What To Wear This Fall and Winter

If you already read my previous article about How to layer, then this is an updated version from it. In that article, I’ve shown you how to layer with basic tees, a little bit about hoodies and jacket, the appropriate length of the layers and colors that go well together.

In this article, I will go into more detail on layering with hoodies and other pieces in wardrobe such as flannels, leggings and high socks. Without further ado, let’s get straight into it!


Flannel + basic tee

I usually wear an elongated t-shirt inside and then, throw a flannel on top of it to create a peek-a-boo effect at the hem of layer. Peek-a-boo can be easily understood as hide and show illusion. This is also one of the main reasons to layer to create a very identification feature, layering the pieces on top of each other.


I honestly advice you to use neutral color tees to layer because what you want is the peek-a-boo illusion at the hem and torso to create a background and identification feature for your flannel, not to colorful to look like a mobile painting.

Chances your flannels are already very bright and colorful so, just tone down a neutral color basic tee, and as simple as possible.

Flannel + Jacket

The most basic outfit starts with long or short sleeve tee then, throw on a jacket on top, which is also the tradition outfit. Sometimes, it’s also the best-looking outfit. However, if you want to be more creative and glorify, then wearing a flannel will make your outfit a lot cooler and the inner flannel layer will create a very grunge, street look.


Also, a t-shirt + flannel outfit when taking off your jacket, you will still have a very good-looking outfit and stand out. Instead, if you only have a t-shirt, when taking off your jacket, your outfit will look rather monotony and simply (also awkward).

Flannel + Hoodie

This is also my favorite combo.

When only wearing a hoodie, your outfit will look very subtle. Layering with a flannel will make your outfit stand out a little more, maybe even a little more dress up.

Imagine if you walk into a bar, only wearing a hoodie, it’ll look like you just run from home straight to the bar. Instead, with the same hoodie pairing with a flannel, your outfit will immediately look more dressy, outstanding and more well-thought.

Another bonus when wearing hoodie with flannel is you can keep warm on days that aren’t too cold as you know wearing a jacket during winter, it will get cold if you take it off. On the contrary, always wearing a jacket on your body will make you feel very bulky.

Flannel by Tying around your waist

Next is layer by tying the flannel around your waist. This method is not actually layering but a way to make your outfit look cooler by having another layer popping out behind the back.


This is also the method I use to sometimes make my outfit grungier and street.

The very first one makes your outfit more neat and clean: Start by button up your flannel and fold your shirt so that the back and the arms are in line. Then, just tie up the arms like normal or putting the arms into the belt loops of your pants to let them hang naturally on your thighs.

This method is the best when wearing pants, trousers and jeans to give it a more neat and clean look.

The second is to not button at all and just tie the flannel on your waist, like you just happen to pick up the shirt and decided to tie them on your waist. You can even have the arms low and high, or the flannel being free styled up and down.

This method will give it a more grunge, street and throw back look. I call this is “dress like a rockstar”.

In general, flannel is an amazing item for fall/winter season. It’s timeless, transferable and especially will keep you warm. I also have a separate article on how to choose a perfect flannel, color variety, price points and some recommendations to inspire you to choose the right piece.



This is an essential item you cannot miss for winter. Usually, I will wear an elongated tee with a hoodie to connect my upper and lower body together. That is probably the fundamental outfit so you can layer with all types of outerwear like I previously mentioned: flannel.

And more with jackets such as denim jackets, leather jackets and bomber. When pairing with your hoodie, the jackets will look les serious, bringing a very casual, laid back vibe.

Also, with full-zip type of hoodies, you can play around with the two-way zippers, trying out different looks such as pulling the zipper all the way up to show your t-shirt underneath.

When layering, not only with hoodies, but also other garments, you SHOULD use contrast colors, meaning that the colors compliment each other to make our outfit pop, and stand out a lot more.

Of course, no one understands your outfit more than you do so, keep the balance to make it suit you because there is no mix formula. If it looks good, then rock it!


Finishing the upper body, next is to layer with leggings.


This is a smart layering way so you can get away with wearing shorts during winter. And to be honest, there is nothing more comfortable than wearing shorts.

This layering method is actually rather straight forward as it only combines of leggings and shorts. there’s nothing complicated and fancy to it. However, there is one thing to notice is the material of leggings.

