Transition Your Favorite Dress Into Fall With These Smart Jacket Pairings

Fall has always been one of my favorite seasons, not just because fall fashion trends never fail to surprise, but the season’s brisk change in weather requires some creativity with your closet. After all, it’s no easy feat to get dressed for days that fluctuate dramatically in temperatures which is why it’s essential to have outfit formulas that are fall-friendly. One fail-proof recipe? Jackets with dresses. 


Not only does layering allow you to break out your jackets for fall, but if you haven’t had the chance to wear your favorite dress before the end of this summer, now is your chance. Ahead, we’ve rounded up the three best jacket styles to wear with dresses for fall. Keep reading for twenty-seven different ways to style your favorite dress this fall with key jackets.

Trench 

WHO: Ruva Takawira 

WHAT: COS Cotton Oversized Trench ($250); Rixo Phoebe Midi Dress ($215); Dr. Marten Jadon Boots ($180). 

WEAR: Trench coat + midi dress + combat boots.  

The greatest thing about investing in a trench coat for fall is that you can also pair it with all of the dresses you haven’t gotten to wear as much this summer (including that midi-dress). Whether you opt for a sweater midi-dress like Ruva or pair your trench with a lighter-weight dress, you can rest assured that this is a look that will garner many compliments. 

This coat would look so good with this Rixo crochet-knit midi dress ($455). 

WHO: Grece Ghanem 

WHAT: Bottega Veneta Shoulder Bag ($2,800).

WEAR: Trench coat, halter dress, zebra mules. 

It’s an understatement to say summer 2020 has been unlike any other, so if you find yourself in a fashion rut, we suggest is slipping into your favorite halter dress, with a matching trench coat and a statement shoe. Not only will you look chic like Grece Ghanem, but dressing up (even if there’s no occasion) can be fun, we promise.

Already have the statement shoes? We recommend this red Saint Genies trench coat ($90).

WHO: Izzy Lou 

WHAT: Zara Trench Coat, Oversized Poplin Shirt ($40), and Low Heel Rubber Boots ($80).

WEAR: Trench coat + oversized button-up + rainboots. 

Adding a jacket to any dress can immediately polish any look. Case in point, this outfit from Izzy Lou. Throwing on your oversized button-up dress with a trench and your rainboots is an effortless way to look chic this fall as it’s basically the embodiment of Cottagecore, just made for the outdoors.

Are you looking for a more affordable version? Try Topshop’s Trench Coat ($95).

WHO: Michelle Rose 

WHAT: With Jéan Andy Dress; Zara Denim Shoulder Bag ($20). 

WEAR: Trench coat + button-up dress + shoulder bag. 

The button-up dress you bought this summer is still fall-ready. Just pair it with a trench coat and a little shoulder bag for the chicest low-key look.

Still in search of the perfect button-up dress? We love this one from Uniqlo ($20).

WHO: Oumayma Elboumeshouli 

WHAT: Cekette Trench Coat With Pleated Back ($493); Marni Knitted Long Dress ($1590).

WEAR: Re-worked trench + Crewneck knit dress + knee-high boots. 

F/W 2020’s runways were filled with trench coats with reworked details like pleats, two-tones, cutouts, and even deconstructed hems—a trend we love. After all, who wouldn’t want to embrace unique jackets by pairing them with your go-to dress? Just try to deny your craving to cop this look from Oumayma Elboumeshouli.

On a budget? This two-tone trench from ASOS ($86) is a similar vibe.

WHO: Justyna Czerniak

WHAT: Dorothee Schumacher Trench ($1,288); One Shirt Button-Up; Munthe Dress; Bottega Veneta Shoulder Bag ($2,800). 

WEAR: Trench coat + printed puff sleeve dress + button up + knee-high boots. 

When discussing essential jackets, it doesn’t get better than a classic trench. Not only are they timeless, but they can meld well with trends of the moment. Don’t believe us? Look to Justyna Czerniak’s look for proof that you can mix the poppin’ things of the moment—like puff-sleeved dresses—with timeless pieces for a look as crisp as the fall air.

