You wake up in the morning and there it is – looking through the window you see the ground is completely covered in white. Well, you suspect it was white, maybe few hours ago, by now it’s a combination of white, brown and, if your neighbors own a dog or two, yellow – lovely.

It’s dark when you leave the home in the morning and it’s dark when you come back home from work or university.

Then there’s cold… With a slight smile you remember warm summer days when you had outdoors fun with that adventurous girl. What was her name again? Meanwhile, you’re adding layer after layer of thick fabrics just to keep your Johnny from freezing.

And as you walk out the door you get a glimpse of yourself in the mirror and realize you look like that damn Michelin mascot.

It’s winter time!

But is it really all THAT bad?

How To Dress Sexy In Winter

Every season brings its distinct set of challenges and perks. For all the annoyances of winter mentioned previously, we should not forget how effective “Hey, let’s get out of the cold, I have some hot wine at home” and “Oh, you’re cold? Come here under the blanket” lines become.

Then there are those international I’ve-got-drunk-and-slept-with-a-colleague/friend/classmate holidays – Christmas and New Year, so it’s not all that bad.

Even more so, we finally can pull out our sexy knitwear, cool scarfs and display our epic layering skills without looking try-hard. Hey, it’s cold! I’m wearing this perfect combination of fabrics, patterns and colors to stay warm!

Now, back to clothes.

The ultimate goal of dressing in winter is to keep warm without looking like a huge bundle of clothes mashed together. It’s relatively easy in 0 to -10 C temperatures and gets exponentially more difficult as we reach -15, -20, -25 C and below (at a certain point pretty much everyone except Scandinavians say “fuck it, I’m wearing everything I own!” and that’s perfectly fine.)

When it comes to dressing sexy in winter, we need to consider few things:

  • Layering is your go-to strategy. This is especially great for skinny guys as they can use this to appear quite muscular all of the sudden.
  • Whenever possible, avoid adding layers that have excess fabric around torso (pockets, loose cuts, etc.) – we need to maintain proper, attractive proportions.
  • If you’re a skinny jeans kind of guy (this often also applies to slim fit jeans), pay close to proportions between upper and lower body. We often add tons of layers on our upper body, add a loose coat on top and then wonder why our legs look like tooth sticks compared to the rest of the body.
  • It’s time to pull out your epic boots. Seriously, a solid choice in boots can fix even a very mediocre outfit. Consider adding thicker socks too as keeping your feet warm is the first step to keeping your whole self warm.
  • Scarves, scarves, scarves – the ultimate winter accessory.
  • Colors in general should be more conservative in winter, though one or two bolder details are perfectly fine and actually preferred to differentiate yourself.

Lastly, we need to remember that when our goal is to dress sexy in winter it’s a given that we won’t spend a lot of time outside – we’re going on a date, to a bar, house party or some other indoors location (I dare you to do day game when its -20 C outside haha!). Which means any outfit we build should seamlessly transition from bulky winter outfit to one that’s lighter, comfortable, doesn’t restrict movement and, naturally, presents you in the most attractive light without top layers too.

When looking through this style inspiration keep in mind that you might need to adjust to how cold winters are in your particular location, add / remove layers, use thicker / thinner fabrics accordingly (this also applies to shoes, some of you can get away with regular designs as long as you wear thicker socks, others will need to look for a pair that’s lined with fur & the thickest damn socks your grandma can make.)

About hats and gloves:

I don’t like hats – there, I said it. A stylish haircut will outperform any beanie, cap or any other style of hat. Yet, having your ears frozen is not exactly a fun feeling so I’ve included suggestions for hats in couple of the looks.

Don’t over-think gloves – keep it simple, a pair of black leather gloves (or dark brown) will take you a long way and even though it is possible to get extra style points for gloves, more often than not you’re better off sticking with the simplest option.


As layering is such an important part of dressing in winter I’d like to quickly remind you the basic guidelines:

  • Thinner fabrics go first, thicker on top.
  • Skinniest pieces go first, looser pieces on top.
  • Brightest items go first, darker pieces on top.

These are just guidelines, but its good to keep them in mind.

Now, let’s get started, shall we?

Unwrap Your Present, Sweetie

sexy winter 1 2014
This is our sexy – classy outfit for winter. Not exactly an image that screams “rebel yeahh!!” but does its job perfectly when we need to look like we have our life together even when the coat comes off. As you see we have two dominating colors here: blue and grey, with a touch of black and white to spice it up.

