Just Starting Out: First Five Pairs of Shoes?

What's everyone's favorite shade of brown to mix with medium gray pants?

The lighter colors (walnut/etc) look too flashy to me. Not sure about burgundy - I feel that works better with navy pants.

Maybe just a very dark brown? Something else? I currently own a pair of black cap toes and a pair of burgundy quarter brogues (the punch cap toe style).

Also, for those just getting into shoes, does anyone else here feel intimidated to wear the more heavily brogued shoes? For a guy like me who's never been a great dresser or pretty plain, I feel like wingtips of any kind would really stand out.

I can name maybe only one person under 40 at my work place (in a very urban city) that would have wingtips or medallions on their shoes.

My take:

1x Black Calf Oxfords (plain or cap).
4x Oxfords. Whatever sensible colour you want; can be suede, calf whatever; and can be wing, cap, or plain. No long wings or heavy broguing - they are, for most part, ugly.

Option - can switch 1 oxford for 1 monk or loafer (no horse bits or tassels)

Done.

Originally Posted by zerostyle

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What's everyone's favorite shade of brown to mix with medium gray pants? The lighter colors (walnut/etc) look too flashy to me. Not sure about burgundy - I feel that works better with navy pants. Maybe just a very dark brown? Something else? I currently own a pair of black cap toes and a pair of burgundy quarter brogues (the punch cap toe style). Also, for those just getting into shoes, does anyone else here feel intimidated to wear the more heavily brogued shoes? For a guy like me who's never been a great dresser or pretty plain, I feel like wingtips of any kind would really stand out. I can name maybe only one person under 40 at my work place (in a very urban city) that would have wingtips or medallions on their shoes.
Brouged shoes don't stand out as anything other than as nice shoes. You don't seem 'em much on a younger crowd simply because the younger crowd is fairly incapable of dressing competently these days. Wingtips were once the great American default shoe. Now the defaults are butt ugly flat toe loafers. If you stand out, it will be in a good way. And yes, dark brown is a nice choice with light gray. Though lighter browns like a walnut aren't as outrageous as you might think. I pair walnut longwings with medium gray all the time, looks quite nice. Throw on a navy blazer and you have a a wonderful, timeless look.

Originally Posted by blahman

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No long wings or heavy broguing - they are, for most part, ugly. Done.
You, sir, will burn in the deepest fires of hell.

1. Black formal
2. Dark Brown formal
3. Black casual
4. Dark Brown casual
5. Whatever suits your lifestyle

Originally Posted by cptjeff

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You, sir, will burn in the deepest fires of hell.
I was born there. I knew it was bound to upset some of you I still don't like brogues and longwings.

So aggregating everyone's comments it seems I need (at minimum):
- A relatively plain black oxford shoe
- A brown oxford dress shoe of some sort
- Double monks (because I want them)

Is that a fair assessment? If so, a follow-up question- while I understand the purpose of the plain black shoe, are there any requirements for the brown shoe(s)? Is it necessary for me to have one plain brown shoe or can I just go with whatever I like ie wingtip or split-toe blucher or whatever?

I ask because I generally like shoes with a little more character than a plain oxford. Would another wingtip be a bad idea or restricting in any way since I already have one? As you can tell, I am a little green when it comes to shoes.

And, for the record, I'm very much enjoying looking at all the CJ's, etc being posted but unless I find really good deals on used shoes (which I'm open to), my price range is probably closer to AD/Alden (at least for now). Thanks to everyone for the input!

No, silly. They were just fooling with you. The correct answer would be Alden longwing in black x 5.

Originally Posted by NORE

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The correct answer would be Alden longwing in black x 5.

That would be Plaza-lasted single sole longwing in shell cordovan color #8.

For the OP: http://www.styleforum.net/showthread.php?t=98968

But seriously, my advice would be:

1) Go black plain (or lightly brogued) captoe oxford if you like the look and/or need highly conservative shoes (for interview or more conservative environments). If you aren't going to wear them, however, skip them and pick up a pair of AE Park Avenues when and if you need them (big interview, etc.)

