See, Sunspace, “I need help getting dressed” IS a girl attractor!
Whereas most men prefer to help a girl undress!
Thank you! I like the idea of dark, intense, jewel-like colours. Green, red, dark gold, burgundy, dark blue.
“Dark bold”. I like that.
:: contemplates the artistic possibilities ::
Why, thank you. Here are some pictures of me:[ul][li]Four years ago, at a work dinner.Many of you have probably seen this picture before, but it is not really representative or me anymore.[]Two years ago, at an outdoor exhibit of African sculpture (totally amazing exhibit, by the way).One of the few pictures I have of me standing up. []Two weeks ago (sorry for the crappy phonecam picture)[/ul][/li][quote=Oy!]
Your taste in clothing sounds classic and hard to go wrong. It used to be called Ivy League back in my youth, then Preppie, now just “business casual.”
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I always associate Preppie with short-sleeved golfshirts in brighter colours. Hmm.
That’s the second time I’ve heard that about pleated pants. Interesting. But, if you actually do have a few extra pounds around the middle, how do non-pleated pants work, or even fit well?
Maastricht, Freudian_Slip, I’ve ordered Dressing the Man, Carole Jackson’s Color for Men, The Mature Man’s Guide to Style, and Men’s Style from our friendly public library.
Time to explore.
When I was going to the screenwriters’ meetings last year, there was a women there who had a grey-blue shirt the same colour as her grey-blue eyes. The effect was most… intriguing. If only she hadn’t smoked… :: sigh ::
:: blush ::
Oh, and everyone, thanks for the tie and shopping advice. 
Sunny, me boy, I would strongly urge you to get some shirts/sweaters in royal or sapphire blue. Here’s a dress shirt , here’s a clear blue polo shirt , here are navy blue non-pleated trousers , here’s a multi-stripe (but mostly blue) oxford shirt (Only the color multi-stripe - the others are too loud or too pastel) , and here’s a navy blue heather turtleneck for starters. The heathers are particularly nice.
Based on your pics, the jewel tones will all work quite well with you, as will white or grey (particularly if you have a tan). And don’t neglect orchid/violet/lavender in casual shirts - those shades of slightly purple-ish blue will work very well on you. When fall rolls around again, they’ll have a fantastic selection of crew and vee-neck sweaters, many in the heathery shades that I think work better on most folks than the clear colors. Burgundy can’t help but be great on you, and the ruby reds and emerald greens will also fly quite well. Colors that wouldn’t work particularly well for you are the very light pastels, peach, aqua, beige, and many shades of brown/tan. None of these will look *bad * on you, but they won’t enhance your looks at all.
Hie thee to a good hair stylist, and pay attention to what s/he is doing while you’re there. From the pics it looks like your hair is like mine - fine and lacking body. A good hair stylist can work with that, and you can then usually risk going to a less expensive place for maintenance cuts. But do NOT go for a spike or crew cut; those looks would not suit your face or body type. You need a bit longer, softer look around your face, as do most people. If you wear glasses at all, stay away from the dark-rimmed horizontally oriented frames that have been fashionable over the past ten years for some incomprehensible reason (they look good on only a very few people). You would want rimless or very thin wire rims in an unobtrusive color. In metals, you should always wear silver, platinum, gun metal, pewter, etc, not gold or copper. Again, it’s not that the latter will look bad; it’s just that the grey metals will look much better.
My final advice is this: get your hair styled, and buy one pair of trousers and a single dress shirt. If you can bring yourself to wear it, a tie would be good too. (I happen to worship Paisley myself, but not everyone does). One outfit; that’s all you need. Then go out and meet some women. For this purpose, try to pick one who looks like she didn’t sleep in her clothing the night before - hopefully some woman who gives you a vague impression of elegance without suggesting that she would accept (let alone insist upon) $300 shoes or trendy designer labels. Once she’s dressed for the evening, she really shouldn’t be considering her appearance at all except when she hits the ladies room (“oh shit, I just ran a stocking” or “Damn! I broke a nail” don’t count unless she then obsesses about it for the rest of the evening).
