Which Style Shoe for 1st Upgrade?

OK, I was set on getting a pair of cap toe shoes for my first upgrade, but after reading an article on Real Men Real Style, it also mentioned the pointed/narrow toe style. I’m 5’10” & 170lbs… basically medium build. Which style shoe should I select?

Also, Im around a lot of european people from various groups of friends and from traveling. I dont have a photogenic memory, but I do recall shoe styles are a bit different. One example is sharply pointed toes (both men and women). Im confused now on which shoe would best suit me. I like the cap toe style on a personal level, but narrow style might better suit my body and possibly the circles of friends.

Any suggestions on this? Thanks.

6 Replies to “Which Style Shoe for 1st Upgrade?”

  1. I would start with a black Oxford cap toe. Of all the shoe styles out there it is the most versatile. After that. Guy the same in brown or ox-blood. Your third pair should be a brogue or a loafer. Either one will do and your fourth will be the otherof the two. These are your staples and will actually be all you’ll need in shoes aside from maybe some converse sneakers. I would stay away from toes that are too pointed since those suffer from fashion whims.if pointed toes is going to be your signature look though, then I’d say go for it. The first pair should have a rounded toe though for job interviews and other occasions where you will be required to dress conservatively.

  2. Awesome, thank you. I ended up with a pair of black cap toe for my first pair. Since I travel I am also considering a pair of monk straps. And then my first brown pair after that. I really appreciate all the help!

  3. I have had the same pair of black cap toe shoes for over 10 years and they are still very much in style. I have worn them to numerous occasions. Including putting many dancing miles on them and have been stepped on many times by dance partners and bridesmaids. I have one battle scar from a sharp stilettos that hasn’t quite buffed out. Get the best quality pair you can afford and they will last many years and still look in excellent condition with the occasional buff and polish.

    I think oxblood is one of the most underrated leather colors you can wear. It looks really sharp with many colors, the hardest part is finding a belt to match.

    I also have a pair of black semi-pointy loafers but those are for casual wear to informal events only. Its hard not to find casual pointy loafers from most designers nowadays. In Europe and other countries they are much longer and pointer than what you will find in the US. It has been the fashion trend for well over 5 years and it seems like it is here to stay for a while, sort of like flat front pants. Most italian made shoes have that very narrow pointy look its very common in Europe. It looks really good with very slim fit trousers that are not so common.

  4. I remember reading somewhere that you can wear oxbood shoes with a brown belt as long as they are of a similar hue. I have a pair of oxblood cap toes and that’s how I match them with a belt. I probably should hold off one the shoes until I find a better matching belt but I love how oxblood looks with my navy pinstripe suit. I never did like brown with navy and I don’t want to wear black with all my suits. I usually go with charcoal grey suits and they go best with black shoes.

    Monk straps can be a good second shoe. I wouldn’t spend less than $500.00 on a pair of monk straps. Monk straps are not as common in the US so they tend to make a statement. If you are going to make a statement then you might as well spend on higher quality.

    Hmm .. I suddenly got inspired to go out and look for a pair of oxblood monk straps. Something new for my wish list 🙂

  5. To add again to Nicholas, and to add to my comment on your other shoe question, I’d say a great cap toe oxford to start with is the Allen Edmonds Park Avenues. Like I said, you can probably find a decent used pair on eBay and have it refurbished sooner or later depending on the wear of the shoes.

  6. Great Info here… I agree with Nicholas and Mr Modern…
    I am hooked on Edmond Allen Shoes, and the S. Ferragamo, I have Both Brown, and Black Toe Caps, Black Wing Tips, Edmond Allen Fairfax, which I love.. it is a single leather construction, and they look classy. I do have a pair of S. Ferragamo Monk Straps…

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