Playboy Style: 1 Classic Summer Outfit

When it comes to summer style, less is more and this classic staple of my wardrobe is my top outfit to rock when I’m not suited up. It’s dressy enough to hit the bars with, but casual enough to rock when riding your motorcycle. If you’ve been struggling to find a good summer outfit, then look no further. This is one classic summer outfit that is timeless and will have you looking great.


A classic v-neck stretch fitted t-shirt. You can wear any color that looks good on you, because the rest of the outfit’s colors will match any color you wear for the shirt.

While there’s a million brands to choose from, H&M makes solid T’s that are cheaper than your average lunch and have solid durability.


This one is less than $10 and can be bought here: H&M V-Neck T-Shirt


Nothing beats a good pair of jeans and while we all have our favorite brands, here’s some of my picks. The key is to get them in dark denim. Dark denim is ‘dressy’ enough to get you into bars, but rugged enough to look good on your bike, or even on a date. I always opt for the classic straight leg style (NOT skinny jeans. I can’t fit my cock n balls in those bitches).

Abercrombie makes a great pair of jeans (I’ve had some pairs for over 5 years) and these bad boys are on sale right now for only $30 (normally $78). It’s an online sale only, so get em while you can here: A&F Men’s Classic Straight Leg Jeans

Note: I’m not getting commission on any of these brands, just spreading the word.



It doesn’t get any more masculine then a good pair of boots. I have many styles ranging from cowboy to motorcycle style, but here’s a pair that are comfortable, inexpensive and look great. I have yet to wear these bad boys out and not gotten opened by a girl for the unique style. The brand is Call It Spring (the online selection is bad, but usually they have a great selection in the actual stores) and I copped em for around $140. You get an idea of the style of boots though and combined with this outfit you have a great summer look that’s cheap, looks good and is classic as it gets.

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I can’t find these online anymore, but here’s a picture of my very own personal pair.

Check your local Aldo for solid boots, or even hit up some vintage or thrift stores. That’s usually where I get my cowboy boots.


Pair up this outfit with a simple bracelet to give an extra edge to your look. You can find these suckers for hella cheap at H&M, or even thrift stores.

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This one pictured is less than $10 at H&M. H&M Black Bracelet.

The great thing about this outfit is the more you wear it the more it looks good. The jeans break into your body mold, the boots look even better beat up (I actually scraped mine with some rocks before wearing them) and the t-shirts are always better after a few washes.

How To Wear It

There’s 2 different ways to wear this outfit and I do both based on my mood and the setting.

Either tucked INTO the boots (left), or regular style OVER the boots (right).


Need help with style? Get the guide for men’s style here.

Read More: The Casual Playboy Outfit

16 Replies to “Playboy Style: 1 Classic Summer Outfit”

  1. Wait, this is just a t-shirt and some jeans? Lol, the boots make the outfit though. Women apparently notice and appreciate your shoes, so you’ll stand out amongst all the Vans and Nikes!


  2. This must be region specific. I live in the southeast and I would get laughed out of the bar wearing anything like this outfit.


    1. Wearing a t-shirt, jeans and boots would get you laughed out of a bar in the southeast?

      What do they wear there, because this outfit works in any bar from Indiana to New Orleans to Los Angeles as I’ve rocked it in those respective cities and wasn’t the only one dressed like that.


      1. Looks good to me. It’s as dressy as most anyone else in the bars here in KY. My only quibble is the bracelet, it seems a little effeminate. A nice watch would be a better accessory for my personal style.

        Keep up the good work!


      2. The higher tier bars around here are more prep. Colored button downs/collared shirts, khakis, loafers. I’ve seen people get turned back at the door for t-shirts. Might be able to get away with this at college bars but the girls wouldn’t be into it. Just my experience.

        Liked by 1 person

      3. McQueen-the South isnt worth a thought-so who cares what they think? Home of Skoal, Jim Crow laws, Country music, etc.

        The more time I spend in Murica’ the more I believe what Roosh says about location.


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