Monsoon creative director looks at options for dressing well in a challenging autumn
Following the UK’s ‘wettest week in two years’, navigating the unpredictable shift into autumn dressing can feel like a sartorial challenge.
From overlooking the nuances of transitional dressing to losing your silhouette beneath heavy layers of clothing, there are a number of common styling mistakes that can undermine an otherwise well-considered autumn wardrobe.
This inspired Caroline Jackson, Creative Director at Monsoon, to reveal the most common autumn styling mishaps and how to avoid them.
8 autumn styling mistakes (and how to fix them)
- Impractical footwear
Autumn might feel like the right time to wear a pair of suede, heeled boots or cute ballet flats, but get caught in the rain or step into a puddle and your feet are going to be damp for the rest of the day.
Not wearing the correct footwear is one of the biggest mistakes you can make in autumn when the impulse is to wear your cutest shoes. Aesthetic as they are, these shoes often lack the sturdiness and warmth required to face the ever-changing forecasts.
Caroline Jackson shares her tips: “My advice is if you’re planning on doing a lot of walking outdoors, it’s best to go with a sturdy boot, preferably leather and black as they’re likely to go with everything you already own.
“You should prioritise practicality over style, but that doesn’t mean your shoe choices have to be un-fashionable. When paired with the right dress or jeans, a substantial boot can look chic and put together.”

- Clashing combinations
The colder temperatures means we’re dusting off our winter coats, but the desire to stay warm and dry can often mean a sacrifice of style. A beautiful dress can easily be ruined by the wrong coat, especially if you’re a fan of the dry robe.
But the two don’t have to clash, if you know the right way to wear them.
“Staying warm is important during these colder months, and being sensible where clothing is concerned doesn’t mean you have to neglect looking put together.
“A sure-thing coat that will work with everything is a faux fur coat or a trench coat (prefably woollen to keep you warm), these two keep you feeling snug whilst also not ruining your entire outfit.
“When paired correctly with either a midi dress or a mini skirt and tights, the coat can actually elevate the look.”
- Windy-weather wardrobe mishaps
Autumn brings with it some turbulent weather, and the last thing you want to experience is being up-skirted by a rogue gust of wind.
The fluctuating temperatures can create problems too, you’re often stuck between being too hot and feeling too cold because of the way clothing can trap and retain heat.
“Windy weather is probably the most annoying when it comes to styling. Wear something too thick and woollen and those intervals of still weather will have you sweating, but if you choose something too loose, you risk it blowing awkwardly around you or coming untied.
“If the forecast is reporting a particularly windy day, best to layer with light, breathable fabrics (like cotton items) that you can take on or off easily. Resist the urge to wear anything too elaborate or flimsy, because it won’t keep you warm and it creates more faff than it should.”
- Getting caught in the rain
We’ve all experienced it; headed outside on a clear, brisk day and twenty minutes later you find you’re caught in a deluge without a coat or umbrella. Though they may look good, a light jacket or thick jumper or hoodie isn’t going to protect you from the rain.
Wet fabrics can change weight, trap moisture and cause discomfort, so it’s important to dress appropriately.
“Autumn weather can be so unpredictable, so it’s best to plan for all contingencies.
“Fabrics like denim and heavy cotton can absorb large amounts of water, saturated clothes lose their natural shape and cling to the skin. Investing in a good quality waterproof trenchcoat or a wax jacket are simple ways to still look good, but avoid getting completely soaked every time you leave the house.”

5. Fabrics that crease and cling to your body
Some fabrics are prone to creasing or clinging because of how they interact with moisture and electricity. Polyester and nylon blends can hold unwanted creases or pressure marks, leaving your outfit looking rushed and messy.
“If you want to avoid fabrics that crease and cling to your body in unflattering ways, then consider wearing something like chiffon, merino wool or double-knits.
“Chiffon is naturally light and airy, and it falls in smooth clean lines that don’t stick to the skin, merino wool is known for its natural elasticity, it doesn’t wrinkle easily and doesn’t generate heavy staticity, and double-knits are excellent for autumn because the thicker, structured fabric has enough weight to hold shape whilst also resisting creases and avoiding clinging.”
6. Layering and proportions
When layering in autumn it’s important to get the proportions correct, for example wearing a long jumper with a cropped coat and you can end up looking awkward and messy.
Layering is an excellent way to stay warm and dry during these colder months but there are ways to do it without looking like you’ve dressed in the dark.
“Maybe controversial, but I find in autumn it’s always best to lead with your choice of coat first and determine the rest of your outfit around that.
For example, a cropped puffer coat styles nicely with a pair of high-waisted jeans, but you want to avoid matching it with anything that falls below the waist. If you’re wearing a mid-length dress, this should be paired with a long trench coat.
“Getting the right proportions can make the difference between an outfit that looks good, and looking sloppy.”
- Accessorising incorrectly in the colder months
Hats and scarves are a great way to keep warm in autumn and often pair well together, but get an awkward combination of colours or textures and the entire outfit can feel disjointed.
“When accessoring in the colder months, try to match patterns, textures and colours as a baseline as a woollen bobble hat isn’t going to look right against a cream cashmere scarf.
“If you’re keen to experiment with your style this autumn and find you only usually wear neutral shades, a subtle way of adding a pop of colour to your fits could be a colorful hat or scarf. It’s subtle but can make a real impact.”
- Mismatched tights
Something that may seem trivial, but can change the entire look of an outfit, is a pair of tights… Autumn is a great time to experiment with some more outlandish or wacky styles, but it can be harder to pull this off, especially if this isn’t something you usually do.
The wrong choice of pattern or colour can make an outfit appear clumsy or gauche.
“Tights are a fun accessory to include in your autumn wardrobe, but there is a knack for making them work. Coloured tights can look chic when paired with a simple black mini dress, but throw them together with a vibrant dress and you can risk looking messy.
“If you’re opting for something interesting then let it do the talking, the rest of the outfit should compliment it, not compete. A good way of experimenting with tights and still wearing something bright is to choose a pair of black or brown patterned tights, this way you avoid clashing.”