There are two common types of material which are polyester and knit.

Polyester are leggings similar to the one NBA players wear with basketball shorts. This is the sportier type of leggings so it makes most sense to pair it with an athletic pair of shorts or basketball shorts.

Knit are wools, in which the most common is waffle knit. With these types of leggings, you should only wear with drop-crotch shorts made with cotton or similar knit material.

The more basic the shorts, the better because knit leggings have a lot of stack effect on the calve area, which is why you shouldn’t over-lap and create too much noise on your lower body.

To choose a top that suits the best for shorts and leggings, treat them like a pair of joggers or track pants which are very casual and comfortable outfits.

Men’s Organic Cotton Thermal Underwear Long John Pants – Luxury Base Layer

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The reason why I highly recommend this legging to you is that it’s made out of 100 percent organic cotton, which means the fabric and the texture is strikingly soft, comfortable to wear and absorbs moisture very well.

You can go wrong with TexereSilk. Their products are on point in quality. Other than comfort, this legging is also double thermal layered to give extra dryness and warmth to users.

Another good thing is their moderate length. I actually bought a lot of leggings, some of which come in short length that can’t even reach my ankles. And I don’t advise you to opt for such items as they make a little “girly” look.

I really like their tag-less label as it won’t cause irritation to our skin, especially for those guys who have sensitive skin. In other words, this piece is comfortable, soft, good moisture absorbance and durable. You can wash it by machine.

DRSKIN Men’s Compression Warm Dry Cool Sports Tights Pants Baselayer Running Leggings Yoga

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For those who are active boys, this is a perfect choice as it comes in very little weight without restriction in movement. The legging is made out of ultra-soft and smooth fabric that’s blended of 92 percent polyester and 8 percent spandex. That’s why the item is very flexible and wicking moisture quickly. Besides, its two-way air circulation will keep you cool in summer and warmth in the winter.

Not only wear in winter, you can style it with any seasons, from spring to summer and autumns for any sports like snowboarding, skiing, basketball, training, gym, etc.

But here is where the real fun begins, this bad boy has UV blocking ability up to 98.8 percent. Wow! In other words, this is a multifunctional pants.

Especially, this will be an interesting emphasis for your that-day outfit based on its grungy camouflage patterns that’s nicely printed along the pants as well as its small logo brand on one side.

Compression Pants Men – Workout Leggings for Gym, Basketball, Cycling, Yoga, Hiking – Rash Guard + Performance Running Tights – Athletic Base Layer Pants / Thermal Underwear for Men By CompressionZ

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This CompressionZ comes in four colorways: black, blue, green and white. But if you intend to layer it with basketball shorts, I highly recommend you to opt for the black as this is a safe choice to rock with multiple clothes and styles.

However, I don’t say that you can’t mix with other colors, but it’s just when you already understand how style your outfits as if you don’t, your “OOTD” will become a disaster.

In terms of material, this pant is made out of nylon and spandex so, similarly to the DRSKIN above, it wicks moisture greatly and provide good ventilation to keep us cool in summer days whereas its amazing heat retention provides warmth in the winter.

Based on its basic design, you can style this pant with many outfits, from casual to sportier clothes. It’s also perfect to accompany with you to play sports or join outdoor activities such as basketball, volleyball, rugby, soccer, gym, skiing, snowboarding, etc.

To get a more relaxing fit, you can go one size up, but for the best fit, I highly recommend you to go true size with this pant.

Defender Men’s Compression Baselayer Pants Legging Shorts Shirts Tights Running

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Compared to the other leggings made out of polyester and spandex, this bag boy doesn’t seem to have much difference. Two-way air circulation, heat retention, moisture absorbance, flexibility, elasticity and durability.

But what makes me include it in this collection is its variety of colorways. Other than dark, solid tones like black, gray, blue, there are many character and grunge designs like red, green, orange and camouflage.

Thus, if you want to be outstanding, I advise to opt for those bright tones with character patterns. But kindly keep in mind to mix them with solid color clothes or plain shorts to avoid making a confused effect.

Besides, this pant is also added UPF 30 to protect your skin from UV rays.

Fruit of the Loom Men’s Classics Midweight Thermal Bottom

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Fruit of the Loom is a reliable mid-range brand that I sincerely advise you to try, especially if you are a newbie to streetwear. Their products are truly bang for your buck with amazing high-quality contrasting to its affordable price tag.

