How to Dress like a Cultured Hipster (Men)

Before you read this, make sure that you have read the 10 commandments of a cultured hipster’s style.

Casual Wear
A white button down shirt which complements your silhouette, either made out of fine woven cotton or linen would be recommended. But ensure that this is not a formal dress shirt. You can find out by looking at the collar – is it very taut and hard? If so, you’ve got the wrong shirt in your hands.

Match this untucked shirt with a pair of chinos perhaps. Navy would give you the most cultured feel. Also ensure that the pants are slim leg, and not straight leg (that would be too baggy in the opinion of the cultured hipster).Cuff the hems, and invest in a pair of white double strapped Birkenstocks.

If it’s slightly chilly, you could always opt for a burgundy crew-necked sweater or a beige trench coat.

To top it off, don a pair of round-ish sunglasses that give off an artsy feel (refer below to brands recommended) and carry a vintage camera in your hand (to carry it around your neck would be too touristy). Place yourself in a hipster suburb, hang around the contemporary art galleries and record stores and you’ll fit right in.

Brands to watch out for:
Clothing: Jac+Jack; Fred Perry; Scotch and Soda; Incu
Sunglasses: Oliver Peoples; Persol; Garrett Leight; Moscot

Smart-Casual Wear
Let’s get this straight. A two piece suit not always for formal occasions. And this depends on the cut and material. For a smart-casual occasion, a two piece navy suit would be recommended. Since it’s smart-casual, you can opt for a lighter navy or a royal blue. The fabric should be somewhat thick if you are going to have a two pieced suit, composed of something like a cotton poplin or a mix of linen and cotton. The reason as to why I am promoting the natural fibres is because they are breathable and last much longer that synthetic fibres. (fabrics such as silk, cashmere and wool are saved for the formal occasions.) The cut should be quite fitting against your body, accentuating your waist, and the pants should also be tapered and slim leg.

BEWARE: never ever wear a suit jacket and pants together of the same colour but of different material.  It makes the wearer look amateur and unkempt.

Now to the shirt. Since it is smart-casual, you can have a bit of fun with the shirt. A floral shirt is always nice, or something spotty. Express yourself! Or if you’re not wearing a suit jacket, get a bowtie! It’s fun, different and most importantly of all, looks good!

Also, wear a belt. It’s not required but it brings the outfit together nicely. With regards to socks, if you have printed shirt, match the socks to the shirt. Socks can be fun! Grab some spotty or stripey ones, or even some with rabbits on them. Try them out and see what suits you! And for shoes, to match a navy suit would be to wear a pair of brown shoes. The lighter the colour, the more casual you become. Also make sure that your shoes are not too bulky, because you must take into consideration your tapered pant leg. The proportions wouldn’t be right…

Brands to watch out for: Paul Smith; Tommy Hilfiger; Ralph Lauren; thrift shops (they usually have really good cheap two-piece suits).

Formal Wear
For formal wear, you must almost always have at least a two piece on, or even a three piece with a tie or bowtie. It is highly recommended that you get a suit custom-made so that you can choose whatever style, fabric and additional features that you would like.

For fabric, you can choose seasonal or all year round fabric. Some are made of wool, even for the summer fabrics, but don’t be put off by this because wool is a very warm material. High quality wool is wool that is not very dense, therefore providing the comfort and luxury of the material as well as being very breathable.

If you’re going to get a suit made, remember it takes time, so order and get a fitting ahead of time, and also if you are going to get one made that is pricey but good craftsmanship, I recommend that you get a more classic colour and style (once again navy is great). Talk to your tailor about this. The best cut would be a somewhat fitted jacket which gives a flattering silhouette, and slim leg pants, but not too tapered. A good tailor would be able to give you the right proportions.

With regards to the tie, ensure that the tie is not too thin. Thin ties make you look like a young boy. Choose something wider, but not too wide. If you use a bowtie, choose a conservative one, but with flair. For example, a forest green bowtie is already different to the conventional black bow ties. You can also match your socks with your bowtie. For shoes, choose dark coloured (preferably black) ones. If you’re going to choose a brown, ensure that it’s dark brown because this is a formal affair.

Remember, all of this is just a small guide. Always make sure that the clothing suits you and your character.Good Luck!

The 10 Commandments of a Cultured Hipster’s Style

1. Thou shalt never deny the cut. The cut is one of the most important parts of a piece of clothing. Clothing should complement your body, and give you a favourable silhouette. If it ticks neither of these two boxes, don’t even think about it. Even if the quality and the price is good, but the cut is horrible, it is not worth your time and money. You’ll just end up with buyer’s regret.

2. Thou shalt not deny quality. Quality, quality, quality. And if its all natural fibres (cotton, linen, bamboo) that’s even better. (But remember to still uphold 1))

3. Thou shalt dress for comfort, not looks. It’s not to say that looks are unimportant, however comfort is equally important. Those who dress for looks are only doing themselves a disservice. How could one still look good if they are uncomfortable?

4. Thou shalt have the essentials. And by essentials, I mean a white collared long-sleeved shirt, a classic white cotton t-shirt, a pair of comfortable and versatile jeans, a pair of dress shoes and casual shoes such as converse (vans are too mainstream nowadays.)

5. Thou shalt wear one item of clothing with flair. Indian-made natural-dyed scarf? Spotty socks? Colourful bag? Underwear with cats? The world is your oyster.

6. Thou shalt consider handmade/custom-made clothing. Handmade clothing gives a piece character. The item of clothing is tailored to your own desires – you can choose your own cloth, cut, stitching, whatever you like. It allows a cultured hipster to make a statement to the world about themselves and who they are.

7. Thou shalt never follow a trend (that’s too mainstream). Sure if you like a piece of clothing that is trendy at that time, buy it. But, if you have a good eye for fashion, you can also tell whether this trend will become a classic trend, or just a fad. If it’s still somewhat wearable in a few season’s time, wear it. And trust me, you’ll probably be even more stylish now.

8. Thou shalt iron your clothes. Trust me, even if you’re incredibly lazy, it’s not worth it. Especially for shirts. There is such a big difference between a non-ironed shirt, and an ironed shirt. (Then again, it depends how you want to present yourself…you may deliberately not iron your shirt. But if you want to be a cultured hipster, a cultured hipster would iron his/her shirt. Unless he/she was going for the casual and relaxed yet refined look. But that’s a matter for another day.)

9. Thou shalt value the importance of proportion. Proportion is closely linked to one’s silhouette, but proportion is slightly harder to manage. It’s hard to explain. Here are a few examples. Say you’re wearing a white shirt, untucked (ending around at the hips), with jeans and a beige jacket (which ends a third from the top of your thighs. This would violate the proportionality law because the length of the jacket is simply too close to the length of the shirt. The result of this would be a seemingly fatter upper body, or a very baggy upper body. A similar example would be wearing a very baggy top, with a very baggy pant. Don’t try this. Another example, do not wear a very long sleeveless top (cuts at mid-thigh) with baggyish pants and huge sneakers (this wouldn’t even be a cultured hipster’s style.) It just doesn’t work as it makes you shorter. (Justin Bieber does this quite often. Just google search him.) It’s not to say that all these examples look bad on everyone, but it is just very hard to execute well.

10. Thou shalt adopt a style which suits you. You should never suit the style. Once again, clothing is used to make you look better. It should only add to your character and the way that you want to present yourself.

Dress shabbily and they remember the dress; dress impeccably and they remember the woman [/man]. – Coco Chanel