So I heard you like a challenge, fellow Joes? The thought of making it happen with a pretty woman you just met on the train, coffee shop, or simply walking on the street makes those pants feel even tighter?

Well, if that’s the case you have my utmost respect and I might as well do my part and help you prepare combat gear to make sure you have a proper fighting chance.

How To Dress Sexy For Day Game?

Different from the Style Inspirations we discussed previously, during the day you don’t have the warm embrace of social familiarity that you get in college or work place, you don’t even get the social acceptance of being overly sexual that comes with the night.

Instead, you have a bunch of people running around, doing busy work and barely noticing that life is happening around them.

So why would one want to do this?

Well, first off, it gives you the opportunity to meet the beautiful women, who are otherwise not on the market. Yes, some people don’t have Tinder, dating profiles and don’t like to get wasted at nights – I know, weirdos, man!

Secondly, it’s your privilege and your DUTY as a sexy man to brighten the day of some pretty lady, who’s just going around her day and has no idea, she’s about to be swept off her feet by an amazing guy that is you.

Unfortunately, because of the mundane reality of day-to-day life, not every women is going to be all cheerful and excited about meeting you, at least before she gets the chance to know you.

So what we need is to help you, urban Casanova, create an image that will instantly (and correctly) identify you as the smoothest bastard in town, Sex God reincarnate himself, with class and social grace that would make Barney Stinson look like a shy awkward guy in comparison (and how do you stay so humble too?!)

To do this, our style needs to achieve the following:

  • Show that you’re not a social risk to be seen with in public (sorry pink hair, we’ll leave you for some “Rave Style Inspiration”)
  • Differentiate yourself from the crowd.
  • Display yourself in the most flattering light.
  • Show that you get to sit at the cool kids table.
  • Create an easily identifiable persona.

Let’s get going then!

Casual Badass

Even real badasses need a break – all those one against ten fights, blowing up buildings, jumping off burning motorcycles 50 ft in the air and hitting enemy helicopters, sleeping with your nemesis‘ wife, you know, busy work, can get quite tiresome.
And so, when on Monday afternoon, after saving the world (again!), you‘re chilling at the coffee shop and you see a cute woman enter, you don‘t really want to try hard to impress her and instead just make it perfectly clear – I‘m bad, you‘re bad and we will do bad things together in my hotel room.

Casual Badass

  • Leather jacket – Brown leather jacket, clean but masculine. I’d avoid biker jacket for this particular look but any other design will work. You can even pick a coated leather jacket if it’s already getting cold.
  • Buttoned shirt – White, clean dress shirt. Fit can be a bit relaxed in fit if you’re on the bigger side. Can be worn both: tucked and untucked (more casual, laidback option). At least two top buttons open.
  • Jeans – Blue (ideally dark blue), blasted or with medium or heavy wash. Can even be distressed – it‘s a badass look, remember?
  • Boots – No good badass look is complete without a kickass pair of boots. I especially love this particular example because it also has some black highlights, which slightly breaks the all brown combo and also enables us to pull off black bag with extra style points. Match with jacket.
  • Belt – Brown, thick leather belt. Ideally, rugged. If you don‘t have a great option, better just wear shirt untucked.
  • (Optional) Sunglasses – If it’s still sunny in Autumn where you live, feel free to add a pair of aviators to the look.
  • (Optional) Bag – First off, if you don‘t need a bag, that‘s perfectly fine and just ignore it (please don‘t start carrying a bag just for the sake of having it, that‘s very tryhard). We want to go with a black leather option to maintain the masculine vibe and also introduce another color for differentiation.

Best suited for: Boots are great for shorter and taller guys alike. This outfit can be pulled off on most physiques, just make sure the fit on shirt and jeans is spot on.

Cliche pick up line to use with this look: Hey there, do you feel like saving the world tonight?

So Cool It Hurts

It‘s like in the commercials: you pass and women seem not to have control over their hands anymore, bras are unhooking and panties are, literally, dropping.
That‘s not AXE effect, not at all, that stuff is for amateurs and you play in the big leagues now.

