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What makes a good tailor?

geg_gee

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I'll start off by saying that I am, in all respects, almost a perfect innocent when it comes to the world of fashion, textiles, etc. As a no-longer-young adult approaching middle age more rapidly than I'd care to acknowledge, though, I'm entering professional settings where band t-shirts and Levi's are no longer the endearing, unceremonious garb of a carefree youth, but more like large neon signs advertising me as an overgrown child. At the same time, I dread lapsing into a soulless business-casual uniform that would by all means be totally appropriate to my current station in life. As a result, I have started to take more of an interest in the clothes I wear, and to make an effort to look somewhat presentable, even if I am not always successful. Although money is tight right now as I move to a new job (about which I am quite excited, thankfully) I am trying to learn what I can about clothing in order to improve my sartorial sense and presentation, in the hopes that soon I will be able to look moderately less like a total schlub and more like someone who has his wardrobe - and maybe even his life - well put together.

Although I'm originally from a city that has a reputation for being quite fashionable, no expertise in this domain ever rubbed off on me, and I now find myself in an area where retailers are somewhat more limited. This may be a good thing, as I would almost certainly be overwhelmed if my options were any more expansive (I am effectively overwhelmed now, as evidenced by my need to post this). However, I also find myself in an awkward position of having only a few menswear shops available locally, and being unable to judge their quality or pricing accurately. There are some boutiques that offer more streetwear items, but I don't think this is what I need in my life right now. A popular tailor down the street has very reasonable prices, but I get the sense that he's more of a no-nonsense hemmer of pants and sewer-on of buttons than someone who is into fashion trends. I took some off-the-rack shirts in to ask if he could suggest any alterations, and he shrugged and said, "looks good." Perhaps they do, but I was suspicious and expecting a little more feedback.

There's another shop downtown that sells clothing that's a little pricier than what I was used to buying in my younger days (e.g., $200+ pants, nothing exceptionally high-end), and has a very welcoming and seemingly knowledgeable owner who fits the clothes he sells. At the same time, given my total ignorance in the field, I can't actually tell if his prices are reasonable or if his skills are impressive - maybe I would be better off just ordering online and taking them into a less expensive place for tailoring. He's a friendly guy, the store is in a nice part of town, and I'm happy with the clothes I got from him, but I'm also wary of being taken for a bit of a ride. My gut instinct now is that this place is actually fine for my current needs, and that I probably wouldn't know to appreciate something better even if it spit in my face, but that it may also be a bit overpriced for what it is. I'd be willing to drive a fair distance to other locations in my region for someone else to compare, but again, I don't really have a good idea of what to look for.

This is my very long-winded way of turning to you, oh unimpeachable internet denizens, and begging your advice: what should one look for in a tailor? Or, perhaps even more importantly: what should one look out for? Any feedback or guidance is much appreciated.
 

breakaway01

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After all of this I am still unclear on what you are looking for.
1. Do you have a sense of what kind(s) of aesthetic you are going for? You said that you are not that interested in streetwear. What about tailored clothing?
2. What are you expecting from a tailor? Someone who can make clothing for you (that's not the sense I get)? Or someone who will advise you on clothing choices? Why does it have to be a tailor (someone with expertise in making and/or altering clothing)?
3. Where do you live? You might get more concrete recommendations about places to check out. If you are willing to name the shop, even better.
4. Would you be willing to post pictures of you wearing clothes you bought from your current shop? If so, you might get useful feedback on whether you're getting good advice and fitting from this person. Otherwise it's impossible for anyone here to tell you whether to stick with this person or move on.
 

geg_gee

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Thanks for your response, I appreciate your clarifying what I should be thinking about. Addressing your points:

1. I'm still trying to develop a sense of what I'd like to look like, what actually looks good on me, and what to search for in order to learn more. I said I'm not interested in streetwear, but maybe that's not quite right. From my teenage years, when I think of streetwear I think of sneakers and hoodies, but a suit or sports jacket would be overkill for the work environment I'm moving to. It sounds silly but, now that I think about it, Mr. Rogers or Bill Cosby is probably about the level of dress that would be appropriate.

2. I guess I figured that a tailor would be able to make alterations, have a good sense of what was in style, and be able to point me towards items I might consider adding to my wardrobe. It would be nice to have clothes made eventually, once I have a better sense of what I want, but that's not necessarily what I'm looking for.