2) Purchase two-three pairs that you like, that fit well, that you will wear often and that fit your environment, and start there, adding to your collection over time. That is, don't purchase 5 at once because your tastes will change and evolved (alternatively, pick up 5 pairs and never ever ever read this forum again).

Also, for more background context:

1) Oxford/balmorals are more formal and conservative than derbies/bluchers
2) The more brogueing, the less formal. So plain captoe is more formal than a wingtip, for instance.
3) Black is more conservative than brown

All of this means that in a highly conservative environment (London square mile, interview, major presentation), black plain cap toe is the safest bet. If that's not the environment you work in, pick what you like and fits your sense of style.

Can someone do a pictorial version of their five suggestions, for those of us who are visual-minded (i.e. don't like reading)?

Originally Posted by gfreeman

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Can someone do a pictorial version of their five suggestions, for those of us who are visual-minded (i.e. don't like reading)?
From a thread just a few months ago.

Originally Posted by Pliny

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'You have to edit to five pair (RTW) - and only five pair- what stays?' Andrew's answer: John Lobb Jermyn II in dark brown Edward Green Dover in heather gorse Edward Green Malvern in dark oak Edward Green Chelsea in black Edward Green Banbury in mink suede my five: Vass London 3-eyelet in dark cognac Vass Old English in black cordovan Edward Green Dover in dark oak willow Vass London 5-eyelet in tobacco suede Crockett & Jones Onslow in burgundy cordovan

Originally Posted by HRoi

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this thread is a great idea, but only good with pics, as someone already said. i couldn't sleep anymore this morning, so i've snapped a pic of my contribution. a.) this is damn hard! if i ever had to do this in real life i think i would snap and start wandering the streets muttering "arca....chapel....oundle...." John Lobb Vale in chestnut museum on 7000 John Lobb Becketts in black on 7000 Edward Green Chelsea in chestnut on 202 John Lobb Luffield in dark brown on 8695 Edward Green Banbury in mink suede on 606

b.) so i cheated. here is my next five

- i'd put them in the pantry and go without food and toilet paper instead John Lobb Chapel in black on 7000 Vass Austerity brogue in burgundy on U last Edward Green Oundle in dark oak on 888 John Lobb William II in parisian brown museum on 9105 (?) Edward Green Malvern in dark oak/mink suede on 82

Originally Posted by HomerJ

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From a thread just a few months ago.

That's what I'm talking about! If there are other pictorial examples, please post them here.

1. Black Oxfords.

2. Black Derby.

3. Black full brogue.

4. Brown veldtschoen

5. Brown Chelsea boot.

The rationale in this selection is that you can possibly cover every situation except a round of golf. I've not suggested any particular brands, but it (should) go without saying that quality is the best guarantee of value. Church's Oxfords and RMWilliams boots might be a suitable choice in that respect.

Just keep them well polished.

Assuming this is just MC-type shoes and shoes you mainly wear with a suit, this is how I would roll. 1. The boring black captoe - Allen Edmonds Park Avenue 2. The brown punch cap, should see a lot more wear than the boring Park Avenue. - Allen Edmonds Fifth Avenue 3. Wingtip in Walnut, flashier shoe used to pull in womenz - Allen Edmonds Strand 4. Something in Alden #8 - Alden Plain Toe Blucher 5. Monk Straps - Highly up to you I'd say it gets really open ended after the first two pairs of shoes. I was also thinking about a Suede Chukka or a pair of Longwings for that 5th shoe, but since you like Monks then that gave it the edge.

re: whether you should get creative with the first two pairs, IMHO, I think you should get the most versatile shoes you can for your first pairs, and start having fun after that.

Originally Posted by globetrotter

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I'd also say that 3 really good pairs would be better than 5 mediocre pairs, in my opinion

+1 Excellent advice. Quality over quantity. Choose wisely......