Spill your soul - the truth, the whole truth, and nothing but the truth. Explain that you want help in building a real wardrobe now that you’re out of the Early Orange Crate stage of your life, and that her appearance suggested to you that she would be a good person to ask to go with you to shop. *Don’t * push it as a date; she would simply be doing you a favor. There’s probably not a well-dressed straight woman in the world who wouldn’t be half-way seduced by the prospect. But get her to go shopping with you a time or two before you actually make any moves - then if it goes sour, you’ll still have gotten the benefits. Psych studies have shown that the single best thing you can do to make someone like you better is to ask them for help in some area. Among other things, it’s a compliment of the highest order, since it is a tacit statement that you admire their competence in the area of interest.
So: one hair style, one nice outfit, and then sally forth to find the assistance you need. Don’t worry about fashion - the only reason other than warmth that clothing serves is to make you look better. The same with hairstyles. So often you see people of either sex who are wearing the style du jour, and it simply looks like utter hell on them. If you strive for a more classic style, you never have to worry about it.
This is the time for you to impose on one of your married friends. Pick a couple with good taste in clothes and ask them to go with you. Get them to dress you. They know you far better than any of us.
Apart from when I thought you said leathery instead of heathery and got confused, this sounds interesting. I am imagining stronger colours than those you linked to, though.
I’m letting mine grow out again. Six years ago, I looked like this, but I cut it after I started to go bald. As I mentioned before, I do not want to combover, so now I have to figure out how to balance these needs.
And after I just spent $450 on the glasses you saw in the most recent picture! They were picked out by the assistant at the optometrist’s, and weren,t what I was expecting at all. I have gotten good comments on them. My previous glasses were rounder. Maybe my next ones will be frameless.
I never wear gold.
Hmm. Maybe next payday…
This may cause me to choose slightly-different women at LavaLife
Now I’m thinking, “apartment makeover”…
Okay, maybe LavaLife wouldn’t be the best idea here.
But who do I know who knows about this kind of stuff and dresses “well”? I’m reluctant to ask the women at work, who are the greatest pool of well-dressed women I’m acquainted with. :: ponders :: Quartz, your idea is good.
Thannk you. A restrained classic style is what I’m looking for, but it has to be the right restrained classic style. 
Incidentally, the first of those books about style is in at the library. I can pick it up on Monday. I will crack this problem. It’s small compared to other problems I’ve cracked in the past ten years.
I use one of these;
The Why Knot?
Just don’t put your neck in while its working. That’s the mistake I made.
If you go to Holt Renfrew or Harry Rosen, they spend a lot of time with you picking out the right suit that looks good on you. That has been my experience with them when buying a suit for my husband to get married in. They also tailor it for you so that it fits right and falls nicely. Banana Republic sells nice mens clothing which is a bit cheaper. Also Toms Place near Spadina sells upscale mens suits, but I’m not sure if they tailor and fit them.
Please remember: Pleats are for school uniforms, not for grown men.
Those glasses look very good on you.
Thanks! 
A long, long time ago I was informed that when a man gives clothes to a woman he’s supposed to help put them on - and later, take them off.
Sunspace You’ve gotten a lot of good advice in this thread. If I might add one thing that would be stop wearing tennis shoes/sneakers/athletic style shoes. To me they are too casual for even casual wear. My personal philosophy is that I don’t wear athletic shoes except when I’m working out. Any other type of shoe is always going to give you a more put together appearance and there are plenty of comfortable, casual shoes out there. Loafers or even sandals (but not flip flops) look better than sneakers IMO.
I feel almost as strongly about denim. To me jeans aren’t particularly comfortable and any other type of casual pant will look better.
If you’re thinking about casual slacks I’d like to recommend flat front. In my opinion almost everyone looks better in flat front slacks versus pleats. But that’s just my opinion.
You don’t have to spend a bundle on a suit. The last suit my husband purchased was only $200 at a nice department store and they tailored it for nothing.