21 Chic Travel Outfits for London in September (You Won’t Believe #7!)

Planning a trip to London in September? I’ve been there—and trust me, packing smart can make or break your experience.

The weather walks a fine line between late summer sunshine and early fall chills.

Here’s exactly what to wear in London in September so you can stay comfortable, stylish, and prepared for anything the city throws at you!

1. Classic Trench Coat with Chic Dress

A classic trench coat is a must-have in any London wardrobe, especially in September when the weather can be quite unpredictable.

Wear it over a chic midi dress, like the chic midi dress, available in flowy fabrics and autumnal colors like mustard or burgundy.

This combination is not only fashionable but functional; the trench protects against sudden rain showers while the dress keeps you comfy for a day of exploring.

For footwear, opt for stylish ankle boots that offer both comfort and elegance, making them perfect for navigating the city’s streets.

Pair these with a crossbody bag for practical elegance. You’ll look effortlessly put together while sipping your morning coffee at a quaint café.

When selecting your outerwear, consider the lightweight trench coat, which easily folds into your bag for convenience.

Layering with a light sweater underneath can add warmth if it gets chilly, and don’t shy away from patterns—stripes or florals can add a unique touch to your outfit.

A classic trench coat over a chic dress isn’t just fashion; it’s your secret weapon against London’s unpredictable September weather. Stay stylish and prepared for anything the city throws your way!

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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2. Layered Turtleneck and Jeans

Nothing screams smart-casual quite like a layered turtleneck paired with your favorite high-waisted jeans.

Opt for a lightweight turtleneck sweater in a neutral shade for a breathable and chic base layer.

To add sophistication, throw on a tailored blazer that elevates the overall look while still keeping it relaxed.

The jeans maintain a modern edge, perfect for exploring the city.

Finish the outfit with sleek loafers or stylish sneakers for all-day walking comfort. Don’t forget to consider denim in darker washes, which seamlessly tie in with the fall theme.

To further elevate your look, add a statement belt, and for that extra touch of style and warmth, wrap yourself in a stylish scarf that doubles as both a fashion accessory and a cozy layer.

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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3. Cozy Sweater with Pleated Skirt

A cozy sweater paired with a pleated skirt is perfect for the transition into fall.

Choose an oversized knit sweater in a rich autumn color like deep green or burnt orange, which not only keeps you warm but also looks chic.

The soft fabric will provide comfort during those brisk September strolls in London. The pleated skirt adds a touch of femininity and movement to your outfit, making it great for both daytime outings and evening dinners.

Opt for a midi pleated skirt to ensure versatility and trendiness.

For an elevated look that keeps you cozy, pair this ensemble with knee-high boots. Not only do they add style, but they also provide warmth as the temperature drops.

You can also consider layering with a denim jacket or a lightweight bomber for additional flair.

Dressing for London in September? Embrace the magic of cozy sweaters and pleated skirts! They offer warmth and effortless style, perfect for capturing autumn’s charm in every stroll and soirée.

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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4. Stylish Jumpsuit with Denim Jacket

A chic jumpsuit is a go-to outfit for any travel adventure, and in London, it shines with a denim jacket thrown over it.

For a stylish option, consider the chic jumpsuit, which comes in a bold color or print that stands out while being practical for all-day wear.

The denim jacket, like this denim jacket, serves as the perfect layer for cooler evenings and can be tied around your waist during the day for a fun, laid-back vibe.

To keep your look comfy yet trendy, pair your outfit with wedge sneakers or stylish flats. These options not only provide comfort for exploring the city, but they also elevate your outfit.

• Look for jumpsuits with pockets; they’re incredibly handy.
• A cinched waist adds definition to your silhouette.
• Accessories like hoop earrings or a delicate necklace can add just the right touch.

With this combination, you’ll be ready to take on London in style!

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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5. Long Cardigan with Graphic Tee

A long cardigan adds the perfect touch of coziness to any outfit. Layer it over a fun graphic tee and high-waisted trousers for a look that’s both comfy and stylish.

This ensemble works great for those chillier September days when you want to stay warm while enjoying the sights.

Opt for a light, neutral cardigan, like this oversized long cardigan, which provides added comfort and a relaxed vibe.

You can easily mix and match colors and patterns with your graphic tee to express your personality.

