7 Fresh Ways Everyone Will Style Their Tailored Pieces This Fall

As soon as the first leaf hits the ground, I start contemplating who I’ll be stylistically in fall. This year, tailored pieces are calling my name—something you never would have caught me saying just a couple of years ago. I'm still a bit burned out from years of adhering to a mandatory business-casual dress code, so willingly choosing to wear tailored pieces is low-key shocking and definitely feels like a full-circle fashion moment for me.

So what changed, you might ask? Three things: 1) looser-fitting pieces, 2) the styling of them, and 3) there's something about mandatory dress codes that brings out my inner rebel (beyond the scope of this article). The surge in looser styles makes tailored pieces way more appealing to this cozy girl. Also, this fall, fashion people are styling their tailored pieces in fresh, surprising ways and bringing sexy back to tailoring in the process. So go ahead and open that drawer with all your Monday-though-Friday “work clothes” because we are about to start wearing them during primetime, baby.

Keep scrolling to get ahead of the trend, and see the seven outfit combinations you’ll want to replicate starting yesterday.

Pleated Pants + Corset Top

Tailored fall outfits 2021: pleated pant and corset top



Paloma Elsesser nails every look, and this one is no exception. Go for relaxed, pleated pants that sit at the natural hip to give the outfit an air of je ne sais quoi. This silhouette is part of a larger trend of pairing baggy bottoms with fitted tops, so we'll be seeing more of this combination into 2022.

I have these—they're the perfect shape and color.

This double-layered corset is a sight to behold. 

This upcycled corset top is sturdy and fits beautifully according to the reviews.

Trench Coat + Roomy Shorts + Knee-High Boots

First of all, we L.A. girls used to get roasted for the shorts-and-boots combination. Look at us now. The various elements of this outfit keep us ready for any weather, and what says fall more than that? 

This season, we are going for long trench coats and regulating our temperature underneath by combining roomy shorts and knee-high chunky boots. I have to say this outfit is one of my favorites. 

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I'm imagining this with a cute minidress underneath. This coat will be so helpful while you're en route to the party on the MTA.

Most people have to search vintage stores for years to find the perfect leather trench.

I'm betting big on boxers this season, too.

I'm obsessed with lug-heel boots, but most are too heavy to be practical. These are the perfect compromise.

Vest Matching Set

If you haven't heard, vests are the new wardrobe essential to add to your rotation this fall. Pretty much every brand has created a version, so you can take your pick of several different styles, from halter to cropped. Many vests are sold in a set with pleated pants, which makes dressing super easy. They also look great with skirts and jeans.

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This vest reads as a halter top.

I'm calling it: This is the top of the season.

To be paired with a heavy dose of romance.

Love the cropped cut of this vest. It would look great with low-rise, baggy jeans.

Wear this with no shirt and a voluminous skirt, if you dare.

Power Suit + Lace Top

Tailored fall outfits 2021: power suit and lace top



One of the recurring themes underpinning all of these looks is that they add a bit of levity to traditional tailoring. Dua Lipa's birthday look does a great job of this for a multitude of reasons, my favorite of which is the decision to wear a lace bra underneath her suit. It's unexpected, which we always love.

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Nothing says powerful like some strong shoulders.

Shop the matching Side Slit Pants ($120).

I always go for classic pieces that feature a unique detail. These puff sleeves look so elegant.

That feeling of accomplishment when you're showing just enough skin.

Mismatched Suit Separates

Welcome to the mismatched-suiting wave that we will all be surfing very shortly. If you're like me, you rarely buy a full suit and instead have a number of mismatched separates already in your wardrobe. Needless to say, this trend will be very easy to accomplish with what you already have. Stick to shades in the same color family to make sure the look is still seamless.

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This hue of blue will look so chic with all your blue jeans.

The textured pinstripe is intentionally imperfect, which is how I like it.

Pair different plaid and checker prints for a true fashion moment.

Don't these pinstripes resemble corduroy? More texture, real or imagined, is always a win.

Shorts Suit + Plain White Tee

Have you seen the TikTok trend where people try to dress "clean"? This is the look in a nutshell. The trick to getting the look is to build a wardrobe of timeless, simple basics that can be paired together in endless combinations with little to no thought. Take, for example, this tailored shorts suit paired with a plain white tee—you can't tell me she doesn't look clean, and I bet this outfit took her less than five minutes to assemble. I'm taking notes.

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C'mon—these are so chic! Pair them with a white tee and oxfords, and you're done.

Forgoing all my basketball shorts in lieu of these until further notice.

This chocolaty brown is so good.

Shop the matching Linen Shorts ($50).

Finally, a T-shirt made to be permanently tucked in.

Go for a crew-neck tee like this one from Zara.

Oversize Button-Down Worn as a Cardigan

Tailored fall outfits 2021: oversized button-down worn as a cardigan



The number of oversize button-downs (herein referred to as OBDs) in my closet has been steadily increasing, and I'm not mad at all. This fall, I plan on wearing them as cardigans over every outfit imaginable. Combinations I have already tried include scarf top + OBD, workout set + OBD, and pleated pants + sports bra + OBD. Raya's outfit is a perfect example of the versatility of this shirt—it really polishes off any look.

I have a feeling cuff links will become a thing for women very soon. For now, you can cop this shirt from the men's section.