Jan 13, 2017

Stepping Up My Style... Where to start?

Hello everyone,
A couple of weeks ago I came to the conclusion I need to step up my style. I'm a 25 year old web developer living in Europe and dressing casual every single day. This means, graphic tees, hoodies, zipped hoodies, sneakers, jeans (I do own a pair of Red Wing Iron Rangers, but that's about it).
I feel at this point in my life I want to dress more professional, not like a 18 year old anymore that just graduated college. I've been reading a ton of articles, watching a load of videos etc about Men's Style and I know the direction I want to go in. However, I can't afford to immediately spend € 1000+ on an entire new wardrobe and would like to gradually change my style.
My idea is to start at the feet, and get myself a nice pair of Chelsea boots, followed by all-white sneakers (maybe immediately, maybe a bit later). After that I'd like to invest in a good pair of dark-washed jeans and some well fitting chinos.
I'd love to hear some opinions on this 'game plan'.
- swain
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You don't need to suddenly dress up. Start with less rather than more - this applies to anything. I would suggest "muting" your wardrobe first (basic, versatile clothing). Also never buy things on impulse.
I think having some idea of what you like definitely helps. For me, I like a mix of style and practicality. I don't like babying clothes, I want clothes that I can wear every day and not worry about that also happen to look good. Good basics for this philosophy are chinos and oxford shirts. Nice and easy to wear, machine washable, and you look sharp.

Another tip I'd say is to spend a little more time and effort into shopping. I know that might not be everyone's cup of tea, but I find it truly beneficial to get it right. For me that means when I'm looking at something to buy, I try to think of at least 3 other outfits I already have that it can go with. If you keep doing this, eventually everything you have goes together and getting dressed in the morning becomes effortless. Then finally, spend time in nailing the fit. You can spend thousands on a suit, but if it doesn't fit you well, it's no different from an off the rack suit you can get in a mall.
Stick with the classics.
A black and a brown leather jacket. Belts , shoes, and boots that match the leather jackets. Clarks desert boot bees wax. Match socks to shoe or pant. Flat front slim chinos. Raw selvidge denim. A nice watch. Nice wallet. Some nice buuton down shirts, but not to many prints. Plaid is over done. I also wouldn't go too bright in colors, except for a nice royal blue. Some corduroy is nice. Keep it simple.
There's alot of fasion advice on you-tube.
Whatever you do don't go for a generic look or blindly follow style forum group think.
Build a wardrobe that has garments appropriate for what you need to do.

Your Jeans ....Tees and hoodies are versatile and comfortable and grayman.
I'm old and never wear pants.
Heck. I just bought my first pair of denim on MassDrop.
I don't even own a single dress shoe.
Matter of fact, I'm typically barefoot.
I wear a T and shorts to interviews.
My beard is never shaved.
My hair is a middle of the road Mohawk.
And I don't care.
Because when I show up, people smile or laugh. And that's good enough for me. Its worked this long.

Do you dude. If you think you need a change in attire. Do it. Try stuff. I am. Can't wait to own denim that I'll probably end up never wearing. :D that's the point. Have fun. Be easy. Good luck.
I would recommend not buying a ton of stuff immediately. Gradualism is huge when it comes to clothes. When I was younger I bought a lot of stuff I ended up never wearing. Still, that's part of the learning process.

I would view it as an experiment where you're constantly trying small new things and analyzing the result.

That said, you're talking about "investing" in dark jeans like, several steps down the road . . I think if you're wearing a t-shirt and jeans every day you can move faster than that.

Personally I don't like Chelsea boots but to each his own. I recommend upgrading from a t-shirt first . . . t-shirts are really underwear. That's how they began.

I recommend getting a collared shirt. The most versatile thing I own is a blue oxford button-down. I have three of them, actually, and wear them out and replace them all the time. You can wear it with jeans, with chinos, with sneakers, with nicer shoes, etc. You can roll up the sleeves in hot weather. You can put a sweater over it in cold weather. It's an all-season item. J. Crew's slim regular-weight oxford is great.

I don't really recommend getting a blazer unless one is appropriate at your workplace. I think blazer says "try-hard," unfortunately. There's just not a lot of call for it in everyday life. There are probably people making it work. You should probably work your way up to that though.

So I say start there and you can still wear your jeans and sneakers, etc., but then upgrade from there. I don't see how Chelsea boots would work with the other stuff you're wearing right now, whereas a nice button-down would.
A couple things I'd say:

(1) "Professional" is relative. I work in tech in San Francisco, if you wore a blazer to work everyday you'd definitely be "That Guy". Maybe you're comfortable with or even relish being "That Guy", but you should be aware of the choice you're making.

(2) Resources like Male Fashion Advice on Reddit are great for inspiration and education, but do tend to fall into a bit of group think. If you want to develop your own aesthetic, you're going to need to experiment. I found second-hand thrift shops great for doing this with minimal cost. I tried a bunch of looks, I ultimately found out I looked a combination of super casual (well-fitted graphic tees, jeans, casual kicks), rugged-ish (work boots, chambray/denim work shirts), and formal (dark colored suits with traditional styling) worked best for me. Preppy, not so much. I also found out I really don't give a damn about selvedge and raw denim, but I did care a lot about suit construction and shoe stitching. But it took me a lot of trial and error to get there.
Lose the hoodies and get yourself a blazer. That should be step one that works even with sneakers and even (dark-topped) keds. Forget about white sneakers. Chinos and Chelsea boots should be step 2.
You're gonna have to define what "professional" means to you, and tell us more about your professional/social context. If you're a web developer and don't have a lot of face-time with clients, for example, then wearing a suit to work will make you seem out of place.