Complete your look with trendy ankle boots for an instant style upgrade. These ankle boots not only enhance your outfit but also ensure you’re ready for all the walking and exploration that London has to offer.

By choosing slightly oversized cardigans, you elevate your comfort while maintaining a chic appearance.

So, grab your crossbody bag for hands-free convenience and get ready to take on the city in style!

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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6. Flowy Maxi Dress with Western Boots

Transition into fall with a flowy maxi dress paired with western boots for a fun, bohemian vibe.

A flowy maxi dress in floral or earthy tones is perfect for layering, allowing you to easily add a denim jacket, like this denim jacket for a bit of edge.

Western boots, such as the western boots, not only keep your feet warm but also provide a trendy touch to your outfit.

This look is ideal for a stroll along the Thames or visiting some of London’s outdoor markets.

For an added bohemian flair, consider pairing with a wide-brimmed hat. As the weather cools, opt for dresses with longer sleeves, and don’t forget to accessorize with simple jewelry to keep it chic.

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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7. Tailored Blazer with Culottes

For a polished yet trendy look, consider a tailored blazer paired with culottes. This outfit is a fabulous choice for more formal outings or nice dinners in the city.

The culottes provide comfort while still looking chic, and a fitted blazer pulls the entire outfit together, making it perfect for your London itinerary.

Choose complementary colors or go for patterns to make a stylish statement. Pair with block heels or stylish mules for added flair.

• This look transitions well from day to night, ideal for exploring the city or attending events.
• Add a statement necklace to elevate your style.
• A structured handbag can complete the polished appearance, offering functionality without sacrificing elegance.

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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8. Athleisure Set with Casual Jacket

Exploring London can involve a lot of walking, so why not do it in style with an athleisure set?

A matching set of joggers and a sporty top, like the athleisure jogger set, is not only comfy but also on-trend.

Layer it with a casual lightweight jacket to keep the chill off during cooler moments.

This look is functional for sightseeing yet stylish enough for a quick coffee break. Pair with trendy sneakers, such as the trendy sneakers, for ultimate comfort.

• To keep it chic, choose color-coordinated sets.
• Accessories like a cute backpack or a baseball cap can elevate your athleisure look.
• Opt for breathable fabrics so you stay comfortable all day.

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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9. Silk Blouse with High-Waisted Trousers

A silk blouse paired with high-waisted trousers creates a chic and elegant travel outfit suitable for any London excursion.

For a stylish option, consider the silk blouse, which features ruffled sleeves and a flattering V-neck, perfectly complementing the warm tones of high-waisted trousers.

Opt for trousers in a rich shade like camel or chocolate brown, such as the high-waisted trousers that are both comfortable and tailored, elevating your look significantly.

This outfit seamlessly transitions from daytime sightseeing to evening dining, making it ideal for a busy day in London.

Complete your ensemble with stylish mules, which offer both comfort and chic appeal, allowing you to stroll through the city with ease.

To add a bit of flair, choose blouses with unique sleeves and enhance your elegance with simple stud earrings without overwhelming the look.

This outfit combines comfort and style, ensuring you’re ready for any adventure the city throws your way.

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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10. Oversized Knit with Tailored Pants

An oversized knit sweater paired with tailored pants is another go-to outfit for fall in the city. This combo strikes a perfect balance between cozy and chic.

Choose a chunky knit in a bold color, like the chunky knit sweater, which provides extra warmth and comfort, and balance it with tailored trousers, like the tailored trousers that give the outfit structure.

This look is perfect for those breezy days when comfort is key, while still looking polished.

Finish off with classic loafers or ankle boots, such as the classic loafers. This will not only complete your outfit but also ensure your feet stay comfortable as you stroll through the city.

Don’t hesitate to add a pop of color with your accessories, and remember that a structured bag can tie the whole look together.

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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11. Printed Midi Skirt with Fitted Turtleneck

A printed midi skirt paired with a fitted turtleneck creates a playful yet sophisticated look that’s perfect for London’s September weather.

Opt for a skirt with a fun print, like polka dots or florals, such as this high-waist tiered skirt, which not only adds flair but also comes with pockets for practicality.

Combine it with a solid-colored fitted turtleneck to keep warm during the chilly evenings.

This outfit is versatile enough for both casual outings and more dressed-up occasions. To keep your feet comfortable while exploring the city, complete the look with ankle boots or stylish flats.

