This week US is be celebrating Thanksgiving and even though I’m from Europe and don’t officially celebrate this holiday, I definitely have a lot to be thankful for.

For example, earlier this year we did an experiment “Become A 9+” where our goal was to see how much we can improve our appearance (every aspect of it) in 6 months.

And even though I didn’t manage to get the infamous 9+ rating (on a 1 to 10 scale) just yet, this project gave birth to something I’m much more thankful for – our SSfJ Facebook group.

In its original inception the goal of this group was to provide dedicated and motivated group of men a platform to support each other as we were improving our appearance throughout the 6 months “Become A 9+” experiment.

After the experiment was completed (for now), we invited more people from SSfJ readership to join the group and I would say started having a bit more fun with the discussions about style, appearance and some other things.

One really cool thing that we had going for the last few months was a Style Inspiration contest, where we would think of a challenge (like build an outfit with a particular item of clothing) and everyone from the group could share their creative outfits. Afterwards we would vote and pick a winner for that week.

I remember the moment when I saw the first submissions on my Facebook newsfeed – “Damn, I have to bring my A game just to keep up!”

Its actually very motivating to see that reading the step-by-step guides and “how to dress” style inspirations on this site translates into improved eye for style and clothing.

With this article I would like to share the winning outfits we had in our FB group. I will also add comments why certain things work, for whom and in what situations these outfits would work best.

By the way, if this sounds fun and you’d like show off your mad outfit creating skills or just want to join a group of cool guys with whom you can talk about style, appearance & stuff, I will share the details how you can join us in the last part of this article (it’s free too!).

Without further ado,

SSfJ Inner Circle Presents: Our First Very Special Style Inspiration!

1st Challenge: No-Holds-Barred

Our opening challenge was quite simple – the only rule was that there are no rules. But even though variety of styles were submitted I’d say that the winner of the first week’s challenge summarizes the spirit of SSfJ perfectly – masculine, edgy, rugged, unapologetically breaking all the rules and very sexy.

1st challenge

Edgy / Masculine – Rugged

Details to note:

As you can see the outfit is built around dark, washed brown as its main color. Grey tee and washed black jeans are used as mostly neutral items while blue extra-long hooded cardigan is there for its attention grabbing and differentiating qualities.

If we were to take away the hooded cardigan from the equation or replaced it with something more standard (like regular length knitwear or buttoned shirt) the outfit would still look great but it’s the fact what we are breaking the layering rules (having the longest layer by a big margin in the middle) and still look great doing it, that makes this outfit so damn impressive.

Other than that, two important items that makes this outfit jaw-dropping hot are leather jacket and boots – both items are incredibly good-looking.

Best suited for:

I’m sure I won’t shock anyone by saying that the look is best suited for bars and indie/rock crowd – it’s a badass look! That said because of the chosen colors (washed dark brown is less intense than let’s say stark black), it’s very possible to pull it off successfully in the afternoon too.

In terms of personality it’s a masculine look that doesn’t have that many feminine items so most personality types can get away with it as long as you don’t mind attention – execute the outfit right and I can guarantee that you’ll get plenty of comments and compliments from pretty women in bars.

Lastly, body type.

Because we’re using an extra-long hooded cardigan its not really suitable for shorter guys. If that’s you stick with regular length buttonless hooded cardigans (just slightly longer than your short cut jacket) and you’re good to go.

Other than that the outfit is quite forgiving. Very flattering on tall & skinny guys as thicker cardigan will add some needed volume to their upper body.


2nd Challenge: Sexy Blue Shirt

After the first week where we let our imagination go wild, the second challenged was meant to see how good we are at building an outfit around a specific item – in this case a blue dress shirt. What’s interesting that for a challenge that’s based on building a look around the same item we had two winners who tied in the voting poll that couldn’t be any more different!

2nd challenge v1


Edgy / Elegant – Edgy

Details to note:

This outfit is a great example of an image where the difference between edgy and elegant – edgy is a choice in colors because if we were to change the color of the leather jacket and shoes from white to black we’d have a pretty smooth elegant – edgy style.

But as the outfit stands right now, its loud, very attention grabbing and so cool it gives me the chills. This is an advanced look that I would not recommend to everyone due to it being very bold and hard to pull off, but if you’re among the people who can do that (and as far as I know the author of this look is one of those guys) you pretty much have your pick of women.

Now let’s talk about specifics.

First I’d like to draw your attention to contrast in styles between upper and lower body: in the bottom we have cool, edgy shoes and heavily damaged/repaired jeans, meanwhile as our focus moves upwards,  we find dress shirt, tie, watch and a fedora – quite classy items. It’s the jacket and bracelet that ties those two very different personalities together into a single image that has a lot of depth to it – a sort of party bad boy that can play a piano an recite his favorite poetry lines.

Best suited for:

In terms of when you rock it, the look is best suited for night game and maybe for some online dating photos.

As for physique, edgy looks generally look best on skinny/lean guys but because of the nature of the image (and if we’d look item-by-item) it’s actually quite forgiving and will look flattering on most physiques as long as you adjust the cuts.

That said, there is one major requirement for this look – it’s the personality. Here’s the deal, you pretty much need a personality of Russell Brand to really reap all the benefits from this look as it requires a combination of confidence, carefree spirit and raw, unapologetic sexuality.


Our second winner for 2nd challenge is almost the complete opposite of our first look.