Don't spend a lot of money to start, you'll end up with a lot expensive mistakes. In the sort term, you can swap out your graphic tees for plain tees in white, grey, navy, burgundy. You can swap out hoodies for a nice light jacket, maybe something in the Harrington style. Don't wear pre-distress jeans, go with a pair of dark denim. There's currently a drop for the MDxAE chukka, get on that. Start small and build on it slowly.
Hi Swain, nice to meet you, I'm Muni 33 years old, living in China, I graduated fine art school in London many years ago, self style is a long way you need take, but the real mission is finding youself. When college time, I only wear Bape (Japanese Hip-Hop style), lot's of camo graphic, loose fit hoodie, jeans, sneakers... Many years later I still wear hoodies, sneakers, but going black white grey, going tight. Now I am a father, jogger pants, NMD I wear everyday, I just wanna tell you, don't let situation changing you, evo your styles by youself...
Unless you job demands it, I'd start with the opposite end of your body, which is your top. A nice blazer (especially with a pocket square) can quickly "formalize" any tee and jeans casual look. Throw in a polo or plain/gingham shirt to replace the tee and it will add more formal look.

From there you can add a tie (if you're wearing a shirt) and replace your sneakers with a leather shoe. Unless all you have are ripped jeans, it would be last piece I'd change. Most often than not, nowadays a lot of workplace have started to accept more semi-formal wear unless your job is strictly client facing.
arislan
Good advice. Id like to add that the fit of the pants would be important as well to give balance to your whole figure. Of course it depends on your body shape but if you are kinda more on the slim side, go for slim fits, it will draw more attention to your shoes too. For starters, you could try to get one off-shelf, great brands such as Uniqlo offer free tapering. Then later one, have them tailored to your specific fit.
I think the move from boy's clothes to man's clothes needs to be faster and bolder. At this point it doesn't help you just to buy more expensive casual stuff. You're ready for shoes that are NOT sneakers, pants that are NOT jeans, and a jacket you can wear with a tie.

The other suggestions people have given are a good path to follow--get some clothes you can wear in a professional office setting like a sport coat, dress shirt, (slim) chinos, and oxfords. In Europe you can use Massimo Dutti as a starting point--their dressy stuff is low quality, but at least it mimics a quality look.

I think Chelsea boots are a joke--really, elastic boots??--but I may be alone on that.
Depends on what you mean when you say "Professional"

You typically have two avenues in Menswear; Classic Menswear ( Suits, Sportcoats, Shoes, Shirts, etc) and Streetwear ( Tees, Sneakers, Denim, Casual Wear)

They can intertwine as people mix sportcoats with denim and boots, but when you say professional, I assume you are referring to the former?

If that is the case, I think a Navy blazer is always a good versatile piece to own. Try to stay away from the trendy items with skinny lapels. Make sure the shoulders fit well. If you want something really versatile, try something unstructured with no lining, as you can layer the jacket with other items and go from the office to the bar.

Also a nice charcoal grey suit is another staple piece. A white poplin cotton dress shirt, a blue oxford cloth dress shirt are always staple colors/fabrics. A navy grenadine tie or silk knit tie is also a good piece that doesn't look too formal. Make sure your suit/ sportcoat has some sort of horsehair canvas and is not fused. If you can pull the layers of fabric apart, it is not fused, which is a good sign. A fused suit is usually stiff and will end up forming bubbles over the years.

Pocket squares- you can never go wrong with solid linen, or you could always do something in a fun print to throw in your jacket even if you don't wear a tie. These can be 100% silk, Wool/Silk blends, or cotton. Go for the ones with rolled edges.

A solid pair of brown/ tan cotton trousers are also a good start- typically in cotton canvas or cotton twill.

For shoes- I started out with a pair of tan semi-brogue oxfords, which I wore with suits and denim. You can also never go wrong with a pair of chocolate suede chukka boots ( something I prefer over the chelsea and is a classic, my first pair were from Crockett & Jones) You can find cheaper variants but i've had my C&J's for almost 10 years and they look beautiful.

My advice is its better to spend the money on a few good classic items, rather than purchase cheaper clothes that you'll end up getting rid of because they are trendy or fall apart, and end up having to spend more money in the long run anyway.

hope this helps. best of luck!
If need be, (and if you are in a larger area), there might be a second hand gentleman's store that sells quality used bespoke suits and the like.
Button down one color shirts. Get them altered/tailored. Pair of khakis and slacks too. Its a start.
Sounds like a pretty good plan! I'm definitely no men's style expert, but getting a good pair of raw denim that you can start breaking in/wearing daily is also a good next step. Some dark denim can really spiff up a look (in my opinion) and you can really style them up or down. Cheers and good luck!
Tyler
What's makes raw denim better than, for example a pair of Levi's (dark washed)?
iamswain
I don't have a ton of experience with Levi's dark washed jeans, but I know that I prefer the weight, quality, and overall feel of a pair of raw denim to the Levis I own. If you like cuffing, raw denim is also generally easier to achieve that clean fold. It's also just fun to go through that process of wearing daily/breaking in!
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