Coat – Navy wool coat, medium length. As we’ll need to fit a blazer underneath go for a regular cut instead of something that’s cut close to the skin. Keep it simple, keep it smart – unnecessary details would not improve this look.

Blazer – slim fit cut, grey (I picked a dark grey option, but a lighter shade is a perfectly good choice too). We need to avoid loose fabric, especially around hands and shoulders.

Waistcoat – this is the piece that makes this outfit stand out. We’re going for a slim cut, lighter shade of blue / navy. When combined with an otherwise dark outfit, this piece will really stand out after coat is off and blazer unbuttoned.

Shirt – white dress shirt. Keep it simple.

Chelsea boots – Again, we’re looking for a clean and simple design, in black. This is one of the few cases when we don’t want boots to steal the spotlight.

Trousers – grey, smart pair. Adjust cut according to how tight your upper body is, though generally you’ll mostly be going for slim fit.

Gloves – black leather gloves, don’t overthink it.

Belt – black leather belt. You might notice that I picked one that has a sort of golden shade at the buckle. This was done on purpose, even though it’s not mandatory, I wanted a minor detail in different color just to break the pattern.

Scarf – we want to match our scarf with our grey details (for example, trousers), the fact that I managed to find one that also has a dark blue highlight is just a bonus. For winter your scarf should be rather thick.

Best suited for: dark colors and a waistcoat are great for everyone who want to appear leaner. Medium length coat means that it’s less than ideal for guys of shorter stature (consider swapping for a pea coat). As for venues, you would look a bit out place in a rock bar, but most classy and semi-classy venues would be a great date location.

A Cheesy Line To Go With The Look: There’s a big, thick, cozy carpet at my place, just by the fireside. Let’s light it up and see if you’ve been a good girl this year.

I’m Cool, Not Cold

sexy winter 2 2014

Some men are just bad to the bone, they don’t care if it’s summer, autumn or winter – they are wearing their sexy leather jackets no matter what. But what happens when those bad boys also develop a sense of style?

Well, dear friend, it’s a beautiful mash of “zero fucks given” and self-amusement with a strong aftertaste of badassery – seemingly effortless execution and no woman can help herself but check him out.

Sweater – patterned sweater in burgundy (other colors can work too, just avoid the safe ones like grey, brown, black). You’ll most often will be going for regular cut, but skinnier guys can look for something cut closer to skin too. V-cut for neck is perfectly fine too. In length, sweater should end around your belt line as we’ll be wearing our shirt untucked. Quick note regarding patterns on sweaters – ideally you want to go for a piece that has its patterns around your chest line instead of covering it all, this way it will create a more flattering visual effect.

Shirt – Casual / smart white buttoned shirt, worn untucked. Alternative – white tee.

Leather jacket – winter ready (read thick and lined) black biker jacket, quilted or not is optional, fur coating around neck – preferred. Now real leather jackets suitable for winter can be very expensive and considering it’s something you’ll only be wearing in winter I don’t think it’s worth the investment unless you really can afford it.

Jeans – Dark blue jeans, a slight wash / distressing – preferred. A skinny cut would be ideal for this look, but we need to be careful with those as they tend to be less than awesome at keeping you warm. Adjust according to your actual situation.

Boots – Black, rugged work boots. Combined with leather (leather-like) jacket, those are the pieces that make this look worthy of a man, who really does as he pleases.

Scarf – Dark blue, medium-weight or bulkier design.

Gloves – you could go ahead and pick something with extra spice like wool mittens in burgundy or dark blue, but in all honesty, in most cases you’d be better off with a black pair of leather ones.

Hat – this is one of those few looks where a beanie actually would go well. That is, as long as picked right. I matched it with the sweater, so it would look very impressive with jacket unzipped.

Best suited for: Not ideal for bigger guys, but a particularly flattering combination for guys who want to appear more muscular, stronger. The brighter colors are not that intrusive as to create high contrast between upper and lower body so with the combination of badass work boots it’s a solid option for guys of shorter stature too. In contrast to our first look, this outfit might be a bit too “fuck yeah!” for classier venues but would work like magic in most bars and pubs.

A Cheesy Line To Go With The Look: I’m keeping my jacket and boots on! Other than that, do what you please.

Dear Santa, I’ve Been Bad And I Liked It

sexy winter 3 2014
I guess we could call this our elegant-edgy option but where exactly this outfit will stand on this spectrum will depend on the exact pieces we’ll choose, few minor changes can push it way into edgy and rebellious or into elegant and safe. Our two main colors here will be black and brown with a honorable mention to white, purple and grey – each color serving its purpose.