You can also add a belt to accentuate your waist for a more polished appearance. If you’re feeling adventurous, mixing patterns can give your outfit a unique twist.

For an extra layer of style and warmth, consider elevating the ensemble with a classic trench coat, which is both windproof and chic.

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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12. Casual Dress with Combat Boots

A casual dress paired with combat boots is a perfect blend of edgy and feminine.

This outfit is practical for wandering through the cobblestone streets of London or enjoying a coffee at a local café.

Consider a casual dress featuring a relaxed fit in a warm-toned color or fun print; it’s both comfortable and stylish.

The addition of combat boots gives it a stylish kick while providing the support you need for a day of exploring. If the temperature drops, layering with a light jacket can keep you cozy.

For added convenience and flair, a crossbody bag is perfect for carrying your essentials without sacrificing style.

Accessories like a choker or statement earrings can elevate the look even further.

If you’re feeling a more bohemian vibe, consider opting for a flowy maxi dress that pairs beautifully with your combat boots.

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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13. Vintage-Inspired Blouse with A-Line Skirt

Embrace a nostalgic vibe with a vintage-inspired blouse paired with an A-line skirt, making it ideal for exploring London’s historic sites.

The vintage-inspired blouse offers a soft fabric with a charming stripe design, perfect for achieving that retro look.

Tucking it into the a-line skirt not only highlights your waist but also enhances the overall silhouette, creating a flattering and stylish ensemble.

Complete your outfit with a pair of classic ballet flats, which provide comfort as you walk around the city while maintaining that timeless appeal.

To enhance the vintage feel further, consider adding a headband or wide-brimmed hat, and layer with a cardigan for extra warmth and style during those cooler September days.

Vintage shops can also be great places to find unique pieces that complement this look perfectly!

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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14. Statement Coat with Simple Outfit

When the weather gets chilly, a statement coat can be the showstopper of your outfit.

Opt for a bold color or a unique pattern with a statement coat like this trench coat featuring a notch lapel and double-breasted design, perfect for elevating even the simplest ensemble underneath.

Pair it with skinny jeans for a chic look that ensures you feel stylish without much effort.

These skinny jeans not only enhance your silhouette but also provide comfort, making them an excellent choice for exploring the city.

Complete your outfit with a classic white tee. This timeless piece is perfect for layering under your coat, ensuring you stay warm while looking fabulous.

Play with accessories that either complement or contrast your coat to create visual interest.

A fedora or beanie can add an extra touch of style without sacrificing warmth. Look for coats with interesting textures or silhouettes to truly make a statement.

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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15. Chic Romper with Ankle Boots

A chic romper is another fantastic option for a day of exploration. Consider the chic romper available in a variety of playful patterns and classic colors.

Pair it with a denim jacket like denim jacket for added warmth as you navigate the cool September air.

This outfit is not only stylish but also comfortable for all-day wear, allowing for easy movement while you take in the sights of London.

To complete the look, opt for the trendy ankle boots, which offer both style and practicality, ensuring your feet remain happy throughout your adventures.

• Don’t forget to add a hat to keep the sun at bay or to elevate your ensemble.
• Look for rompers with pockets for added convenience.
• Choose fabrics that are breathable yet warm enough for the cool September air.

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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16. Layered Tunic with Leggings

For a super comfy outfit, try a layered tunic like the cozy knit tunic paired with stretchy leggings, such as these stretchy leggings.

This casual look is perfect for travel days or when you want to prioritize comfort while still looking stylish.

Opting for a tunic in a cozy knit allows for easy movement and gives you a put-together look.

With the added comfort of stretchy leggings, you’ll feel great whether you’re exploring the city or lounging on a long flight.

Pair your ensemble with tall riding boots or stylish slip-ons for an effortlessly chic vibe.

Choose tunics that are slightly longer for added comfort. To elevate your outfit, consider accessorizing with a long necklace for a hint of elegance.

A light scarf can also be a stylish way to keep warm, making it a great addition to your layered look.

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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17. Colorful Cardigan with Basic Outfit

A colorful cardigan can be a great layering piece for those cooler days in September. Pair it with a basic t-shirt and denim for a simple yet stylish outfit.

For this look, consider the colorful cardigan featuring a fun strawberry print that adds a vibrant touch to your ensemble while keeping everything else neutral.