Love this look but wish that the dress was black? We got you. Try this black puff-sleeve &OtherStories dress ($44).

WHO: Karina Mariott 

WHAT: River Island Trench Coat and Dress; Topshop mules. 

WEAR: Nude trench coat + printed body con dress + mules. 

Not sold yet on the idea of throwing your trench jacket over your dress? Let Karina’s bodycon dress outfit be a reminder that this look is as timeless as ever. While she wore this look pre-COVID, it’s a look that’s still fresh today.

Not in your size? We recommend this similar Wednesday Girl Vinyl Trench Coat ($76).

WHO: Naomi Ross 

WHAT: H&M Trench; Leol The Label Satin Midi Dress ($180); Zara Boots. 

WEAR: Printed trench + satin button-up dress + combat boots. 

If the classic khaki trench isn’t your style, then we recommend taking a cue from Naomi Ross and pairing a printed trench coat with a silk dress and combat boots for fall. (Pro tip: keep the colors in the same palette to make it look extra-expensive).

Can’t splurge atm? Here’s a cheaper satin dress alternative from ASOS ($183).

WHO: Charlotte 

WHAT: Nelly sweater dress. 

WEAR: Trench coat + Sweater Dress +  Chelsea Boots. 

Pairing a jacket with a dress isn’t just a look you can wear during the fall; you can wear it well into the winter too. Just opt for a chunky full-length sweater dress like Charlotte and pair it with your trench and Chelsea boots for a cozy look.

We also love this turtleneck sweater dress from Nanushka ($370).

Blazer

WHO: Div Ravindran 

WHAT: Arket Leather blazer; Balenciaga Oversized T-shirt; Zara boots. 

WEAR: Leather blazer + over-sized t-shirt dress + Chelsea boots.  

Blazers are another jacket style that you should definitely lean-on this season as suiting will continue to dominate your feeds. One style we’re placing bets on for fall? Leather, as seen here on Div Ravindran.

 

Looking for a similar Balenciaga oversized t-shirt? Try this one ($615).

WHO: Paulina Joaristi

WHAT: Amazon blazer and dress; Schutz Julyanne Boot ($298); Dior saddlebag. 

WEAR: Black blazer, black mini turtleneck, knee-high chocolate brown boots. 

Not sure where to start when it comes to styling your blazer? Don’t overthink it. Try replicating Paulina Joaristi’s stunning-yet-straightforward outfit and pair your go-to black blazer with a turtleneck dress. Finish off the look with chocolate brown accessories, and you’ve got a fall-ready look that’s bound to turn heads.

Re-create this look for yourself…
Schutz Diasy Boots

Want to replace your trusty blazer? We recommend this affordable version from Lark & Ro ($50).

WHO: Kylee Walker 

WHAT: Vintage leather blazer; Aritzia Neon Dress. 

WEAR: Chocolate brown blazer + neon mini tank dress.  

If you love the idea of embracing fall’s most significant color trend but can’t figure out how to pair brown and black, we recommend looking to Kylee Walker for inspiration. When deciding what jacket to wear with a dress this fall, don’t be afraid to experiment with colors and pair neons with nudes. In the end, you’ll get not only to wear the trendiest colors but also to create a look like no other. 

 

WHO: Nina Sandbech

WHAT: Lesyanebo Blazer; Olivia Rubin Ombre Satin Dress ($400)

WEAR: Colorful blazer + slip dress + clutch bag 

Live for color? Then this jacket and dress outfit idea from Nina Sandbech is right up your alley. Just pair a colorful blazer with an ombré dress, and you’ll be wearing the rainbow—bonus points for adding a bright clutch bag.

Need a great clutch? We love this Mansur Gavriel Cloud Clutch ($495).

WHO: Jeannine Roxas 

WHAT: Princess Polly mini satin dress; Dr. Marten Shriver Hi Boots ($160); Lès Amis sunglasses ($35); Nakd Fashion shoulder bag. 

