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Serious fashion advice

dieworkwear

Mahatma Jawndi
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I have a pair of tailored Hugo Boss dark grey trousers bought from Saks a few years ago. They have been worn very little. I wore them for a T.V. commercial a couple of months ago.

What is the opinion on Hugo Boss look/quality? From my limited experience it is good.

I know that there is a guy in NYC that does hand tailoring and builds from kits. He says that he can usually tell measurements by looking at someone on camera. His prices were pretty reasonable too. I don't recall the name but I could find it.

I am wondering if he could work up something by Hugo Boss (blazer and shirt), or another Italian brand.

Any opinions on this approach?
There's not really a way to give feedback without seeing the clothes on you. It may be that Hugo Boss fits you well; it may be that it fits you poorly. There's no "one brand" that just solves everyone's problems. It's about finding clothes that fit you.

Personally, I wouldn't do one of those remote Zoom fittings. Custom tailoring relies on many small details and I wouldn't trust that would come through a Zoom call.
 

dpatton75

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I know some women that will give me feedback.

I was thinking of pairing those Hugo Boss trousers with a dress shirt from Paul Smith, Bonobs, ledbury, Twillory, or Hall Maden. Unfortunately I don't have time to have them tailored but supposedly some of these listed to a good job if you send your measurements.

I already have Allen Edmound dress shoes (need polishing up) and a dress belt.
 

Phileas Fogg

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I know some women that will give me feedback.

I was thinking of pairing those Hugo Boss trousers with a dress shirt from Paul Smith, Bonobs, ledbury, Twillory, or Hall Maden. Unfortunately I don't have time to have them tailored but supposedly some of these listed to a good job if you send your measurements.

I already have Allen Edmound dress shoes (need polishing up) and a dress belt.
you’re throwing a lot of brand names around. Don’t worry about the brand. Worry about how the clothes look on you? Do they fit? Ill fitting clothes from a high end boutique will lose out every time to properly fitted clothing from JC Penney or Kohl’s.

I agree with the above, talk of pairing this with that is moot. Post some pics otherwise any advice or feedback we give is meaningless.
 

Leiker

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How long until this date? You bring up custom tailoring, which can take a while.

Also, you indicated that you want to dress for a formal dinner. Why not wear one of your suits?
 

ter1413

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Don't overthink this.
 

dpatton75

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Due to Covid I was doing most of my work from home. I have found that most of my suits no longer fit. The dress shirts do but the trousers are too tight around the waist. My Allen Edmounds belt no longer fits either.

I have wore these clothes for a few years through serious hard use anyways. I think I will take the opportunity to completely revamp my wardrobe for work also.

Since I last bought dress clothes several years ago (Brooks Brothers and J. Press mostly), these new companies I mentioned above have become a thing and I want to try them.

I did decide to just wear one of my suits until I got them out and started to try them on. :-(

I feel like I am flushing a lot of money but realistically, I have gotten more than my money's worth of use out of them.

I have found J. Press quality to be top-notch.
 

rjc149

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I have a pair of tailored Hugo Boss dark grey trousers bought from Saks a few years ago. They have been worn very little. I wore them for a T.V. commercial a couple of months ago.

What is the opinion on Hugo Boss look/quality? From my limited experience it is good.

I know that there is a guy in NYC that does hand tailoring and builds from kits. He says that he can usually tell measurements by looking at someone on camera. His prices were pretty reasonable too. I don't recall the name but I could find it.

I am wondering if he could work up something by Hugo Boss (blazer and shirt), or another Italian brand.

Any opinions on this approach?
My Hugo Boss suits did not hold up well, particularly the trousers. The pocket seams were threadbare after a year. They also had slim lapels, which I have since eschewed in favor of the more classic and timeless 3-inch width. I've avoided Hugo Boss since.

I'm late to the party here, but as general advice, spending money trying to impress a woman (who you haven't yet banged I'm assuming) is a baaad way to go dude. It's try-hard and approval-seeking. It says "I hope she likes me." You're going on a date with a "serious woman" who is a "10/10" -- see? You've already got her on a pedestal because you've judged her value to be higher than yours. This is fundamentally unattractive to women.