Coat – grey coat with brown faux fur. As we’ll be layering closer to the body in this look, feel free to step away from regular cut into something slimmer. Any extra details, like military design, would push you away from elegant ant into edgy – proceed with caution.

Shirt – purple dress / casual shirt. Keep it simple. Can be worn either tucked or untucked (I’d prefer untucked.)

Sweater – black and white, patterned, slim cut. V-cut is a very viable option too.

Jeans – black, slim fit jeans. Any wash and/or distressing would push you into the edgier zones.

Boots – brown work boots. Avoid overly rugged designs. Ideally you’d want to match shade of brown with the fur on your coat – would look spectacular!

Gloves – black or brown leather pair. Don’t overthink this.

Belt – brown leather belt. Match with shoes.

Scarf – white, medium-weight scarf.

Best suited for: This look would appear most impressive on skinnier / average build guys (and of course our fit friends), but due to chosen colors bulkier guys would get away with it too. Based on height, as with first look shorter guys should consider picking a shorter coat. As for venues, you can pull it off pretty much anywhere.

A Cheesy Line To Go With The Look: It seems I’ll be unwrapping my present early this year.

Alright, Come Here I’ll Keep You Warm And Safe

Sexy winter 4

Our manliest look this winter – leather jacket, fur, thick knitwear, plaid shirt, work boots and rugged pieces – it has it all. To avoid looking borderline intimidating we’re moving away from really dark colors. We want to show that we have a fun side too. Now, I didn’t add a scarf for this look and if you’d like to wear one I’d go for a white or grey (match with hat) one.

Leather jacket – Brown leather (leather-like) jacket with faux shearling. This particular piece is in relaxed fit, but for most of you regular cut would suit much better.

Cardigan – grey knit cardigan, medium weight, regular cut. In winter knit cardigans are great for adding volume to all the right spots (read: shoulders.)

Shirt – white, plain V-neck. Going for a printed tee is a valid option for guys, who want a more hip look.

Plaid shirt – plaid shirt in cotton. Note the color scheme – each color works very well with the rest of the outfit.

Jeans – blue slim fit jeans (as you know slim cut varies from brand to brand, you want to keep at the looser end of the spectrum). Some wash / distressing preferred. As we’re wearing quite a few looser / thicker layers on our upper body we need to stay away from really tight cuts to maintain attractive proportions.

Boots – brown work boots. Ideally similar share as jacket.

Belt – dark brown, rugged, leather belt. Wide. Note that we don’t want to match it with jacket / boots. We’re purposefully picking a darker shade of brown to break the pattern.

Beanie – grey beanie. Don’t over-think this.

Gloves – dark brown leather gloves. Ideally similar shade as the belt.

Best suited for: I wanted to make sure to include at least one look that would appear most impressive on bigger guys (assuming muscle is part of that extra size) and here it is. Bright colors are not exactly visually slimming but if cuts and fit are chosen right, one would appear strong instead of sloppy. Skinnier / average guys can also pick this outfit without problem. One thing shorter guys should keep in mind is that your looser layers should not be much longer than your belt line and belt itself should be slimmer – let’s leave covering your butt / legs and wide belts to taller guys. As for venues, day time, bars and pubs would be ideal.

A Cheesy Line To Go With The Look: Come sit on my lap and tell me how you want to be taken for Christmas.

Final thoughts

It’s been few weeks since I wrote last style inspiration and I must say – I missed it! Hopefully by know you’ll have a much better idea how to keep warm without sacrificing sex appeal.

Now, few disclaimers as per usual:

  • Be smart.
  • Clothes are chosen as examples, adjust based on your budget. Ideally, find similar items to test them out before buying something.
  • Adjust based on how hot / cold it is where you live.

Deal? 🙂

For more inspirations:

And If you need personal help to make sure you’ll get it just right? Check out the consultation page

Project “Become A 9+” And SSfJ Inner Circle

As promised in the last article How To Become A Very Sexy Man – today we’re opening doors to our SSfJ Inner Circle secret Facebook group.

This group will serve as the primary platform for our 6 months project “Become A 9+” and I must say I’m very excited about it (and I know some of your are just as excited as myself! 🙂 )

To learn more about the project, our secret group and how to join it – check our SSfJ Inner Circle page.