Venturing into the vintage style fashion as a man can be quite a daunting task. Vintage clothing in men stands out so much (usually not in a good way) that anything too flashy or out-of-place is instantly noticed. To help you, we came up with this list of casual outfit ideas for men, where we go through numerous ways you can incorporate casual – vintage or retro – apparel smoothly.
Forget about bad critiques and unflattering comments about your looks. With our suggestions, your casual outfits will be revitalized and you will feel way more comfortable in your clothes.
Note that images shown in this post are resembling the outfit at hand. We discuss these, as well as variations of them. At the end we present some suggestions for each case.
As a final note we focus entirely on XX century apparel and their vintage looking options from today.
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Everyday casual outfits – Simple but nice options
We start off by giving some suggestions on general everyday looks, that is for example, when you go out for a walk or to run some errands on a casual day. These outfits are simple but well arranged, so that you look fresh and comfortable at all moments.
The first outfit is a casual 60s one.
We go from bottom to top, so the first thing to note are the feet. Business casual shoes such as the Oxfords, the jam shoe, or even some moccasins are good choices.
The right choice for pants given the shoe selection would be slim fit. Try some intense flat colours on them, or if you feel like being more flashy, you can go for some square or linear patterns on them.
For the upper body, a polo shirt or short sleeve knit shirt works for warm weather, while the knick mock shirt and turtlenecks are better cold weather. Make sure to properly match the colours of all 3 sections
You can complement the outfit with a cloth bucket hat and/or a casual vintage watch (In our list of vintage watches for men you will surely find an adequate option).
Our second option for everyday casual outfit is a 90s throwback.
To start off we go for leather shoes. Some lace up boots or leather kickers will do the trick. Both brown and black are nice options, but remember you will have to match the rest of the colours.
For the lower body we had to go with jeans. Stick to jeans with older types of fabric and/or ripped jeans; these were very popular during the 90s, so go ahead and try them. See if rolling up the jeans matches with the ripping, if not, you can try normal ones and roll them up (Rolling up was huge in the 90s!). Also, if you wear a belt, match the colour with your boots/shoes.
Finally, for the upper body you have lots of options. In a hot environment you can wear a 90s themed T shirt (our T shirt post can help you with ideas) or a flannel shirt alone or combined with a T shirt. A cold environment can include a baggy jacket a crew neck sweater or baggy sweater.
Some options like the crew neck go well tucked into the pants. For the baggy style, maybe a cap will be a nice addition, otherwise, a necklace and/or watch never fails.
Summer Outfits – Look your best under hot weather
For our summer or hot weather outfits we will first go for a 70s look.
The feet work well with lost of casual shoes. Moccasins, sneakers, running shoes and sandals are ideal, while leather, boots, or platform shoes are definitely a no no. Some of these, like moccasins or sandals look better without socks, but using high socks with other options really accentuates the old-fashioned look.
For the legs shorts are ideal. All patterns and colours are OK, just make sure they reach above the knee and the colour goes well with the rest of the outfit. Striped and other patterns on shorts go well with flat coloured shirts.
As for shirts, we have that short sleeve or sleeveless works best. Polo shirts, T shirts, hawaiian-like shirts, and similar with a tight non-baggy fit is the way to go.
Accessories to complement the outfit are casual watches, short necklaces, and sunglasses.
Some nice options to shop this type of outfit are: Feet, Shorts, Shirt
Our next outfit is a little more modern variation of our previous summer outfit. This 80s look radiates a more masculine presence.
For this, sneakers or sandals are replaced by some work boots, moc toe boots, or similar.
High socks and the shorts remain the same, but this time around we go for a loosely fit dress shirt. The shirt goes tucked into the shorts (a nice thin belt will flash nicely but it is entirely optional), the sleeves are rolled above the elbows, and at least 2 or 3 of the top buttons unbuttoned (more is OK too). If you are well-built, this outfit will definitely go well with you.
Complementary accessories are hats (no caps), sunglasses, watches (casual and slightly formal), and long necklaces.
Bad Boy Outfits – Instant testosterone boost
If we go through some bad boy outfits you know we gotta talk about the original bad boy look. The 50s bad boy looked like this
So how exactly do you rock it properly?
Well, starting off with the feet, the classic bad boy wears some motorcycle boots, and if he is on a budget he goes for a standard pair of black and white high converse.
Dark jeans are ideal for the lower body, making sure they are standard fit or slightly baggy (not too much though) and definitely NOT skinny. Rolling up the jeans to showcase the boots/converse is a good idea.
You may already be aware of what the upper body looks like. The combination of white t shirt (on our T shirt post we go a little more in depth) and leather jacket is unmistakable. Make sure the leather jacket is at least a little baggy. Oh! and don’t forget the greasy hair and the cigarette on the ear 😉
Over the years this classic bad boy look has been modernized. By the end of the XX century the bad boy looked more like this
The converse were dropped and the boots got darker and tighter.
The same could be said about the jeans, which also started to be substituted by other high quality fabrics and ripped versions of these. A nice touch to add was (and still is) the chain falling to the pocket.
The leather jacket also got tighter and the white T shirt was replaced by black T shirts, stamped white T shirts, black turtlenecks, dark V-neck shirts, and even dark dress shirts.
The tattoos, chains, and sunglasses are huge bonuses when rocking this modern bad boy outfit.
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Party Outfits – Sharp looks for a night out
We finally get to our last vintage casual outfit section. The party outfits!
You probably have wondered how did men looked on a night out 100 years ago; well, we now present you with a casual way men used to go out and look really good. Although it may look slightly formal, its actually casual, so don’t go into a business meeting looking like this 😉
For the lower body you can start off by wearing either a pair of wing tips or some other semi-formal shoes. You can also try some short boots like the brogue boots.
The pants can be some dark slim jeans, if you wish to have a more modern look, or some suit pants or semi-formal trousers for a more traditional outfit.
On the upper body we have a rolled up (and slightly unbuttoned if you want) dress shirt. The final touch is some matching suspenders. To keep it casual, no ties, dress jackets or waistcoats are allowed.
Accessories are of course watches and hats, and remember to match the colours well!
So what’s a party outfit list without an 80s outfit?.
The shoes play an important role on this one. You can go for a conservative look with just some casual shoes like sneakers or boats, or you can go completely old school with some platform shoes. The latter ones are such a rare sight nowadays that you will surely stand out.
For the legs we have some skinny or super skinny plain jeans. The colour will be determined by the shirt and shoes.
The most important part is the shirt. An oversize printed shirt is the way to go. Flashy patterns and colours are welcomed as long as they match with the other pieces. Also, the shirt is tucked and unbuttoned (showing the lower chest or even beyond is acceptable).
With these clothes you can build a similar outfit: Boats, Skinny jeans, Oversize Shirt
A wide variety of options are out there to discover!
We hope that among all the different styles we covered, there was at least one that caught your attention. Remember that all of these outfits have dozens and dozens of variations that also look very cool.
Keep an open mind when trying this stuff and experiment a little with apparel you already have. You will be surprised of the combinations you can achieve!
Thank you for reading and we hope to hear from you in the comment section below.
Until next time!