3. I live in the Western part of North Carolina, but will be spending most of my week in the Raleigh-Durham area once I start working, and can stop in Charlotte pretty easily on the way between. I'd link the store, but I don't think they have a website (!?).

4. With some trepidation, I've attached a photo of myself wearing the pants I bought from the store. Criticism is very much welcome, but please, no tomato throwing. I'm doing my best.

my pants.jpg
 

breakaway01

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I think those trousers look good on you. I like that they are not skinny and are proportional to your build. Personally I'd hem the trousers a bit so they don't break quite so much.

As far as finding your own style, spend some time here lurking and looking at pictures. The various WAYWT (What Are You Wearing Today) threads in both the Classic Menswear and the Streetwear and Denim sides are a good place to start to get some ideas.

If you haven't already seen these, I'd suggest you look here and here to start off. I think these guides provide generally good advice to people just starting out. I can't emphasize enough the importance of starting slowly. Your taste and sense of what is most flattering for your body and style will definitely change over the next few years.

I don't know anything about clothing stores in NC but hopefully others here can provide recommendations.
 
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Crispyj

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Thanks for your response, I appreciate your clarifying what I should be thinking about. Addressing your points:

1. I'm still trying to develop a sense of what I'd like to look like, what actually looks good on me, and what to search for in order to learn more. I said I'm not interested in streetwear, but maybe that's not quite right. From my teenage years, when I think of streetwear I think of sneakers and hoodies, but a suit or sports jacket would be overkill for the work environment I'm moving to. It sounds silly but, now that I think about it, Mr. Rogers or Bill Cosby is probably about the level of dress that would be appropriate.

2. I guess I figured that a tailor would be able to make alterations, have a good sense of what was in style, and be able to point me towards items I might consider adding to my wardrobe. It would be nice to have clothes made eventually, once I have a better sense of what I want, but that's not necessarily what I'm looking for.

3. I live in the Western part of North Carolina, but will be spending most of my week in the Raleigh-Durham area once I start working, and can stop in Charlotte pretty easily on the way between. I'd link the store, but I don't think they have a website (!?).

4. With some trepidation, I've attached a photo of myself wearing the pants I bought from the store. Criticism is very much welcome, but please, no tomato throwing. I'm doing my best.

View attachment 1816508


1. Can try stores like Division Road. They have very high quality brands and they all work well with each other.

2. Most tailors do not have a good sense of style, even for bespoke tailors. And even if they are good tailors with taste, they wouldn't work on alterations.
 

geg_gee

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Thank you all for the advice. Based on your comment regarding tailors, am I to take it that I effectively need to figure out exactly what I want and then go in and tell them that? It sounds as if "good tailors with taste" really just make bespoke clothing (understandable) and that others need to be told precisely what you want them to do (also understandable, but requires me to know what the hell I want in the first place). Am I off base?
 

Crispyj

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Thank you all for the advice. Based on your comment regarding tailors, am I to take it that I effectively need to figure out exactly what I want and then go in and tell them that? It sounds as if "good tailors with taste" really just make bespoke clothing (understandable) and that others need to be told precisely what you want them to do (also understandable, but requires me to know what the hell I want in the first place). Am I off base?
Yea, but you're better off trying RTW brands than customizing everything through trial and error. It's a lot cheaper, trust me.
 

breakaway01

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Thank you all for the advice. Based on your comment regarding tailors, am I to take it that I effectively need to figure out exactly what I want and then go in and tell them that? It sounds as if "good tailors with taste" really just make bespoke clothing (understandable) and that others need to be told precisely what you want them to do (also understandable, but requires me to know what the hell I want in the first place). Am I off base?
In general my experience has been that alterations tailors aren’t going to advise you on how to dress. Their customers have very different style preferences, and I think alterations tailors generally don’t want to state their opinions on your style choices, perhaps because that wouldn’t be good business.

On the other hand, you should expect a good tailor to advise you on to get a particular garment to fit better on you. You shouldn’t have to tell them how to accomplish that. For example, if your jacket has to be taken in, you shouldn’t have to tell them at what seams and by how much. You may find that their preferences differ from yours (height of trouser cuffs or amount of trouser break) and you might have to tell them what you want for those kinds of things.
 

geg_gee

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Yea, but you're better off trying RTW brands than customizing everything through trial and error. It's a lot cheaper, trust me.

