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Casual shoe investment (+tips)

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    Casual shoe investment (+tips)

    Hello everyone, this is my first post on the forums but I've been lurking for a little while (and, of course, enjoying the content put out on the main site). I'm currently a senior in high school and will be going off to college this August - and I've been wanting to start dressing the part. I don't wear sweatpants and skateboarding shoes, but I'm guilty of wearing ill-fitted $20 jeans, sneakers, sweatshirts, cheap button ups... the lot.

    I don't know where I will attend college (at least for a few weeks), so I thought I'd invest in a few climate-independent basics. For now, that means shoes.

    As suggested per this site, my first actual shoe investment was some chukka boots from Beckett Simonon ( I bought these in January and they've been great to me. I get compliments on them whenever I wear them (granted, it's not much an achievement in high school). Some pictures (I realize they could use a shine):

    I wear these whenever I """dress up""" (meaning, a solid button-up + sweater + fitted dark washed jeans). However, for my casual shoe, I wear these:

    They've served me well of course, but I'd like something better. The criteria are: good looking, comfortable, durable (I can't afford to rotate 4-5 shoes), and affordable for an early college student. I'm willing to make an investment if the shoes will last 10 years, but keep in mind I will be in college, not in the workplace.

    After some research, here's what I came up with... would anyone care to give thoughts and/or suggestions?

    Thank you very much!

    Vare, you can probably get by with a three shoe rotation. As a soon-to-be college student, you shouldn't worry too much about your appearance. Minimal effort will make you stand out in a positive way, and you're already on the road to success with jeans that fit and chukkas.

    The first two shoes that you posted are classic styles. The Clarks driving loafers are quite unattractive. The bass loafer is a classic penny loafer, and should serve you well.


      As a high school senior myself, I can definitely tell you that chukkas are going to be a great piece. You have leather, but if you're not comfortable wearing leather chukkas casually, I personally own a suede pair of clark's desert boots which I get great casual use out of, and a lot of compliments on. I personally have a 9 shoe rotation, but some of the pieces I'd definitely recommend are:

      White leather Jack Purcells. They just look great; no other way to say it.
      Puma trainers, be they hightops or lowtops, Puma just makes a great, edgy looking sneaker. I may get knocked for suggesting this, as they're really anything but "classic," but as a high school or college student, I can tell you that I get more compliments on my Puma's (I have a pair of white and black lows, and a really edgy pair of burgundy hitops) than on any other shoe.
      Bear in mind that you're going to want a pair of just old, functional sneakers if you have an active lifestyle.
      Shoes I don't own but really want to get for college and would probably recommend include penny loafers (I'd say you could probably best be served by finding a pair of AEs off ebay; I know that personally I'm gunning for a pair of westchesters. You could also look into boat shoes if you're going somewhere warmer; I'm definitely going for those two as I'm going to be heading to Cali for school.

      I personally would stay aware from the saddle oxfords or anything too "dressy" like that; I know that by the standards of this forum they're quite casual, but by American college standards they might be a bit uptight. Similar arguments apply to suede oxfords and such.


        You're off to a great start (and good luck on the college decisions!). I was terribly dressed in high school, I wish I had worn shoes like you already have. I'd grab a pair of cheap Bass loafers and call it a day. They'll look great with almost anything and are pretty affordable. Reminds me I need to get myself a pair of Gazelles/Tigers/Sambas!


          I'm partial to moc-shoes myself (in the vein of LL Bean Blucher Mocs or Eastland Falmouths). It's a classic shoe style.


            Thanks for the replies and tips, everyone.

            After looking at the penny loafer a few more times, I am really starting to like it. On a different website I found it for $80. Now, I should know by now that getting something cheap and having it wear out in a few years is much more costly than an expensive item that lasts 10. Is this loafer high enough quality? If not, what should I try to save up for (and why ebay)? Also, are sub-$100 shoes things that merit resoling?

            I like the idea of a three shoe rotation. If I decide to buy a loafer, I would have a leather chukka, a suede/leather loafer (shoe tree for this?), and a third shoe, probably a samba or gazelle or puma, to be functional+decently athletic. Is there anything I'm missing that any decently-dressed college student should have (assuming jeans, chinos, and shorts)? Of course I might buy another pair eventually to spice things up, but I want to make sure I have the basics covered first.

            Thank again for the enthusiastic help!

            (I hear from a few more college this Thursday... so far accepted into UCLA, but the $55k price tag these days is very hard to swallow)
            Last edited by Vare; March 24, 2013, 11:41 PM.




                @Vare- I agree with Los - get a pair or bass into the rotation. If I could do it over again, I wish I could of had this type of forum to help me in the style game. I too was terribly dressed in high school and college. Mickey is correct about this and some of the other forums, the casual look here isn't sweatpants, hoodies and new balance- but this is a good place to learn and understand a style, quality and value.