2nd challenge v3


Elegant – Edgy

Details to note:

If the previous look was quite difficult to pin-point to where it actually falls in the spectrum between edgy and elegant – edgy, this outfit could be the poster style for elegant – edgy.

The outfit itself is quite minimalistic and how well it will work boils down to how good is the fit on your clothes.

Best suited for:

This is a very versatile look and generally as long you’re comfortable in semi-dressy outfits you can pull it off nearly anywhere, any time.

And a really cool thing about this look is that it’s just as versatile personality-wise as pretty much anyone can pull it off.

In terms of physique, it’s a great look for guys who are naturally handsome or have a physique of a Greek God and don’t want their outfit to overwhelm their features. The black vest & jeans combo also makes it a great look for shorter guys as the color palate in this outfit will visually lengthen your frame (though I would pick Chelsea boots over oxfords for another extra cm or two).

For really skinny and chubbier guys I would recommend adding at least one more layer for best results simply to help your shoulders look more developed.


The author of this look did not include the item details but none of the items are particularly rare and you should be able to find most of these on or another big online menswear retailer.

3rd Challenge: Colors Are Fun!

Even though the winning outfits where quite different in the second challenge, other submissions ended up looking rather similar, especially in our choices in colors so the third challenge was to test how good we are at playing around with colors – in other words, to create an outfit that has NO duplicate colors.

I must say that was one of the more difficult outfits I ever had to create!

And here’s our winner:

3rd challenge


Masculine – Rugged

Details to note:

You’d be surprised how difficult it can be to color coordinate when none of the colors can be used more than once in a look (great practice though!). In such situations you’re almost bound to stick with mostly neutral colors because any flashier color will eventually start clashing with other items.

And even when you do need to pick a color that’s not black, white, grey or brown, it’s best to stick with darker or lighter hues, so for example navy instead of blue, olive green instead of green (actually plain green is rarely a good color to wear anyway).

Best suited for:

The outfit can be a bit too casual and underdressed for most mainstream dance clubs or cocktail lounges but other than that it can work quite well in most situations, especially during the day time.

In terms of personality its just as versatile as the previous look and pretty much anyone not too bothered about looking casual can pull it off.

As for physique its actually one of the best looks for bigger guys as this style allows for slightly looser trousers. Shorter guys would benefit from choosing a thinner belt than the one shown in the example.


4th Challenge: Patterns Made Easy

Our fourth and last challenge to date was designed to address another topic that a lot guys find troublesome – use of patterns. The challenge was to create an outfit that has at least 2 different patterns (bonus points for 3 or more).

The winning submission went a bit crazy with challenge and used four different textures of varying intensities.

4th challenge


Elegant – Edgy (Sharp if we’d pick dress shoes over sneakers)

Details to note:

To truly understand this outfit we need to split it into two parts – sharp parts that consist of buttoned shirt, waistcoat, blazer, watch, dress trousers and playful / youthful parts – white sneakers, bead bracelet and white pocket square with small black skulls.

This way we can see how we can take an otherwise sharp, dressy outfit and make it more fun, exciting and cool. The overall result is that we have an image of someone, who knows the rules of men’s style and how to dress to impress but also doesn’t take himself too seriously and knows how to have fun too, without appearing tacky.

When it comes to patterns, note that they do adhere to the rules of layering as we’re moving from most intense pattern (shirts) to something noticeable but more subtle (waistcoat) to just few highlighting details that tie the look together (a touch of grey on the blazer’s lapels).

Pattern on trousers makes the look a bit less formal, less intense and in turn sets up the transition for the playful item – white sneakers (it would be much more difficult to pull off with stark black dress trousers).

Pocket square is one of those items that look classy and sharp from afar but when you realize that it has freaking skulls you just have to smile (and comment how cool it looks!)

Best suited for:

I’d say the look is perfect for fun bad boys who for one reason or the other need to dress up for a specific venue or event.

In terms of character you should be comfortable dressed up but at the same time maintain your cocky, playful vibe.

Lastly, physique.

In this area the look is extremely versatile and will look flattering on both skinny, muscular and chubbier guys. Dark colors and lack of color contrast around the belt line will also help shorter guys appear taller.


Finishing Thoughts

So, how did you enjoy these very special style inspirations?

Don’t be shy and share in the comments section what you liked, disliked or would change.

Spending some time consciously imagining and building such outfits is one of the best ways to develop and improve your own eye for clothing and style.

And as promised I would like to extent you an invitation to join our sexy group on Facebook. Now, it’s a secret group and you won’t just find it by doing a search (for privacy reasons and because I want to keep it a group of like-minded men, with a common goal of looking their best, sexiest selves), instead the only way to join it is to shoot me a quick e-mail answering two questions:

  • Why do you, personally, want to join our group – it doesn’t need to be anything elaborate, just honest and straightforward.
  • Where should I send you the invite, as in what e-mail address? You don’t need to include this if it’s the same e-mail you’re contacting me from. (Don’t worry, you won’t be subscribing to anything or whatever, this will only be used to send you a Facebook invite to join the group)

Afterwards, please give me about 24 hours to send the invite and later confirm you joining. I do this manually for the reasons explained above.

That’s it for today,

Happy Thanksgiving for those of you in the US (sorry, I’m a bit late on this for our Canadian readers 🙂 ) and for the rest, it might be a good time to take a moment and think of all the things you’re thankful for this year – it wasn’t that bad after all, wasn’t it?