yeah, yeah, sho shoe me
June 10, 2013 7:18 PM   Subscribe

Mid-to-late twenties male looking to buy a pair of shoes that's more attractive than a sports sneaker and less formal than a business/dress shoe.

I'm one of those people who has basically always owned two pairs of shoes at a given time-- one pair of New Balance (or the like) sneakers for my personal life, and one pair of nice shoes for work and fancehhh events. I want to get a middle path shoe! One that will make me look good!

I'm basically looking for something that could be equally appropriate at a laidback party, on a casual date, or at a very informal professional event (say, a networking happy hour). Essentially something attractive that makes sense to wear anytime I'm going into public and not exercising or jobbing.

Vague guidance points:

--Not into the preppy look; I'm not trying to come off like Tagg and Trigg chilling on the family yacht. Boat shoes are not in my future.

--I'm told that I have a tendency towards wearing "earth tones"; dark green, brown, etc. Plaid and stripes too. My crowd, I guess, tends to be late-twenties/early-thirties crunchy nonprofit-worker types, not incredibly attuned to style but with a vague urban hipster look by osmosis.

--Visually-aesthetically, I tend to be attracted to things that look rough, textured, warm, wabisabiescent, over things that look glossy, bright, sleek, metallic.

--I'm willing to pay extra for something from a company with attested good labor/environmental practices; controlling for that, I definitely like to get a good value, and I don't have a whole ton of money to fling around.

I'm just kind, and I have trouble conceptualizing what-all types of shoes I could even wear, if that makes sense. I just want to be able to look a little more stylish than either "just got back from a run" or "off to the big interview". So feel free to suggest something super-common or basic; don't assume that it's something I would have thought of.

posted by threeants to Clothing, Beauty, & Fashion (29 answers total) 19 users marked this as a favorite
Chukka boots.
posted by mollymayhem at 7:30 PM on June 10, 2013 [2 favorites]



posted by deanc at 7:34 PM on June 10, 2013 [1 favorite]

Response by poster: Thanks so far! Some of these are really cool. If I can be slightly picky (though I hugely appreciate the links), I'd prefer being pointed to specific shoes that y'all think look great. Then I have the option to fan out to the company as a whole if I like what I see. But seeing a giant e-wall of shoes sparks the same sort of "aaaaaah how am I supposed to synthesize this, which ones look good, eakjrngktdndnj" overwhelmption that makes this question difficult for me to sort out for myself in the first place.
posted by threeants at 7:41 PM on June 10, 2013

TOMS' men's line is pretty excellent these days.
posted by These Birds of a Feather at 7:46 PM on June 10, 2013

'd prefer being pointed to specific shoes that y'all think look great.

Well, that's an awful lot of work on our part.

But think about a pair of "casual" shoes that you wouldn't wear to a business meeting or a funeral but still don't look like you're wearing a pair of hiking boots or sneakers.

Brown shoes like these

Campers like this or this or this.

MeFites frequently suggest Cydwoq which I linked to above. They are not my style, but from what you describe, they're your style.
posted by deanc at 7:47 PM on June 10, 2013 [1 favorite]

I really like Clarks casual stuff, specifically the Roar. Meets your requirements as far as I can see, and the friend who recommended them to me has some fairly serious urban fashion cred, so they work on that score too.
posted by Alterscape at 7:50 PM on June 10, 2013

The Horse. Great shoes, lovely leather.
posted by His thoughts were red thoughts at 7:54 PM on June 10, 2013

You are unquestionably looking for Blundstones. They're so incredibly versatile and they just look better the more you wear them and bang them around. Super comfortable, too, and easy to care for. As a bonus, they're just uncommon enough to give you serious cred among people who know their style.

The style of boot with elastic on the sides is called a Chelsea boot, though Blundstone is more rugged looking than most. But it's good to know if you're looking at other companies (Timberland often makes some interesting options).

Keens are very popular in your demographic. You might try something like the Finlay (Austin is a very similar style), but you've got other options.

How about a more neutral, sleeker semi-athletic shoe like this Merrell?

