I get it…
You don't wear suits all the time.
And when it gets cool out…
you need something casual that will look great.
I gotcha covered!
But first…as always, let's talk about the “why” of these pieces.
So – why are these 10 items the essentials?
Well – the fabric is PERFECT for spring, winter, and fall…(descriptions of fabrics at the bottom)
the fit is great…
they're ALL interchangeable.
In other words – it fits my style pyramid to PERFECTION.
So here are my top 10 picks for casual (cool weather) wardrobe essentials.
This post was brought to you by Territory Ahead.
Did you see that BEAUTIFUL rugged sports jacket from the video? Awesome – right? 🙂 Like I said – they fit my style pyramid perfectly (fit – fabric – function)…
The shirt jacket comes in handy during autumn and the early stages of winter. It’s technically a shirt but truly feels more like a jacket. Its rugged look emphasizes masculinity – which makes it fitting for a “tough guy” image.
This type of shirt is typically made of heavy weave cotton and is woven very tight. It makes a great layering since it provides enough protection against slightly cold conditions.
You want a jacket that’s made of 100% cotton and is both water- and wind-resistant. The trick is to lay it over a t-shirt or henley in a way that both layers complement the style of one another.
Henleys are the collarless equivalent of Polo shirts. They normally have a placket that’s about 2-3 inches long and are designed with 1-5 buttons in total.
A long/short sleeve henley is perfect for whenever you’re chilling inside a café or restaurant (with your jacket removed).
The softer cotton fabric makes it a great inner layer – which doesn’t feel as warm as when you wear a dress shirt or button-down. It’s also way more fashionable than a t-shirt.
If you’re looking for an alternative, the Pique Polo shirt works fine too. Both these types of shirts – if you can find the right fit – provide enough warmth while still being able to flatter your body. These shirts can also be worn comfortably in lukewarm parts of the year.
To be clear: casual button-downs are NOT the same as dress shirts. They’re more flexible in terms of environment.
They’re also designed with a more relaxed fit compared to dress shirts. There’s about 1 inch of extra fabric in both the chest and waist areas, and an additional half-inch in the shoulders.
So when it comes to casual button-downs, there are 3 things that you want to consider carefully:
You might like to experiment with a bright-colored button-down. The idea here is that when you’re walking outside, most of the shirt is covered by a jacket or outer layer. BUT you can draw some attention to the neck area through a distinctly bright collar. It’s similar to a bright-colored necktie that’s paired with a dark suit.
However, if you’re more into a rugged feel, you can try out a dark blue or olive green button-down. You can also have the sleeves rolled up so you can accentuate that outdoorsy look.
One key feature that you want to think about is the pockets – which make a huge impact on the overall style. You can go for double breast pockets to build up your chest area.
Or if you’re into a military kind of look – a button-down with epaulets will make perfect add-ons. You can even try a contrasting button color to balance out the color of the fabric.
There is a wide range of fabrics that suit casual button-downs – dobby, flannel, chambray, chamois and velvet. They directly affect the pattern and texture of your shirt. Check out the glossary below to learn more about these fabrics.
V-necks are the most flattering t-shirts for men who are shorter in size or have narrow faces.
They expose more of your neck to give the illusion that you’re taller, or that your face has a wider shape. And unlike crew necks – they have the ability to draw more attention to your face and chest.
Your best bet is a V-neck with a heavier weight fabric. This will make a nice layering piece that helps keep your torso warm. In terms of color – you may find it easier wearing a dark color since it’s less likely to clash with your outer layer.
But ultimately, choose any color that can stand on its own (especially at an indoor event) and which you’re confident wearing. I would avoid white though – it might your t-shirt look more like an undershirt.
The sports jacket exudes this outdoorsy, sporty vibe that contrasts with the formalness of suits and blazers. Here’s an article for you to get a better understanding of the difference between a blazer, suit, & sports jacket.
The best sports jackets out there are made of fabrics like twill or tweed. “Rugged” is the key description – as history shows that they were initially made as hunting clothes. The roughness of the fabric allows the jacket to take a beating for a long period of time.
Make sure you pick one that’s specifically winter-resistant. You should also be comfortable wearing it when it’s just drizzling outside.
Sports jackets often come in shades of blue, green, brown and gray. It’s also common to find them in checked patterns – which highlight that lumberjack image. But the important thing is that it has a looser fit than your suit jackets.
Textured sweaters offer you patterns with intricate designs.
You can actually keep them on when you’re indoors – as long as you feel comfortable. And since the sweater covers up the majority of your shirt, that means the shirt doesn’t have to be super stylish.
You want a sweater that can build up your arms and chest area more, so try a heavier weave instead of a lightweight kind. The fabric should be coarse or ribbed cotton (or wool). The only downside to this is it might make the sweater harder to layer over – depending on the size of your jacket.
I specifically enjoy wearing cardigans for that very reason. Not only are they the type of sweater that closely resembles a jacket – they function like them too.
They open down the front and have buttons along the edge. They can be worn either open or closed. Cardigans are also known as “three-season” garments – useful throughout the year except for summertime.
You can refer to this guide to men’s sweaters to find out other styles that might work for you. Also check out the infographic at the bottom section which shows 5 of the most attractive sweaters types.
