If you’ve ever stood in front of your wardrobe on a cold morning wondering what to wear, you’re not alone. The good news is that with the right coats, layers and heavier fabrics, winter can be one of the easiest seasons to pull together a ‘look’ for.
If you’re reaching for the same jacket and jeans most days, a few simple changes can make a big difference. In this article, we’ll cover 10 essential winter wardrobe pieces every man should have, along with expert tailoring advice to help you wear them well.
1. Classic overcoat
A good overcoat pulls your whole look together. Whether you’re heading to work or out on the weekend, it’s one of the easiest ways to add structure to your look during winter.
Styles like single-breasted coats work well for everyday wear, while double-breasted versions feel more formal. Pea coats are shorter and sharper, while car coats offer a clean, minimal finish that suits most builds.
Keep in mind that the proper fit will instantly make you look more put-together. This means that the shoulders should sit neatly, the sleeves should end just past your cuff, and the length should suit your height and frame.
When it comes to colour, if you want something versatile, choose a neutral colour like navy, black or camel so you can throw it over almost anything.
If you’re after more flair, forest green, burgundy or deep blue can be a subtle way to add colour to your outfit without it losing its timeless feel.
2. Layering sweaters and knits
A few good sweaters can carry you through the colder months. They’re easy to layer and comfortable to wear. Whether you prefer something chunky or more refined, the right knit adds warmth without the bulk, which makes it ideal for layering under coats or over shirts.
It’s worth looking for fabrics like merino wool, cashmere blends or heavier cotton knits. These materials hold their shape, breathe well, and feel better against the skin than cheaper synthetics.
When it comes to fit, aim for something that sits close to the body but still gives you room to move, especially if you plan to wear it under a jacket.
3. Tailored trousers
Tailored trousers are one of the easiest ways to bring shape and intention to your winter wardrobe. They offer more structure (and something different) than denim and help create a cleaner line under coats and knits, which can make your whole outfit look more elevated.
In cooler months, fabrics like wool flannel or brushed cotton add warmth while still holding that crisp, tailored finish. A slightly tapered leg also tends to suit most builds and works well with both boots and dress shoes.
If you’re between sizes or the length isn’t quite right, take them for a quick alteration to make them look brand new again.
4. Dark denim
Dark denim is a reliable go-to in winter. The dark looks more fashion-forward and can be worn in more places, like out to a nice dinner or on casual Fridays.
A slim or straight cut will flatter the legs but still feel relaxed, making it ideal for both day and night outfits.
The right fit at the waist and hem is also key to a comfortable fit. You’ll ideally want clean lines with no bunching or dragging over your boots.
5. Stylish boots
Every winter wardrobe needs at least one pair of great boots. They’re practical, durable, and instantly elevate your outfit.
Look for classic styles like Chelsea boots, brogue boots or lace-up designs with a sturdy sole for grip. Waterproof leather or well-treated suede will keep your feet dry without sacrificing style. If you pick a pair of boots with quality materials and craftsmanship, they should last you 10+ years.
To keep the look sharp, make sure your trousers are either hemmed to sit just above the boot or tailored with a slight break. (Tip: Bring your preferred pair of shoes with you when you’re getting your pants hemmed, so they’re tailored perfectly.)
6. Quilted vests and lightweight jackets
Quilted vests and lightweight jackets are ideal for those in-between days when you need warmth without wanting to feel too bulky. You can wear them as a layer over shirts and undercoats, making them perfect for both casual and business-casual looks.
Measure for a fit that leaves room for layering underneath but still sits close to the body for a clean silhouette. Also, keep an eye out for subtle textures and neutral tones like olive, navy or grey, as they will integrate effortlessly with the rest of your winter staples.
7. Wool blazers
A wool blazer adds instant sophistication to your winter outfits. It’s warm, structured and easy to layer over shirts or knits. Classic colours like charcoal, navy or brown work well in colder months, especially when paired with textured fabrics like tweed or brushed wool.
You’ll want the fit to be tailored through the shoulders and waist for a structured but comfortable shape. Try styling your wool blazer with trousers for work or dark denim for a more relaxed look.
8. Practical hats
Winter hats should serve a dual purpose. They need to keep you warm and add the final touch to your outfit.
Beanies are a reliable choice for casual days, offering comfort and ease. At the same time, flat caps create a more sophisticated look and work well in dressier settings.
It’s worth investing in quality materials like wool or cashmere blends for warmth and durability. Try to choose a shape that complements your face so the hat feels intentional and well-styled, rather than an afterthought.
9. Scarves
Scarves are one of the easiest ways to add warmth and accessorise your winter look. Wool and cashmere are ideal for keeping out the cold while still feeling soft and breathable.
Choose colours that complement your wardrobe, or go bold with a statement shade. The ideal scarf is thick enough to keep you warm but slim enough to layer neatly.
10. Heavyweight shirts
Heavyweight shirts are great layering pieces when you want structure without a full-on jacket. Flannel, brushed cotton and twill all work well in cooler weather and feel modern yet relaxed.
Go for comfortable fits with sharp details like a clean collar or box pleat for a balance of comfort and an effortlessly cool look. Earthy or neutral tones suit the darker winter months and pair easily with coats, knits and boots.
Bringing it all together
Winter dressing feels a lot simpler when your wardrobe includes a few staples you can rely on year after year. Investing in quality pieces and making sure they fit properly can help you stay warm, look sharp and feel more put-together.
If you’ve got items in your wardrobe that you love in theory but never reach for, now’s the time to give them a new lease of life. LookSmart’s expert tailors can adjust, refine and repair your winter staples so you get more out of what you already own.
Ready to bring your old favourites back to life? Find your nearest store here.
FAQs
What are the best layers to include in a men’s winter capsule wardrobe?
A good winter capsule wardrobe should include a few key layers you can mix and match. Think a wool overcoat, puffer jacket, knit jumper, and tailored pants. Add in a few base pieces like long-sleeve shirts in breathable fabrics to keep things flexible.
How do I style a bomber jacket in cooler weather?
A bomber jacket is a great in-between layer. Pair it with a knit jumper or dress shirt, depending on the vibe. Go for classic colours like light grey or dark brown, and add a scarf or beanie to make it more stylish and warm.
Can I wear suit pants outside of formal settings?
Yes, suit pants can be surprisingly versatile. Pair them with a casual knit or denim jacket, and swap dress shoes for clean casual men’s shoes to tone it down.
