When I was a kid/ teen, choosing some more or less good look has never been a problem (well, my parents were of some help too), but now that I'm in my mid-20's, I'm having a difficulty coming up with a way to dress well.

Just so you could get a picture about me, I'm into rock music (so hoodies, sports-team jackets, baggy pants, and all that jock stuff is not something I wear, ever). When I was 15-18, dressing in some torn jeans, a band t-shirt, maybe a denim vest, and combat boots was the go-to look for me. It didn't make me very attractive to most people, but the girls in the scene liked it, and I didn't need anything more. But as you grow up, you understand that the outrageous look isn't something you want (at least, if you're not a rock-star or something) - you're supposed to be an adult, and dress like it. So I've toned down my outfit: t-shirts, shirts, plain jeans, simple jackets, sneakers and shoes. No graphics (except for my old band t-shirts), no silly designs, or anything. Of course, colors and patterns didn't always match (if at all). But now, I want to actually dress well, to boost my confidence, to have people respect me, women to like me, to deliver the message about who I am, what my values and interests are, and all that good stuff. I keep reading all these books and articles (even on AoM), keep watching all these videos, try to follow, but I still end up looking like a has-been.

Trying to follow, I learned to somewhat match colors (I still try to keep my distance from patterns though). I also stopped wearing t-shirts, opting instead for polos and shirts; made a shift towards chinos instead of jeans (they're also more flexible), pay attention to clothing fitness (wearing clothes that fit me), and try to keep my hair in order. But something still seems way off, and I don't know what it is. Asking people is of little help - those that know me don't know/ care much about fashion/ style, and I'm not a sociable enough person to just ask the cashier at the store of their opinion on my look (that's just an example, but you get what I'm saying, I think). It's kind of a funny thing too: people here are closed-minded about the rock look and see it as immature, but wearing a tracksuit or pajama pants joggers in the street every day, or dressing like a stereotypical slut (if you're a woman) is absolutely fine.

Suits are also out of the question - way I see it, one only needs to wear a suit either if they're working in some serious organization, or if there's some special occasion (silly, I know, but bear with me), because wearing a suit everywhere all the time is just too much trouble.

So, what should I do? I can upload a few pics of my current outfit(s), if that'd be of any help, but I'll do that if anyone actually requests it.

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Many people don't know how to dress well and wish the did.  

Add a blazer into your rotation.  Corduroy perhaps but yes a blazer.  

Shoes, they should be leather and of a color you can polish and take care of.  I like Brogues as my go to shoe for almost everything.  They can go from suit to shorts no stress.
 

Sweat pants, Pjs, flip flops etc all have a place.  That place in specific places: the gym, house an hour before / after bedtime and the beach.

Fitting also is key.  If everything fits you are not a has bin you are looking classic and put together.

I end up getting my shirts from Brooks Bothers because I can order by the numbers and the cut and it looks good.  My pants and blazers, JC Pennies.  It is not about the cost it is about the fit.

I use my dress as a mood boost.  
For casual I go with Patagonia and LL Bean for my more relaxed look.  
 

I hope this helps.  It takes a while and you get boosts at odd points along the way.

Thanks for the reply. Blazers, I'm not sure about - I think they've never been a thing here, though I have seen them become slightly more popular in the recent years. About brogues - are they good for long distance\ everyday wear? Because I like walking a lot, and they say wearing shoes is bad for your feet and back, if you wear them too much.

Yes, I know about sweat-pants, pj's, flip-flops, etc. I just mentioned them because most people around me (where I live) seem not to :D


Fitting, yes, I'm paying more attention to it. Right now, I'm just trying to buy fitting clothes off the rack, but I am planning to employ the services of a tailor (once I do find one) - any suggestions on that, by the way?

The shoes need rotation.  One day worn the next they rest in shoe trees to reblock and reset.  After I broke in the leather sole I had Vibram soles put over them.  Its a synthetic sole that puts up with a lot of wear and tare.  I will admit it is an investment.  

You don't need a blazer as much as a structured collar to guide the eye to your face.  Polos and such also do this.  The key is to stay away from patterns and trendy things and keep with basic elegance.  Blazers provide a lot of structure to your appearance and are a go to thing for me. 

On fitting.  I go with brooks brothers slim fit shirts.  The shirts have 3 measurements.  Your neck size, arm length, and how tightly the trunk / body is fitted.  It works for me off the rack.  If suit shirt does not have 3 measurements, it probably will not work to make you look good.  I'm 6ft and that is about 1-2 inches short on a "medium" shirt.  But my chest is a "medium".  So I end up having to go higher end on my shirts to make them look good.

I was actually asking advice on how to find a good tailor :D


Telling me of brands is kind of a waste since: 1) I can't normally afford even the cheapest American\ European brands (1$ = ~20 lei - our local currency, and my salary is pathetic); 2) shipping will probably take months; 3) I don't really trust e-commerce. Still, the rest of the details could be useful.

I found mine at my church.  You might check out the theater groups and ask them.  I hate to say ask your elder ladies in your social group but grandma's and mom's have different networks then we do and know someone allot of the time.

Dressing well is context-specific.

Clothes that fit well is the first must.

Being adaptable based on context is the second, IMO.

I know guys who default to wearing a blazer and button-up shirt to everything because they figure that's what dressing nice / stylish means. But oversized blazers and outdated dress shirts don't cut it. And wearing a blazer anywhere/everywhere often makes them look out of place.

Dress in whatever feels comfortable and matches your style.  Don't worry about what other people think.

but what is my style?

Get clothing catalogs and cut out all the images you like.  This year's and 2 years ago are great.  You are not looking for the current trend but rather the overall look.

Cut the heads out of the image so you actually focus on the clothing.  Put that in a scrap book.

Label the pages "Work", "Going out", "Around the house", "Party","Camping" etc

Do this for about 2-3 weeks or as new catalogs show up.

Then review.  look at what keeps showing up.

What colors do you keep liking?

What outfits do you like?  

How do the pants Fit?  How does the shirts fit.?

I really helped me minimize my wardrobe and feel confident in what I wear.   

Add to that list a Charcoal Gray Suit, brown brogues and some shoe options and you will be set.  

check out the art of charm podcast/website.

being stylish is more about being confident then what you are wearing. So as long as you are comfortable and confident; ware anything. 

also see what your boss is wearing and dress similarly 

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