is a great seasonal twist on a summery white mini–plus their incredible knit sock booties, which are SO comfortable and chic looking! Can’t recommend them enough! This outfit is a great one that you can easily transition from day to night, too! (It would also look so cute with sneakers!) 

4. With black jeans + sneakers: 

Oversized Plaid Blazer, Similar striped tee, Everlane Modern Stretch Cigarette Ankle jeans(wearing my normal size–but if you’re in between, you may want to go up a size unless you want them super tight!) Tretorn Sneakers (run TTS) 

I love a blazer paired with jeans and sneakers! It’s the perfect high-low mix! We all know (as referenced above obvi) that a blazer and a tee are a match made in heaven–but a PLAID blazer paired with a STRIPED tee is real magic (mixing patterns always for the win! ??)

Pattern mixing tip: Alternate patterns of different scales and levels of business. This works because the plaid pattern is much bigger and more subtle, and the stripes are smaller/busier/bolder! 

Let’s also talk about these jeans for a second. They are BEST jeans that are a true black–they can easily be dressed up for work, and they hug every curve like a glove! They basically fit just like a skinny jean except for right at the end, when the leg stays straight instead of tapering in, so just like I say with the Cheeky jeans (below) they’re a great “starter jean” for someone trying to break out of the skinny jean rut! 

5. With an autumn pop of color + ankle boots: 

Waffle Knit Henley (TTS), Cheeky Straight Jean (runs TTS, wearing 25), Oversized Plaid Blazer, Re-Knit Boot (TTS) Old scarf

Want to be comfy and casual but still professional? Try this outfit combo! This would work great with any tee, not just a long sleeve henley, but I love how this one adds a pop of color!

These jeans and booties are made for each other–why? Because the jeans are the perfect cut (a straighter fit through the calf + cropped) and the booties are snug and cut a bit higher–above the ankle, so they still give you a pretty ankle line while–ding ding ding, KEEPING YOUR ANKLES WARM!! (Big bonus when it gets super cold out!) I also love the wash–it’s called the “indigo” wash–not TOO light blue, not too dark! 

I always say their Cheeky Straight jeans are great “starter jeans” when you’re looking to branch out from the classic skinny jeans without going too overly trendy with a mom jean or wide leg jean! 

On another note, a little neck scarf is the perfect accessory for a blazer–it adds a little extra dose of femininity while being super polished and chic! (See how to tie a short neck scarf here, and how to tie a longer neck scarf here!) 

6. With a graphic tee + mini skirt + OTK boots: 

Oversized Plaid Blazer, Femme Next Door Tee (my friend Juley’s company! She’ll be putting them up for sale soon, so stay tuned!) but in the meantime, I love J.Crew’s and Sezane’s graphic tees! Topshop green croc mini skirt (runs small–wish I’d sized up to a 4!) Stewart Weitzman Lowland boots–also available at Shopbop–run TTS! (Blondo makes my other OTK fave–budget-friendly and waterproof!)

Another blazer, mini skirt and tee combination–but a completely different look than the one above, am I right? This one is definitely more on-trend with a little bit of edge! It’s a great outfit that can really be worn anywhere from brunch with the girls to drinks on Saturday night. (It would also look adorable with sneakers or loafers, too!) 

7. With a graphic tee + crops + cap toe pumps: 

Oversized Plaid Blazer, Everlane Straight Leg Crops(TTS–wearing 0),Femme Next Door Tee (my friend Juley’s company! She’ll be putting them up for sale soon, so stay tuned!) but in the meantime, I love J.Crew’s and Sezane’s graphic tees! Sam Edelman Cap Toe Pumps (run big, go 1/2 size down!) 

Same tee, same blazer–but HOW different are these two outfits!?

These straight-leg crops from Everlane have definitely won the “most worn pair of pants” award over the past month or so. Boyfriend jeans or straight-leg jeans could easily be swapped in for this look as well, but I think these pants, in particular, elevate the outfit a bit and make it look a lot nicer–something you could totally wear to work or even a daytime date. I love the head to toe neutral with the blazer being the pop of subtle pattern that really brings it all together! 

8. Warm + Stylish for the office: 

Oversized Plaid Blazer, White button down (this one is a J.Crew Men’s small so it’s oversized!) Halogen cropped pants (size 0, run TTS!) Everlane Day Tote, Nordstrom booties (TTS–these are last year’s style so there are a few sizes left, but this year’s fully stocked version is nearly identical!) 

I definitely wanted to include one cold-weather work outfit in here, and I can’t recommend everything in this look enough! First, the blazer is obviously a staple to wear to the office, and if you want to spice things up, pair it with some fashion-forward cropped work pants, like this pair from Halogen! (This pair from J.Crew is super similar as well!) 

I often get asked “how do I wear cropped pants in the winter without freezing my ankles?!” and the answer is SOCK BOOTIES! The Everlane version I’m wearing above would also work great here, but I also love Vagabond sock booties from Nordstrom if you’re wanting something a little edgier! 

9. With black leather leggings and a white button-down: 

Oversized Plaid Blazer, White button down (this one is a J.Crew Men’s small so it’s oversized!) Spanx Leggings (I wear Small, size up if you’re in between!) Gucci Brixton Loafers (Sam Edelman makes my fave budget-friendly dupe!), Camel Beret 

Last, but not least–I had to include at least one outfit with leather leggings, yes? ?I LIVE in these during the winter, and I especially love them with an oversized white button-down! (Same one I’m wearing in the outfit above!) It’s crazy how differently you can style two classic items, right? Here, I’ve just swapped up the pants and shoes, and added a beret! It’s a combination that is classic, with a fashion-forward twist! 

Next time you reach for your plaid blazer, I hope this post serves as some inspiration! Happy outfit mixing! ??

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