This piece is made out of cotton and polyester so that it’s not only flexible, good moisture absorbance, but also soft and comfortable to wear. Besides, based on this material, you can feel ease in mind to machine wash it. But kindly remember to not use the dry mode to maintain its form.

To bear cold weather of winter, the pants are added Warm waffle thermal at the bottoms to retain heat as long as possible. Besides, like the TexereSilk, it is tag-less to prevent irritation to our skin.

High socks

And lastly, layering with high socks!


Honestly, they aren’t at all something new and is also not a type of layering but, this creates and illusion for your lower outfit to color block, meaning it breaks your body into parts and showing the layers.

For example, when you wear track pants or joggers. If you don’t want your lower body to look too simplistic, then wear a pair of high socks and pull it all the way up. Don’t forget to tuck your pants inside these socks. First of all, this will keep you very warm. Besides, you can put your feet up, chill up on the coach, basically free of movement without afraid of having your ankles exposed. Particularly, it will make your sneakers look great.

Depending on your legs and length of your pants to adjust the socks high or low

MUSAN Wool Ski Socks ,Extra Warm Knee High Performance Snow Skiing /Snowboard Socks in Outdoor,Fit for Men and Women

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The safest choice when it comes to choosing a pair of socks for men is black, grey, and navy blue as it can easily style with different shorts and leggings. However, for some interesting emphasis but not overlooked, you can opt for these Musan socks.

They are made out of blended material including cotton, wool, acrylic, polyester and spandex. Such a variety of fabrics has come up with multifunctional socks to fit with different weather, different activities and purposes.

In fact, there are many customers bought it to use as a pair of ski socks based on its striking softness and warmth. But meanwhile, its outlook is still outstanding enough to style with. As I said, you can adjust it high or low, tuck your pants inside it for a character and stylish look.

This colorway is perfect to match with basic and classic outfit like black legging, grey shorts or black set of clothes.

Men’s Cool Colorful Casual Socks – Novelty Funny Casual Combed Cotton Crew Dress Socks Gift Pack

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If you want to show up a bit of your personality and characteristics to the public, let these colorful street style socks help you. They are sold by combo, each of which includes 4 pair of socks coming in different bright tones of color to easily make you stand out from crowd, especially when you tuck your pants inside it and pull highly.

In terms of functionality, these guys are made out of Combed fine cotton that delivers a soft feeling touch. Besides, it absorbs moisture or sweat quite well to keep your feet stay fresh all days as well as eliminate odor as best as possible.

You also don’t need to worry about its warmth-keeping ability as nothing can beat against cotton in this field. Also, if you are looking for a small yet meaningful present to a streetstyle die-hard friend, look no further than these vibrant socks. Surely, he will love it!

HSELL 6 Packs Men Color Dress Socks Funny Colorful Rainbow Argyle High Fun Sock,Multicolors,One Size

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HSell is one of my favorite brands specialized in socks for men. Their products’ design is uniquely one of a kind with vibrant and lively colorways to easily make you stand out from the crowd.

Don’t think that this is a challenging pair of sock to style with. On the contrary, it’s multifunctional enough to mix with different clothes and styles. You can mix it with either basic or patterned outfits (but just try mixing them with patterns when you already know how to style), from streetwear to vintage look.

With streetwear, you can pull it high or low, tuck or untuck your pants into it, as no matter which way you’d prefer, the socks will be an elegant yet impressive emphasis to your outfits. The same thing with vintage style, you can roll up the pants a little bit to let these socks be exposed.

Talking about functionality, these guys are quite warm, comfortable in winter whereas breathable and soft in summer to provide the best experience to the users. The key characteristics is that they are made out of 90 percent cotton and 10 percent polyester. But the real fun is that it’s 200-Needle Combed fine cotton.

And on top of that, Hsell provides 30-days money back warranty as well as their customer service is truly good.

And that’s everything you need to know about layer in this fall/winter season. There’s actually one thing you want to advise you which is don’t treat fashion like a math formula as there isn’t a right or wrong. Just take it easy, experiment and test what suits you the best. One last thing you need to keep in mind is that streetstyle was born to break any boundaries and status quo. No one in the world has the right to judge you so, just proudly rock whatever you like the way you like.

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