This outfit is perfect for casual outings or days spent exploring markets. Finish the look with comfy slip-on shoes like comfy slip-on shoes for convenience as you wander the city, ensuring you stay comfortable throughout the day.

To tie the outfit together, opt for accessories like a bright tote bag that not only complements your look but also offers practicality with its multiple pockets and zipper closure.

A colorful scarf can also add a fun touch, while layering with a long-sleeve shirt underneath your cardigan can keep you cozy when the temperature drops.

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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18. Luxe Hoodie with Flared Trousers

A luxe hoodie paired with high-waisted flared trousers creates a stylish and laid-back look that’s perfect for travel.

This outfit combines comfort with a touch of chicness, ideal for a day of sightseeing and casual dining.

Opt for a luxe hoodie made from a soft, luxurious fabric, and pair it with high-waisted flared trousers for a retro twist.

This combination not only provides a stylish silhouette but also ensures comfort during your travels.

Complete your look with platform sandals or chunky sneakers for added flair.

When choosing your hoodie, look for interesting details such as unique drawstrings or a stylish hood to elevate the outfit.

Don’t forget to accessorize with oversized sunglasses for that touch of glamour. If there’s a chill in the air, layer on a light jacket for extra warmth.

Comfort meets chic in London! A luxe hoodie with flared trousers is your perfect travel partner—stylish for sightseeing and cozy for casual dining. Embrace the retro vibes and step out in confidence!

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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19. Printed Scarf with Simple Outfit

Sometimes, all you need is a statement accessory to elevate a simple outfit.

A printed scarf, like this soft cashmere feel scarf, can transform a basic ensemble into something special.

Pair a plain t-shirt and jeans with a colorful scarf that reflects the autumn colors of London.

Drape it loosely around your neck or tie it in a chic knot to add texture and warmth. This accessory is practical for the changing weather while also being a stylish addition to your look.

Choosing scarves in rich fabrics like wool or cashmere for those cooler days is essential, and this cashmere blend scarf offers both warmth and sophistication.

Mixing prints can create a fun and unique style, and if you’re looking to add something bold to your outfit, consider pairing your scarf with a bold patterned tote bag.

This bag not only complements your scarf beautifully but also provides practicality for carrying your essentials while exploring the city.

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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20. Classic White Shirt with Midi Trousers

A classic white shirt is forever a staple, and when paired with midi trousers, it creates a timeless look that’s perfect for a variety of occasions, from museum visits to casual dinners.

Opt for an Adult Softstyle Cotton T-Shirt for a slightly oversized fit that exudes that effortlessly chic vibe, and choose trousers that are both comfortable and stylish.

To complete your outfit, add loafers or block heels for a touch of elegance as you navigate the city. You’ll appreciate the versatility and comfort they offer while exploring London.

• Playing with different textures for your shirt, such as linen or cotton, ensures breathability.
• A belt can help define your waist for a structured look.
• Consider mixing your accessories with bold colors to keep the ensemble fresh.

A classic white shirt and midi trousers aren’t just outfits; they’re your passport to effortless style in London! Embrace comfort and chicness while exploring the city’s treasures.

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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21. Fun Print Dress with Cardigan

Finally, a fun print dress layered with a cozy cardigan is a great choice for September in London.

This outfit blends comfort with style, making it ideal for a full day of exploring.

Choose dresses in playful prints or vibrant colors that reflect the fall palette, such as the fun print dress, which offers a stylish yet comfortable fit.

Pair it with a soft cozy cardigan for warmth and style, ensuring you’re prepared for the typical London chill without sacrificing your fashionable look. Finish off with ankle boots for a trendy touch.

To enhance your silhouette, consider layering with a belt to cinch the waist and create shape.

A crossbody bag is perfect for keeping your essentials handy while you’re out and about, allowing you to explore freely.

Plus, accessorizing with a statement necklace can add an extra pop to your look, making it effortlessly chic.

Last update on 2025-08-28 / Affiliate links / Images from Amazon Product Advertising API

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Conclusion

Navigating London’s September weather in style doesn’t have to be overwhelming.

With these chic outfit ideas, you can enjoy your travels while looking fabulous.

Don’t hesitate to mix and match these trends to create looks that express your personal style as you explore this iconic city.

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Frequently Asked Questions

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