My brother got my whole family hooked on Tsubos. Black laceups. One of their more sneakery styles (though I would never classify it as such). If they don't strike you right now, wait a few months and see what else they come up with; they usually come up with new styles fairly frequently.

Fryes will last forever.

If any of these look tempting but perhaps a little spendy, Google a little more and you can probably find a deal.
posted by Madamina at 8:04 PM on June 10, 2013 [1 favorite]

I like the Merrel Jungle Moc for casual times. It's just dressy enough, very comfortable. Merrel seem like a decent company too, but I haven't done any real research into them
posted by IanMorr at 8:07 PM on June 10, 2013 [2 favorites]

I like classy moccasins like these. They seem to strike the balance you're looking for.
posted by saul wright at 8:15 PM on June 10, 2013

I really enjoy the whole line of Steve Madden for Men

They have a range of styles from casual to dressy and in between. Some will go into the preppy area, but some are very classy but not boring.

You can also find them locally at places like DSW Shoes. (And probably Famous Footwear too?)
posted by Crystalinne at 8:19 PM on June 10, 2013

My boyfriend's shoes that fill the gap you're looking to fill are these Clarks- he has the tan, which are more weathered and less shiny than the brown. These, which are still on the Clark's website, look pretty similar but a bit more formal. They're nice because they dress up jeans but can work in a slightly nicer outfit with khakis or whatever.
posted by MadamM at 8:20 PM on June 10, 2013 [2 favorites]

I second MadamM. Those will work with slacks and a sport coat, but they will go great with a pair of jeans.
posted by yeolcoatl at 8:34 PM on June 10, 2013

I helped my former boyfriend pick out some Ecco shoes that were similar to this. If I had a current boyfriend I'd probably advise him same :-)
posted by mermily at 8:35 PM on June 10, 2013 [1 favorite]

You say that you're looking for one pair of in-between shoes, but I think that you probably need two; one pair of basic sneakers and one pair of nice semi causal leather shoes. Leather sneakers would sort of split the difference, but I think they get the worst of both options and the best of neither.

For the sneakers, I would go with a pair of navy or grey Vans lace ups (you have to click "more colors"). BUT! Take out the stock laces and replace them with leather laces (which you can get at most shoes stores and/or craft stores). IMO that really takes them into the anywhere/everywhere level, and I bet would vibe with your personal preferences. Buy the 72" boot lace and cut one in half for two shoes. Then you also have a replacement set!

Those oxfords that MadamM linked are a good option for the second pair. What you're looking for here is a non shiny pair of leather shoes. If you're into the traditional oxford style, those are a great bet. Other options are the chukka, as mentioned above. Clarks Desert Boots are a good option. I live in a northern climate, so for most of the winter I wear these boots, which I love.

Best of luck! If you want some help conceptualizing all of the kinds of shoes you could wear, try this Reddit Men's Fashion Advice Thread. It's fairly exhaustive.
posted by daniel striped tiger at 8:48 PM on June 10, 2013 [2 favorites]

posted by brujita at 9:11 PM on June 10, 2013

Timberland has some nice shoes. Atlantic Edge is called a boat shoe, but doesn't look like a boat shoe. 3-eyed oxford is very similar and it is a heavier shoe.

My younger brother wore a pair of these for years, they looked great. I'm not sure which of the above styles the shoes were, as they look very similar to me.

Sanuk Kingston and also Rambler would look nice.

Do you prefer slip on or lace up shoes?
posted by JujuB at 9:43 PM on June 10, 2013

I think what you want is either a boot (e.g. 1, 2, 3) or a dressy sneaker (e.g. 1, 2).
posted by RogerB at 10:02 PM on June 10, 2013

Clarks Desert Boots, leather or suede. They fit your aesthetic well.
posted by schoolgirl report at 3:51 AM on June 11, 2013

--I'm told that I have a tendency towards wearing "earth tones"; dark green, brown, etc. Plaid and stripes too. My crowd, I guess, tends to be late-twenties/early-thirties crunchy nonprofit-worker types, not incredibly attuned to style but with a vague urban hipster look by osmosis.

--Visually-aesthetically, I tend to be attracted to things that look rough, textured, warm, wabisabiescent, over things that look glossy, bright, sleek, metallic.