So Cool It Hurts

  • Leather jacket – Distressed leather jacket, if it looks worn out that‘s perfectly fine (actually even better when combined with the rest of the look)
  • Flannel shirt in plaid – The item that takes a simple, good attractive look and gives it character (and extra warmth). Worn unbuttoned. Avoid very bold, attention grabbing colors.
  • White V-neck – Simple, plain, white V-neck (can be scoop neck too). Don‘t overthing this part.
  • Jeans – Dark blue, slightly washed look. Should be quite tight so you might need to pick skinny fit (slim is fine too). Skinny cuts can be either rolled up or tucked in, slim cuts rolled up.
  • Boots – Badass combat boots, rugged and black. That is all.
  • Necklace – Long chain (should reach your chest), it‘s should be a subtle detail (avoid really big pendants) that takes the look to the next level and not the main attention grabbing item.
  • Stuble – not exactly something you can order from Asos, but a short stubble would definetely help this look as otherwise you‘re slightly at risk looking too „teenage‘y“ (okay if you‘re in your early 20s).However, avoid full beard with this look or you just might find yourself spending days in a queue waiting for a random Apple product.

Best suited for: Fit and lean or skinny.

Cliche pick up line to use with this look: (Look in to her eyes, slowly and subtly smile) Hi… (pause while maintaining that captivating eye contact, give her your hand) Come… (and she cums)

Urban Gentleman

Who said romance is dead? It‘s very much alive for you!

You give a rose to stranger waiting at the bus stop and walk away without saying a word, just that all-knowing smile. All that just to brighten her day and even though she never knew you, she‘ll never forget you either.
You never worry about those who got away, you‘re too smooth for that, especially when your phone is blowing up from all the women, who want to invite you „for tea“.

Urban Gentleman

  • Blazer – Grey, slim cut blazer. Otherwise classic design. Avoid any designs or other unnecessery details.
  • Butoned shirt – Pink is a great color for this look. For the example I chose one in check. Clean designs would also look great but a bit more classy and less casual.
  • Cardigan (waistcoat) – Black tight cardigan or vest. Deep cut with either option.
  • Jeans – Mostly clean, slim fit blue jeans. Slight wash is okay too and makes the look more casual.
  • Boots – Brown smart boots. Design should slightly remind something you‘d see on a pair of oxfords. Avoid rugged designs.
  • Pocket square – Match with shirt, worn informally. Pocket square in casual situations is a bold move and if it makes you uncomfortable, you can tone down the outfit by skipping on the pocket square (you pussy!)

I‘d like to note, that this is quite an advanced look based on color-coordination. We‘re using multiple „main“ colors to avoid appearing serious and intense. Instead, this combination appears very light-hearted, fun, effortless (yes, the irony) and also very stylish.

Best suited for: Can be pulled off by most sizes. Shorter guys, better stick with monochromatic shades, get shoes with a sizable heel.

Cliche pick up line to use with this look: Careful what you dream off, because here I am and yes, this rose is for you.

He‘s A Pro

Let‘s say a big Thank You to Thomas for this inspiration!

You‘re a professional – both, the boardroom and the bedroom, and you don‘t shy away from making your image reflect it.
That slick confidence is what makes you so damn irresistible, that and your dress shoes. So you‘re not surprised when she asks you to keep them on while she‘s on her knees in front of you later that evening.

He's a Pro

  • Smart trousers – Slim cut, can be low rise waist. Grey would be the best option for this look.
  • Dress shirt – Clean, white dress shirt. Pink, teal are also valid options. Worn with two top buttons open and (if without coat) sleeves rolled up.
  • Shoes – Black, clean dress shoes. Avoid shinny look though.
  • Belt – Black, clean leather belt. This is a classy look so make sure the belt is well maintained too.
  • Watch – We‘re going for a smart look here so a simple, slick watch is the best accessory. Avoid pieces that have a lot of details and grab all the focus.
  • Coat – Black, clean, slim fit coat. Longer for tall guys and shorter (should end just bellow your belt line) for shorter guys. By the way, I actually awed when I found this particular example. Anyone wants to order me size M?
  • Scarf – All hail color! A common mistake with such “shades of black” slick looks is that they look too serious, almost boring. By adding a colorful scarf we grab attention, differentiate ourselves from the crowd and show that we know how to have fun. Red is another great option, but it would look much more intense.

Best suited for: Can be pulled off by most sizes, however, guys with a less than impressive waist avoid keeping dress shirt as top layer, add a vest or a blazer. Shorter guys, better stick with monochromatic shades, look for dress shoes with a heel and pick a shorter coat.

Cliche pick up line to use with this look: Excuse me, when‘s the last time you‘ve done it on an office table?

Finishing Thoughts

To finish off,

Standard 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? 🙂

And that’s it guys, now you have my blessing to hit the streets and make some pretty ladies very happy!

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