Just Starting Out: First Five Pairs of Shoes?

While you can search for the "if you can only own 5 shoes" threads on here that get started all of the time I would say you probably should get something less flashy than a shoe that is walnut in color. I say get a black oxford, or at least a very dark brown oxford so you have your interview/conservative shoe. From there I would move to a wingtip, then a double monk. If budget is an issue you can get good deals on Allen Edmonds and Alden. Then I suggest looking at higher end shoes such as Crockett & Jones, Carmina and so on. Also Cheaney makes a good shoe that is similar in price to Allen Edmonds. Good luck.

You'll need something black. Make it an oxford. Other than that, formality ain't a big issue. Apart from doubling with a tux, a black wingtip is fine wherever a dark captoe is. But black is nice to have with gray and (gasp) black trousers/suits, and you'll need something for formal evening dinners, ect. Sometimes propriety is called for, and you'll want a nice pair of black shoes. So now, we have, say, Black Punchcap Light Brown Wingtip. I would add a dark brown puchcap or half brogue (punchcap with medallion) a la the AE strand next. Since you like monks, get a pair of those. Burgandy, suede or a brown. Basically whatever. Then you should toss a loafer into the mix if you're not wearing exclusively suits. I'm a fan of the classic american style of penny loafers. The Alden Leisure Handsewn is a SF favorite, often in shell.

Black captoe Dark Brown captoe (or anything conservative) Brown wingtip Something in suede (wingtips, plain toe, half-brogue) DC Lewis double monks (Spoo has pictures up, the colour is amazing )

It depends what you do and how casual or formal you like to be? How often do you wear a suit?Also, do you prefer sleek shoes or chunkier shoes?

NOT in order 1. black captoes [default] 2. brown suede penny loafers [jeans/casual] 3. brown split toe bluchers [less dressy] 4. burgundy/brown-black-burnished adelaide brogues [dressy] 5. wildcard: whole cuts, or chelseas, or double monks... suede or calf , personal preference im over the whole chukka thing

I would skip the black captoe.

As far specifically where to look for quality, sleeker shoes, I would take a look at crockett jones mail order (from UK - mail order has more selection than pediwear and the CJ website.) Pediwear.co.uk and bodileys of northampton both have terrible stock shortages right now. Find out how your foot fits the 341 last. You can mail order a pair of Crockett Jones on the 341 from Barneys and keep them or return them (there is about a $100-$150 cost to buy them at barneys over and beyond what you'd pay ordering from overseas - but time, ethical etc considerations )

Also, get a pair of alden shell cordovan shoes. Not a ton of variety, and also not the sleekest, but it's a beautiful, long lasting, unique thing to have.

I'd look at these based on my preferences (in no order)

1. CJ westfield dk brown

2. CJ finsbury chesnut

3. Alden Men's cap toe color #8

4. AS Exclusive Range Moore

http://www.afinepairofshoes.co.uk/co...moore-chestnut

5. Alden NST

http://www.theshoemart.com/alden-men...deen_last.html

6. CJ Arden Tan

7. Peal Split toe Brown (buy on sale for ~$370)

http://www.brooksbrothers.com/IWCatP...tionsize=#null

8. Crockett jones Malvern or a 3 eyelet plaintoe blucher (if you don't want to go monk)

I'm not a shoe aficionado, so don't put much stock into this list, but here's my dream team, all from Crockett & Jones.

Black Hallams: http://www.crockettandjones.co.uk/oxfords-hallamda.html
Chesnut Westbournes: http://www.crockettandjones.co.uk/oxfords-westbour.html
Dark Brown Westfields: http://www.crockettandjones.co.uk/oxfords-westfiel.html
Mink Suede Mertons: http://www.crockettandjones.co.uk/loafers-mertonsu.html

Yummm.

1. Your walnut full brogue
2. Black captoe - AE Park Avenue in black (interviews, funerals, weddings)
3. Brown perforated captoe - AE Fifth Avenue in dark brown (suits)
4. Alden LHS in Burgundy (casual it down)
5. Agreed, I would pick up the DC Lewis monk (fun)

..

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

Here were my first 5 since joining SF (damn you guys for the bad influence on my wallet):

1. Borrelli - Black captoe oxford
2. Santoni - Brown plain toe blutcher
3. Edward Green - Burgundy wingtip oxford (Inverness)
4. Vass - Antique cognac cordovan chukka
5. Crockett & Jones - Cigar cordovan wingtip blutcher (Darlton)

(Actually, 3.5 was JL St. Crepin 2010 but that was a splurge.)

my shoes since joining SF have been: 1) C&J Audleys in dark brown 2) Zee's Black black captoe, basically like the EG berkeley 3) Alden NST #8 Aberdeen (a gift) I'm looking at getting a shoe with rubber soles(not sure what style yet), wingtips, loafers, and double monks in the future. If I were to do it all over again, I'd probably do the same thing, except I'd get rubber soles instead of leather on the zee's. I definitely agree that having 3 nicer shoes would be better than 5 mediocre shoes, and plan to direct my buying in that direction

Brown Full Brogues, Black Full Brogues, Black Monks, Brown Monks, Black Oxford. The reason? I love wingtips and Monks, and Oxfords, while comparatively plain, are basically required.