On these two points alone, you sound a lot like me.

I almost always wear shoes in this zone unless i'm having a lazy day or something. I like these clarks which look good with basically anything that involves pants, a pair of these justin lacer/roper boots in dark brown(the pictures on their site sucked and were a poor example).

If i wanted to buy one pair of shoes for this purpose, and only one, i'd be very torn between the clarks and these red wings specifically because they're both the most comfortable shoes i've ever walked around in.

I also think there's another angle to attack this from though, in a similar vein to the lace up vans above. And that's classic looking leather sneakers. Something like black on black leather chuck taylors, or these (also). Basically anything from this results page or the similar "vintage" pumas. I find that these look perfect after they've been worn in just a bit and strike that balance between "i threw these on this morning because i don't care how i look, and they're from walmart" and "i'm dressing up for something". They look deliberate, but not dressy. Don't like white shoes? the black or darker color ones are just as mildly classy. The white ones work great with my dark wash jeans and plaid/flannel shirts though.
posted by emptythought at 3:54 AM on June 11, 2013

I've been buying merrel jungle moc for 10 years for these reasons as my daily 'all purpose' shoe ; I'm probably on my 12th or 13th pair. It does well, although I think the quality has been slipping.....they wear out quicker than they used to.
posted by lalochezia at 5:33 AM on June 11, 2013

+1 to the Keens; I'm pretty much never going to buy another brand of shoe. I'm wearing the Austins right now, but also own the Voyageur for outdoorsiness, and the Steel-toed Detroit Mid for keeping my toes intact at work.
posted by jeffjon at 5:42 AM on June 11, 2013

Work boots are very trendy right now:

Alden Indy ($500, made in the USA)
Wolverine 1000 mile boots ($355, made in the USA)
Red Wing Iron Rangers ($223 - $300, made in the USA; Red Wing also makes some moc toe/crepe sole boots which are popular though not my taste)
Thorogood American Heritage $124 - $143
Chippewa 6 inch boot $103 - $149

Maybe think about some bucks. I also know people were pretty big on Common Projects sneakers, but they're not really my taste so I'm not up on what's in there. Driving shoes seem pretty common these days, but I'm not into them either, so ...
posted by Comrade_robot at 5:43 AM on June 11, 2013

If you like the Merrell mocs that IanMorr mentioned, check out these LL Bean shoes (,a href="">1, 2, 3). My husband has a these in both tan and black and loves them.
posted by aimedwander at 6:54 AM on June 11, 2013 [1 favorite]

In the boot vein, I recently helped my boyfriend pick out these Timberland Earthkeepers, which fit several of your criteria:

-Not preppy
-Earth toned: dark green, brown, etc., vaguely hipster
-Rough, textured, warm

The boots come in several different colors, I prefer the darker brown over the auburn color, but both are pretty nice. You can wear them laced up under dark jeans (I don't love the cuffed jean, but couldn't find many photos), or wear them loosely/lazily laced and flappy with jeans tucked in.

They look good with narrow legs, muscular legs, and larger legs, whichever you may possess.

If anything, avoid the 'fancy faux leather sneaker dress shoe' that seems to plague the field of men's shoe options. It is not a good look.
posted by rachaelfaith at 7:09 AM on June 11, 2013

Allen Edmonds Black Hills in Walnut ($295, made in Wisconsin since 1922). They can be recrafted.
posted by probablysteve at 7:13 AM on June 11, 2013 [1 favorite]

I'd suggest a brown suede oxford. There are lots of them out there at all kinds of different price ranges. They are pretty trend resistant (as long as you don't get the bright colored or white soles). They will last forever and can be resoled if you get good enough ones. They straddle the business/casual line with ease and a laid back style.
posted by srboisvert at 7:20 AM on June 11, 2013

my husband has been trying to upgrade his footwear in similar ways to what you've described, and these are some options we've looked at:
posted by eseuss at 1:58 PM on June 11, 2013

How about a twist on the chukka, with Allen Edmonds distressed longtip Chukkamok?
posted by Giggilituffin at 2:26 PM on June 16, 2013

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