WEAR:  Blazer + mini slip dress + combat boots.

Let’s be real: one of the most challenging parts of getting dressed in fall is deciding between wearing the dress you loved all summer or busting out your new boots. Luckily we don’t have to choose. You can wear your favorite mini dress and new combat boots, just don’t forget to throw on a blazer to finish the look.

Re-create this look for yourself…
H&M Oversized Jacket

Pair this blazer with these Dr. Marten Boots ($160).

WHO: Franny Fyne 

WHAT: Vintage blazer and dress; Faguo sneakers.  

WEAR: Blazer + printed button-up dress + sneakers. 

You don’t necessarily have to buy new things for fall—just look to Franny Fyne’s outfit as proof. Whether you already own a pretty printed button-up dress, or you shop one-second hand, pairing a vintage blazer with a printed dress and sneakers is the smartest look to try for your wallet, the weather, and the planet.

Prefer second-hand pieces? Try shopping from the Black-owned vintage commerce site, Thrilling.

WHO: Caroline Lin

WHAT: Vintage blazer; Ralph Lauren Shoulder Bag; Prada Sunglasses. 

WEAR: Oversized blazer, button-up dress, knee-high boots. 

A reminder that vintage pieces don’t mean dated looks. Proof lies in this jacket and dress ensemble from Caroline Lin. This classic oversized blazer paired with a button-up dress and boots is not only fresher than ever, but it’s easy to replicate no matter your budget or where you find the pieces.

 

We also love this unique two-tone blazer from Tibi ($795).

WHO: Caroline

WHAT: H&M Blazer; Zara Shoulder bag; Nasty Gal boots.

WEAR: Black leather blazer, over-sized t-shirt, white knee-high boots. 

Not to sound like a broken record here, but leather blazers are very-much are a trend we’re riding with since it’s a jacket that can be styled with just about any type of dress. But if you’re still unsure about this look, we recommend pairing it with an oversized t-shirt dress and matching boots (like Caroline). We promise you’ll love it.

Pair these boots with Altaire’s baguette box ($455).

WHO: Rianna Mara

WHAT: H&M Blazer, and slides; Zara dress. 

WEAR: Nude blazer + gray tank dress + slides. 

Blazers are the jacket that reigns supreme: you can wear them with just about anything, anywhere, and anyone can pull them off. But if you’re looking for a casual blazer and dress pairing, look to Rianna Mara’s look for inspiration. Throw on your tank dress, a lightweight blazer, and your slides for a day or errands or relaxing. No matter what you do, you can’t go wrong with a blazer and your favorite everyday dress.

Need a cozy slide? You may like Nomasei’s mule ($160).

Leather Jacket

WHO: Naomi Paris 

WHAT: Nasty Gal Croc Trench; Mango Slip Dress; Telfar Shopping Bag ($257), Nike Air Force 1 Sneakers ($90). 

WEAR: Faux animal leather jacket + sheer turtleneck + slip dress + sneakers. 

Layering is the key to nailing any fall look, and there’s no better way to embrace the outfit formula  than pairing a leather trench jacket with your favorite slip dress. To take this look to the next-level look to Naomi Paris for inspiration, and layer a sheer turtleneck under your slip dress, and opt for either a faux croc or snake trench with your sneakers.

Need a new pair of sneakers? We recommend these classic white Puma sneakers ($60).

WHO: Brittany Mercer 

WHAT: Leith Long Sleeve Body-Con Dress. 

WEAR: Leather motorcycle jacket + animal print dress + over-the-knee boots. 

Not a fan of full-length leather trench coats, but still want to incorporate animal print into your fall wardrobe? Look to Brittany Mercer for inspiration. Pair your classic leather motorcycle jacket with a snake print dress and over-the-knee boots this fall.

Are you searching for an animal print dress? Try Good American’s Leopard Slip Dress ($105).

WHO: Huma Karim 

WHAT: Zara motorcycle jacket, slip dress, and boots. 

