I'm not one to be overdramatic, but trust me when I say I reach for a pair of denim jeans nearly every day without fail. But while I will always love the classic jeans and a nice top combination, from blue jeans with a white tee to black jeans and a blazer, as well as everything in between, I also envy those who wear chic dresses come rain or shine. Admittedly, I normally save mini dresses for summer holidays, while midi and maxi dresses are my go-to for special occasions, such as weddings or christenings. However, I desperately want to change things up this season and embrace dress outfits more often, even in the colder months.
So, in a bid to shake up my fashion formula, I have been taking style inspiration from those in the know. Turns out, there are plenty of ways to wear dresses outside of the summer months and special occasions, and footwear plays a key part in that. The secret to wearing dresses in autumn and staying chic yet weather-appropriate is pairing them with boots.
From satin maxi dresses with knee-high boots for date night, to knitted dresses with chunky biker boots for cosy autumn/winter dressing, and an LBD with heeled ankle boots for any outing in between, there are plenty of dress-and-boot combos that work. Even mini dresses have a place in your wardrobe outside of the warmer months (you'll see how soon enough!).
So, without further ado, keep scrolling for the chicest dress-and-boot outfits to swap your jeans for this autumn. Enjoy!
6 Dress-and-Boot Outfits I'm Rotating:
1. Silk Dress + Knee-High Boots
Style Notes: For elegant evenings out or special occasions, a satin slip dress is a popular choice. But, if you are dressing for autumn/winter and you want footwear that is comfortable, chic and more protective than your open-toe stilettos (no shade) on a rainy day, then knee-high boots are a saving grace.
Shop the Look:
This satin maxi dress with a halterneck and strappy back detail is as elegant as they come.
These are such a fantastic pair of high-street boots!
No wardrobe is complete without a great blazer, end of.
These drop-down earrings tie the full monochromatic look together.
2. LBD + Heeled Ankle Boots
Style Notes: Whether you consider the LBD acronym to refer to a little black dress or long black dress, it's been a go-to staple for many decades. The best part about an LBD is how versatile it is; team with heeled ankle boots like Salome to take you from day to night, though you can pair it with ballet pumps, trainers or stilettos , too.
Shop the Look:
Such a pretty piece.
A heeled ankle boot is a failsafe wardrobe staple.
If you want an extra layer to keep the chill at bay, I would turn to a trusty leather jacket.
When styling a delicate dress, I love the contrast more hardy accessories offer.
3. Midi Dress + Chunky Boots
Style Notes: Emma proves that a midi dress styled with chunky biker boots and a suede jacket is an easy yet stylish look you can rely on when you don't have a clue what to wear. This is a particular combo I often reach for mid-way through autumn, when it's not cold enough for coats and knits but too chilly for sandals.
Shop the Look:
Pull out colours in the embroidered detail when accessorising to show off the craftsmanship of this ornate Doen dress.
The sell-out suede jacket is finally back in stock, but I doubt it will be for long.
These will never go out of style.
A vibrant cross-body bag will add a pop of colour to any look in an instant.
4. Knitted Dress + Biker Boots
Style Notes: Now autumn has arrived, I am desperately seeking out my cosy knitwear, and I don't just mean wool cardigans and jumpers, but knitted dresses, too. And, a knitted dress pairs perfectly with a pair of edgy biker boots à la Cristina.
Shop the Look:
So cosy.
Buckle biker boots have been a new addition to my boot collection in recent times.
Because the winter sun can be blinding, even if it is cold outside.
To finish the look!
5. Mini Dress + Knee-High Boots
Style Notes: I used to shy away from mini dresses outside of the summer months, but Liv has encouraged me to think otherwise with her preppy ensemble. The pinafore-style mini dress is a nod to the '60s and '70s, so pairing this dress with a pair of knee-high boots with a chunky heel is a match made in heaven.
Shop the Look:
So cute!
No autumn/winter wardrobe is complete without a turtleneck, and Uniqlo's Merino Ribbed Jumpers are my go-to because they are ultra soft, versatile and don't irritate my skin.
Yes, please!
I've been eyeing up these boots for a while now...
6. White Lace Dress + Western Boots
Style Notes: Chloe nails so many trends here with her suede jacket, boho-style white lace dress and Western boots, but all you really need to know is that white dress and black boot combo always looks chic. That's all!
Shop the Look:
I would also wear this with a chunky cashmere jumper and trainers.
These come in four different colours.
I've seen this in store and it's so chic.
-
From Engagement to Holiday Parties, My Closet Is in Need of Some Fancy Dresses—32 Chic Options I'm EyeingHere are the standouts.
-
Listen, Being Cool in 2025 Requires Just Two Things: Loose Jeans and This “Weird” Viral Flat-Shoe TrendThey're strange, but so chic.
-
These Easy Outfit Formulas Make Even Fall's Most Polarizing Boot Trend Look CoolSee the inspiration inside.
-
This Is the Luxe Fall Shoe Trend Every Fashion Person Is Already Wearing on RepeatCount these inspo pics as proof.
-
It's Controversial (I Know), But Frequent Fashion Flyers Swear By This Jeans Outfit for Long FlightsIt involves an elegant leather coat and chic luggage.
-
Taylor Swift Just Wore the Skirt-and-Boots Combo That Screams '90s Jennifer AnistonIt's foolproof.
-
I'm a Bridal Stylist—These Are the Best Fall Wedding Guest Dresses Under $500The couple is sure to approve.
-
A Rich-Looking Closet Is the Vibe—These 30 Amazon Picks Surprisingly Fit the BillSee the affordable yet chic finds.