Here I’m assuming you have at least 1 good pair of jeans at home. And while it does come in handy all the time, there are other styles of pants you might want to explore. They’re typically made of unique fabrics.
Some of the best alternatives include corduroy, cavalry twill, and classic twill trousers. These are meant to handle the cooler weather.
Corduroy, in particular, is made up of wales which are effective in trapping air to keep your warm.
Meanwhile, cavalry twill is very durable (a tougher material than denim). It withstands loads of washing without going through much wear and tear over time.
Of course, we can’t forget about footwear. This is the time when you want your feet as protect and supported as possible. So owning a nice pair of casual boots is a no-brainer.
There are 2 major styles of lace-up boots you want to pick from. The first is the Chukka boot – designed with rough-looking leather that gives off a strong, masculine appeal.
They also feel light to walk around in. If you’re aiming for the most versatile option – get a dark brown pair of Chukkas. They practically go with any of your casual outfits.
The other style is the Weatherproof Higher Lace Up – the ankle-high version of the dress shoe. This boot has a combat type of origin, as shown by its extremely durable sole. It gives your feet a good grip of the ground in order to lessen your chances of slipping.
These boots can withstand long hikes through the snow, while still looking good enough to wear in casual places. In terms of color, either black or brown will work fine.
If you want to take your casual style to the next level, try adding a classic jean jacket. The good thing about it is it matches well with everything but an identical pair of denim jeans.
So you can actually wear dark- or light-colored jeans, but you’re better off mixing and matching the jacket with other pants (see #7).
One notable thing is it’s useful for most of the year. Some call it a “three-season” wear, similar to the cardigan. But another advantage – which is also the reason jeans are still popular these days – is it’s very low-maintenance. It can get “beaten up” the way that other more delicate fabrics can’t.
If your jean jacket is made of pure cotton denim, you can wad or fold it without worrying about wrinkles. So you can literally hang up your jacket after wearing it one day, and be ready to wear it again the next day. But you also need to understand how to make the best choice of jacket.
Finally, every guy should have a clean-cut hoodie in his closet. I know – not a typical piece right? But hear me out.
It’s important since it makes a great second layer (you can throw it right underneath a thicker piece like a jean jacket) and a tool to cover your head when it rains.
You’ll find it very useful during rainy parts of the year – and it still provides warmth like all the other essentials in this list.
And don’t underestimate how stylish a hoodie can be. These days, some men don’t even wear suits or dress shirts to work – like those in the tech industry. Just look at what Mark Zuckerberg typically has on. If you wear your hoodie with style, it will only boost your confidence and “coolness.”
Casual Cool Weather Outfit Ideas
Here are some great outfit ideas that can incorporate some of the pieces above
Take Note: Different Fabrics & Their Definitions
- A variation of the plain weave in which 2 or more threads weave alike in both warp (down) and filling (across) directions, joined in the regular order of the plain weave. The name comes from its basket-like weave pattern.
- Comes from the process for woven or knit fabrics in which brushes or other abrading elements are used to raise a fuzzy or downy surface. Brushed fabrics have a soft, broken-in feel.
- A strong, rugged cloth made with a raised cord on a 63-degree twill weave. It’s designed with a somewhat coarse rib effect.
- A general class of plain weave (usually cotton) that’s made with a colored warp and white filling. It’s made often with blue and white but also available in stripes, checks and figured patterns.
- A tight, wind-resistant cotton weave that’s used for a soft and durable garment.
- A fabric with a shimmery diagonal weave which is used to form richly textured shirts without compromising formality.
- A strong, durable fabric with cotton ground and vertical cut-pile stripes (wales) which are formed by an extra system of filling yarns. The foundation of the fabric is either a plain or twill weave. It’s the warmest of all cotton fabrics.
- A term for fabric that’s woven on a special dobby loom – which enables the weaving of small, geometric patterns. A dobby weave has a more intricate and ornate appearance than a plain weave.
- A brushed fabric that's made from cotton, wool, synthetic fibers or blends. It’s woven in either a plain weave or twill weave pattern. It’s good with trapping heat and is typically used for cold weather.
- A fabric that’s knitted from fine yarns – resulting in a lightweight shirt with a bumpy texture. It’s traditionally used for tennis and Polo shirts.
- A traditional staple of men’s casual jackets, trousers, overcoats and outerwear (and also wool shirts, gloves and caps). Its name comes from the River Tweed in Scotland. You can read this article to learn more about tweed fabric.
- A luxurious fabric that’s made traditionally from silk (but can also come from cotton or synthetic blends). It’s woven on a special loom which is dedicated to producing velvet.
- A broad term that applies to all hairs of animals – mostly sheep (but also Cashmere and Angora goats, camels or llamas). It’s an in-demand fabric in tailoring, even though synthetics nowadays serve as a lower-cost alternative. The most sought after wool has a very thin diameter (10 to 20 micrometers), a length of 2 to 5 inches), and the fibers are free from any defects. This article has more details on wool in menswear.
This post was brought to you by Territory Ahead.
The fabrics they use and functionality of the clothing fit my style pyramid perfectly (fit – fabric – function)…
Oh BTW – here's a discount code: TA25RMRS for 25% OFF
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