WEAR: Leather motorcycle jacket, slip dress, cowboy boots. 

If animal print isn’t your thing but you still want your motorcycle jacket to be your fall wardrobe hero? Look to Huma Karim’s chic but straightforward outfit as your guiding light and pair your jacket with a slip dress and cowboy boots.

We also love this budget-friendly Dolce Vita Boot ($160).

WHO: Maria Macfarlane

WHAT: Topshop Jacket and Boots; Joanie dress. 

WEAR Colorful leather jacket + polka dot dress + pointed ankle boots. 

Leather jackets don’t have to be limited to neutral tones. In fact, we encourage you to embrace a little color this fall when it comes to your coats. Just make sure you pick a color you love, and like Maria Mafarlane, pair your jacket with a dress and boots in the same color wheel to pull off the statement look with ease.

We recommend pairing this jacket with Afrm’s polka dot dress ($90).

WHO: Marylin. 

WHAT: H&M Trench Coat; Zara Shoes. 

WEAR: Black leather trench coat + Black turtleneck dress + white shoes. 

Not a fan of colorful leather trenches? Let Marylin’s outfit serve as a reminder that you don’t have to opt for color (if it’s not your thing) to be able to pair this iconic jacket style with a dress. You can keep it neutral, and let the coat do all the talking, or pair the piece with a different colored shoe for a pop.

Want a black leather trench? Let us introduce you to this one from Apparis ($380).

WHO: Grace-Caroline Larcade 

WHAT: Zara motorcycle jacket; Les Petits Joueurs Buckle bag ($640); Rixo dress. 

WEAR: Leather motorcycle jacket + colorful maxi dress + mules. 

Still not sold on leather blazers? That’s ok, just hang on to that old motorcycle jacket for fall. But if you’re looking for a fresh way to style your jacket, we recommend copying Grace-Caroline Larcade and pairing it with a colorful maxi dress (of any kind) and mules. It’s a fail-proof look for fall, trust us.

Pair this dress with these stunning Chelsea Paris mules ($325).

WHO: Hanna Stefansson 

WHAT: Remain Birger Christensen Coat; Byfar Yellow Patent Bag ($504).

WEAR: Colorful leather trench + retro print button-up mini dress + flat knee-high boots + shoulder bag. 

The best jackets to wear with dresses accentuate your personality, which is why we recommend taking a cue from Hanna Stefansson and getting bold with your pairings. Consider this your free-pass to ditch the rules and mix up the pieces you love the most. Having fun with it is all that matters.

This coat would look fire with this Dodo Bar Or floral print dress ($760).

WHO: Jasmine Fox-Suliaman 

WHAT: I.Am.Gia Anastasia Trench ($100); Wilfred Only Slip Dress ($118); Dr. Marten Jadon Boot ($180); Staud Alice Bag ($139); Argentino Vivo Necklace ($88). 

WEAR: Full-length leather duster + slip dress + chains + platform boots. 

Yes, if you’ve made it this far, you’ve realized there are a few repeat pieces—but that’s the point. The smartest (and most stylish pieces might we add) can be worn in various ways (ahem, like full-length leather jackets and slip dresses). These staple pieces are far from overdone. All you have to do is style them your way with your favorite boots for a winning outfit combo that even an editor would wear.

Already have your go-to black slip dress? Let’s talk about this zodiac-embroidered slip from Realisation Par ($250).

WHO: Tyla-Lauren 

WHAT: Who What Wear Leather Trench Dress; Lack of Color Hat; Public Desire Boots. 

WEAR: Leather trench dress + cowboy boots + fedora. 

Ok, so it may seem counterintuitive at this point, but if you’re still not sure what jacket to wear with your dresses for fall, may we suggest something mind-blowing? Wear your leather trench as a dress. No matter if you choose to wear a jacket that doubles as a dress or pair your jacket with your favorite dress, there are so many ways to utilize the items that are already in your closet. All it takes is a little ingenuity and some great staple pieces.

We recommend pairing this dress with these Off-White boots ($1,193).

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