hi - I was hoping for some advice/opinions on winter shoe shopping. It's been a long time since I looked into buying boots, and checking out all the options online I am a bit overwhelmed. I know what I like, but I am not sure that they are something that is actually worn normally. Getting what you like is important I know, but in this situation I am trying to have some style.

For instance, on the men's section on a major shoe site they have UGG boots. Now, I like these boots - but I've never seen another guy actually wearing them in my limited experience of paying attention to other people's feet. I also fear they may look strange with jeans. anyone have experience?

It seems like the general boot options break down to hiking style boots, doc marten types, and dressier styles. What kind of boots does one normally wear with just jeans or cargo pants? Or are boots a no-no for cargo pants?

I like the look of the hiking style boots but fear they may be the wrong type to wear out with a nice sweater or jacket.

My last question is about sizing. if I get a size too big to compensate for appearance of smaller feet size am I going to just be horribly uncomfortable?

thanks for any style advice, I am clueless

I'm rather clueless myself.  I suspect our resident fashion guru (insideontheoutside) will be able to help you.

I haven't seen any guy wear ugg boots either.  Not sure where you live, but most guys around (Deep South USA) here wear cowboy boots, hiking boots, or work boots.  Some dress boots with suits and the like.

As for the size, get what's comfortable to you.  From what I remember, boot sizes can be different from regular shoe sizes.  Just like any other shoe, try several pairs on and walk around in them.  Try not to worry about what size you get, focus on getting a size that fits right for you.

If I see a guy wearing Ugg boots I feel like laughing, why? (and note, I live in the Netherlands, other countries may differ) Ugg boots were designed for men but women ended up really liking them and now about 9 out of 10 of the ladies here own at least one pair of these (rather expensive) slipper like boots. True, I don't like Uggs, but Uggs on men look wrong to me (and a lot of people I know). We sort of consider them to be slippers you can wear all day and the few ladies that I heard about them say that they are a bit, 'but they're so nice and comfy and warm!'.

Then.. I consider hiking boots to be a good random boot. Steady, comfy, warm and it looks good most of the time. Just make sure you get the light hill walking type and not the heavy hiking type, wearing these daily will make some muscles 'lazy'.

And size, if one would pay attention, I think one could notice in the way someone walks if their shoes might be too big. Make sure they're comfortable, I think it might 'hurt' you in the long run if you walk on oversized shoes daily. Know that you might take half a size bigger if you put insoles in the shoe, but it's not as good as a natural fit.

Also, since you're shopping online. Sizes can be different not only shoes and boots, but also each brand. My converse, skate/sneakers, heavy hiking boots and another set of boots all have a different size. (more or less) Best to buy them in the shops ór, try the brand in a shop and buy online.

it pretty much depends on where you live and so.
when I where in Japan I found shoes who in my country would be considered for women in the male section and so.

I had no idea what ugg boots were so I googled. Had no clue that was what those things were called...but I think they look horribly silly on anyone who decides to wear them, lol.

I don't think I've ever seen a guy wear them, but if you like them you shouldn't let that stop you.

I pretty much wear my hiking boots everywhere, and I mainly wear jeans, cargos and camos. As far as how "formal" you can go with them, it depends on the colour. Mine are black, so I they pretty much are unnoticeable in most situations. Don't know what you mean by nice sweater or jacket, but I assume unless you're going to go out in totally formal wear or slacks or something, you should be fine. If you want something "nicer" I guess go for docs.

As for size, I have no idea. I usually get shoes that fit

Uggs are for teen girls over here in England and they quickly crush down, distort and roll over and make walking difficulty and probly ruin the feet long term.   
there should be lots of low heel, plain dark shiny boots around for day and evening wear with jeans or trousers.  but then the lighter hiking or work boots are OK too.
what is best for any newbie TS is things that blend in rather than draw attention.

I don't know about where you live, but what about military boots. I think you can buy some from the Army surplus store. I want to get some T.U.K creepers myself.

hmmm well ill give you some personal opinions

if you are a masculine type of guy who likes football and beer and dosent really care about his apearence some regulare brown work boots would suit you.

i really like timberlands new earthkeeper line of boots because they are masculine without looking to huge and clunky. these are the ones i like the most and ill probably get them when it starts snowing in NY. these boots go with everything they are slim enough to wear with jeans or maybe even khakis but they are masculine enough to wear with cargos.

http://shop.timberland.com/product/index.jsp?productId=4207926

i also really like these but i wouldnt wear cargo pants with them.
http://shop.timberland.com/product/index.jsp?productId=12262903

there are also these boots called chukka style boots that are casual dressyer mens boots that look nice with jeans and a sweater or a non althletic type jacket.

talking sizes im a true mens 8-8.5 but i wear a 8.5-9 i find if i go any bigger they look like clown shoes (because i have really skinny legs) and they are a lot less comfortable.

I like Doc Martens. They're really expensive and no longer even made well, but they turn up in thrift shops occasionally, and I think they look alright for most occasions. I can't wear mine anymore because they don't fit over a brace I use, but I'll probably go back to them when I can. They're more comfortable (to me) than any military boots or work boots. I keep a pair of 5-eye short ones separate and in good condition for when I need to dress more nicely.

Lately I actually wear a pair of sneakers that I dislike a lot. I should probably do something about that at some point.

I've only very rarely seen a guy wearing uggs, but I have seen plenty wearing ugg slippers with baggy sweatpants or something. 

In my opinion Uggs look horrible on anyone, man or woman. To me they say 'i am too lazy to spend the time lacing up an actual boot'. Also I'm assuming they are not good for wet winter weather.

Something like this would probably look good for whatever you're wearing:
http://www.zappos.com/rockport-break-trail-chukka-caramel-plaid

I've never had Rockports but they're all my dad has worn for years and supposed to be really comfortable. Chukka boots are kind of 'in style' thing right now, if you care about that kind of stuff.

As far as shoe size goes, you could probably get away with half a size bigger or maybe wear an extra pair of socks, but I think wearing something too big would just give you blisters. If you want to order them online you can always go to Sears and try a few different sizes on to see how they feel. And I dunno if you're on T/planning on going on T but my foot went up half a size (from gaining weight I guess) and I had to buy new shoes, now I'm wishing that I had bought them a whole size bigger because in case they grow again.

i have my cow boy boots on all the time.   ..... unless i am working in a a stall that is in need of major attention, then i have hiking boots on, more stability for you ankles and wont slip as fast, witch is great when you are in a $h!t filled stall but some how i dont think you will be  but i do wear cowboy boots with everything even cargo!

Wearing Uggs as a guy will alarm everyone's gaydar around you... It looks meh, but goes with jeans. Not with cargos at all.
Get Wolverines, Red Wings or Timberlands. You can wear these with pretty much everything.

Wolverine 1000 Mile


Red Wing Chukka


If you like sneakers more you can try Nike's AF 1 Hiking

or their new Air Force Duckboot which I don't like lol

Google image search for "Winter hiking boots."   I personally love them.  I think they go great with jeans. 
Here is a pair similar to mine,

Thank you all very much for the advice and for saving me from myself and my desire for UGGs

So many nice boots linked too.

I think I am going with these, though I really like the chukka style boots too:



I figure they will work with everything, and hopefully they will be comfortable. I will just get the size I normally wear. My mention of the sizing thing is because I normally wear sneakers exactly like this:



In the shoes above, I feel like my feet look really tiny under pants, though that is probably partially just in my head. The bulkiness of the boots should help, I hope. I agree getting shoes too big would probably end in disaster.