Your attitude going into a date should be "I'm trying to figure out if this woman will be good for me." Convey that YOU are the one whose approval must be attained. Don't care about it that much. She likes you? Cool. She doesn't like you? Cool. Next.

Dressing up for dates beyond what's called for also places undue formality and expectation on the date. Women don't like men placing expectations on them. They don't like feeling like you've spent money on this date -- for a specific desired outcome. Unless it's after work and you work a white-collar job, showing up to a date in a suit and tie will be totally overkill and try-hard.

A nice pair of slim slacks, nice brown brogues or loafers maybe, and a fitted shirt with a collar (polo or button-down) would be perfectly fine for any evening outing with a woman at your age. It shows that you dress nicely and take care of your appearance, but that you're a socially intelligent, high-value man with other dating options, and don't need to impress anyone.
 

dpatton75

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This is no longer about dates. I am buying new work clothes.
 
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Phileas Fogg

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This is no longer about dates. I am buying new work clothes.
when you go back to the office start hitting on the single ladies you work with. Trust me, they’ll love it. That way your work clothes and daring clothes will be one and the same.
 

maxalex

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No one here would discourage you from building a new wardrobe if that’s what you want, but why not also just get your current suit trouser waists altered? Assuming your weight gain has not been extreme, it’s easy to let out the waist a bit.

Just don’t wear a navy suit with a white shirt and no tie, you’ll look like every boring banker at Friday night happy hour. A suit with no tie should compensate with a patterned or colorful shirt (“fantasia” we charmingly call it here in Italy) and a pocket square.
 

breakaway01

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Convey that YOU are the one whose approval must be attained. Don't care about it that much.
...
A nice pair of slim slacks, nice brown brogues or loafers maybe, and a fitted shirt with a collar (polo or button-down) would be perfectly fine for any evening outing with a woman at your age. It shows that you dress nicely and take care of your appearance, but that you're a socially intelligent, high-value man with other dating options, and don't need to impress anyone.
Uh...okay. I guess it's been a while for me, but these are very interesting attitudes. I don't really think about it as a game where I need to convey the message that I'm the one who should be impressed. You seem to think that the interaction must necessarily be unequal (one party needs to impress the other). I prefer to think about it as an interaction between equals, and in that context why wouldn't I want to look good? I would hope most women would think the same way. Though you seem to be very confident about what women want and think.
 
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dpatton75

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If trousers are a bit (.5 to 1 inches) to large in the waist, can a competent tailor take them in a bit and retailor them to look good?
 

rjc149

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Uh...okay. I guess it's been a while for me, but these are very interesting attitudes. I don't really think about it as a game where I need to convey the message that I'm the one who should be impressed. You seem to think as that the interaction must necessarily be unequal (one party needs to impress the other). I prefer to think about it as an interaction between equals, and in that context why wouldn't I want to look good? I would hope most women would think the same way. Though you seem to be very confident about what women want and think.
Women are generally more attracted to higher-status men. Not every woman, and not always, but generally speaking. You see this play out everywhere, again and again, so I’m not going into the theory on that. Let’s just agree that it’s a self-evident truth about dating and attraction.

Your attitude seems to be “she is above me, therefore I must impress her by going up to her level.” You were about to drop some serious coin on an outfit for this date — that means you are probably far more interested in her than she is in you, and your expectations on this date are too high.

Generally speaking, you want to have an authentically confident, non-needy, and dominant frame on dates. Again I’m not going to delve into the theory here or go into an “alpha vs beta” dichotomy, but generally speaking, women are attracted to men who display an “alpha” mindset. Meaning that you are already awesome, so you don’t need to buy an expensive suit in the hopes that your date will be impressed and have sex with you.

The mindset isn’t a game. It’s not treating women like they are beneath you. It’s a mindset that you are worthy on your own merits. That because you are an attractive man with abundant options, you have zero expectations on her. You are totally outcome-indifferent. She can stay or go, no problem. You don’t care that much. The next bus comes in 5 minutes. No woman’s beauty places her value above yours.

No, don’t show up in jeans and Underarmor gear. Yes, dress well. But women are more at ease with men — and more attracted— who aren’t fawning over them and trying to impress them with flashy clothing and expensive restaurants. She hasn’t earned that from you yet.
 

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