                I would say a penny loafer with a stacked heel might be a little much as a freshman- even at a large place like UCLA. A driver with a boat or penny loafer look would seem better. The leather chukka you already have - good choice - and then the bass for an upgraded look. If you do a suede driver you could look at the brown claiborne blucher at JCP for $60. That has potential to be a very versatile shoe as well. That last clark driver shoe you list, I would not recommend it- too square of a toe for my taste. Since it sounds like you are starting to look for a style to get into - I wouldn't jump into any high dollar shoes just yet. Two years into college you may find that you want something else- doesn't make a lot of sense to drop serious $$$ right now. Shoes costing less than $100 will last a while if you have a small rotation (2-4 pairs). If you go with JCP stuff- look into gift or those sites regularly have 20% gift cards - really helps on the savings.
                Recommended Rotation (if you are buying 2-3 more and probably in this order):
                -current leather chukkas
                -You probably have a pair of running/cross trainers
                -Bass or
                -White canvas
                -Drivers (I'd to with the Tan or olive or darker brown)
                Last edited by ajk170; March 25, 2013, 12:49 AM.


                  By functional/decently athletic, I meant a shoe totally separate from your 3 shoe rotation; something like a New Balance or asic. You don't have to spend a lot of money and it doesn't have to look good, but if you want to, say, play Ultimate in the mud, you're not going to want to be wearing anything you have in your rotation. Not so much style advice as lifestyle advice, I suppose. This is assuming you'll be running/hitting the gym/playing sports.

                  As far as the loafers go, I personally prefer an all leather look, but I think that's down to personal preference.

                  I see you're braced for Ivy slaughter day. Let me know if you get good news Friday (I'll leave it to you to figure out which school comes regular decision Friday =P ) And good luck, of course.


                    I can tell you that I get more compliments on my Puma's (I have a pair of white and black lows, and a really edgy pair of burgundy hitops) than on any other shoes...


                      Perhaps a fasion sneaker:

                      or desert boot:

                      Sperrys aka boat shoes:


                        Appreciate the suggestions once more, everyone!

                        Mikey, I prefer leather as well, though I'm always a bit worried if they'll crack or get wet. I guess that's one of the positives of purchasing sub-$100 shoes. Indeed, 4 decisions come that day for me. Does Harvard release on the 29th?

                        ajk170, thanks for the warm reception and understanding response. Would I be correct in saying that the Bucks (Bass Brockton/clairebornes) are more formal than the chukkas? If so, in what different situation would I wear them (as in, what outfits? OCBD?). At this point in my life the chukkas are relatively formal, so I'm not sure what I'd wear the bucks with; unless one was suede and one was leather, then I could understand the difference (a bit). I'm very much a newbie at this so any and all advice, anecdotes, examples, etc. is very useful.

                        The Jack Purcells and Pumas both are great - I might lean towards the Pumas as I like the feel/look of suede a bit more than canvas.

                        I am also leaning more towards the drivers than the sperrys, simply because it's been drilled into my mind that sperrys = typical college frats. I assume this will be a shoe more useful in the summer as it is lighter (or, could I wear all in the summer). The Polo drivers you linked, ajk170, I like in tan, but the reviews are rather negative so I will shop around for something similar.

                        I summary, I believe I will be buying:
                        -Something similar to this in tan:
                        -This in Taupe:
                        -A puma, or similarly good looking sneaker, like this:

                        Again, I aim to cover the basics of what type of shoes I will need in college, to start building a modest but stylish wardrobe. The essentials, if you will.


                          Originally posted by Vare View Post
                          Appreciate the suggestions once more, everyone!

                          Mikey, I prefer leather as well, though I'm always a bit worried if they'll crack or get wet. I guess that's one of the positives of purchasing sub-$100 shoes. Indeed, 4 decisions come that day for me. Does Harvard release on the 29th?
                          I suppose that the whole cracking or getting wet thing is going to be very climate dependent, although personally I really don't think suede compares to leather at all, especially if you're going to be wearing a sleeker shoe. Suede just has an image of bulk to me; it's not as streamlined. Although I do agree that suede is superior to canvas, the pumas I own are a lot like the whirlwinds, but in leather. More like this: without the suede tips at the toe.

                          Actually, Harvard is also the 28th. Not a bad guess though.


                            @vare- others can correct me and if they do- take my opinion as just that - but a suede bass is similar in caliber to a suede chukka with the caveat being a creped sole chukka (or a non-stacked sole chukka) could be a little more casual than the a suede buck or a rubber/leather stacked heel on a leather chuckka.

                            Where would I wear bucks/bass? Everywhere. When I wore chinos or khakis to class I wore a great pair of $60 bluchers (for me it was a pair or Nautica's that I really loved and got rid of several years after) or boats (depended on the season). I wasn't in a fraternity but I noticed those guys dressed pretty good. Plus, when I dressed in more than a hoodie and jeans I worked harder. I didn't own chukkas back in college- didn't really know about them but if I had, I would wear them in jeans and chinos. Suede bucks can be worn in jeans, but I suggest darker jeans- Like Joe and many others say, stay away from stonewashed.

                            If your chukkas are pretty formal for you, definitely go with a very casual suede driver and leave the chukkas in reserve for the Thanksgiving Dinners or meeting a girl for a nice date.

                            What to wear as a shirt? Well, I belong to the SOT that men only wear collared shirts in public- college isn't too different so any type of collared shirt, crew/v-neck/henley without a collar is ok but a T-shirt by themself is a no-go for me except at the gym, the dorms, or sometimes at the beach. The caveat there is University T-shirts and I had a few that I wore but there weren't many.

                            @mickey- good call on the pumas! That's a good shoe that doesn't look like you're trying too hard...