Sorry for the late response, but I've been thinking about this for a few days and wondering exactly how it should be interpreted. Should I simply not bother having off-the-rack items altered, and try to find things that fit well in the first place? Or is it inevitable that some things may need to be modified, but I should avoid having clothes made for me for a long while?
 

Crispyj

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Sorry for the late response, but I've been thinking about this for a few days and wondering exactly how it should be interpreted. Should I simply not bother having off-the-rack items altered, and try to find things that fit well in the first place? Or is it inevitable that some things may need to be modified, but I should avoid having clothes made for me for a long while?
Simple alterations are fine, stuff like length adjustments, width. Of course fitting without adjustments will save you quite a bit in the long run. Once you know what you like, then go get stuff made.
 

TheIronDandy

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Like some people have stated, don't expect a tailor to give you too much useful advice on how to dress. Even the high end British and Italian tailoring houses employ tailors and cutters, not designers or stylists. If you go to most bespole tailors, they will give you the "house style" because that's what they're good at. At best, they might politely suggest that "Sir may be better served visiting <other tailor or store>" if they think your ideas are not in line with what they do.

Alteration tailors are generally the same - they know TAILORING (to a greater or lesser degree), not styling. Having opinions is not a strong indicator of knowledge (and many people with few clues have very strong opinions indeed!) Many will also be influences by the type of work they do - if they adjust a lot of short. slim fit fashion suits that's the kind of look they will give you, regardless of if it's a good look for you. The same thing applies to many sales associates (especially at larger chains); they are simply trained to push whatever is in style right now, which generally means too slim, too short trousers and shirts.

I would suggest you check out dieworkwear.com, putthison.com (Derek, who runs dieworkwear, writes for both of these - he's also a frequent poster on this site, and highly knowledgable but with a black belt in snarkery) and permanetstyle.com Do some searching on those sites for casual/business casual wardrobe, and see what styles speak to you. Permanent Style is UK based and covers more high-end/bespoke products (the trick is to consider it INSPIRATION, rather than purchasing advice), DWW and PTO are US based and cover a wider variety of brands and price points. Permanent style has a pretty good introduction to various approaches to casual style, which might also serve as some inspiration.

For what it's worth, I was recently asked by a friend who, in his mid 40s and with a solid career, was realising that the way he dressed was making it harder for him to get taken seriously by senior management, how he could up his business dress without looking like a dork or a suit. My basic advice was to get some high quality classic chinos (I recommended Rubato) and jeans (Berg&Berg). These are hard wearing, good quality and have a classic, more relaxed fit. Then get some MtM shirts: I use Shirtonomy for mine. Then some casual leather or suede shoes: Loake is good, and Skoaktiebolaget has their own line of shoes called Lööf&Tung which are good value for the money. Keep in mind, all these brands are local (I live in Sweden), so importing to the US might be more of a hassle, but I'm certain someone around here can suggest similar brands or stores which carry some of these brands in the US.

Essentially chinos, quality jeans, shirts (often oxfort cloth button down, or OCBD as it's usually shortened to), and casual leather shoes gives you a platform to work from. You can add knitwear (I'm personally a big fan of Luca Faloni cashmere), outwear or sport coats as suitable for the weather and the level of formality you are going for.

Note that nothing I suggest here is cheap; the jeans and chinos are around 300 (though Berg&Berg have regular sales - currently jeans are 50% off), the shoes will be 250-400 and shirts go from 100 to 150. You should consider this as an investment in a core wardrobe: these are pieces that can be dressed up and down as you need, and will last you a long time as long as you clean and maintain them properly. Paying 300 for a pair of chinos that you can wear 2-3 days a week for several years is a decent deal, even if the up-front investment can sting.
 

geg_gee

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Thanks for the advice. Is there any particular reason that chinos are preferred to wool or linen trousers? Easy of care and flexibility?
 

TheIronDandy

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Thanks for the advice. Is there any particular reason that chinos are preferred to wool or linen trousers? Easy of care and flexibility?

Chinos are generally machine washable and quality ones are hard wearing. Wool trousers usually need to be dry cleaned, and flanel (in my book the by far best farbric for casual wool trousers) isn't as durable as a good cotton twill. Linen is only viable a few months a year in Scandinavia, and thus not the first thing to get. If you have a warmer climate, I can strongly endorse heavier Irish linen for trousers - it develops a beautiful patina over time.

Flexibility also plays in; wool trousers will usually look more formal, which limits their use a bit. Once you have a couple of quality chinos, I definitely think grey flanel should be the next thing to get, though.
 

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