Reddit mentions of Sebago DOCKSIDES Men's Boat Shoes, Blue - Blue (Navy Nubuck), 10 UK(44.5 EU)

I actually had a friend ask something similar recently so I'm going to copy and paste what I sent him (From the line down). I also added a couple of bits that apply to you specifically, especially in the first point.

I'm not exactly a fashion master by any means but these are some rules I stick to and I get a lot of compliments on what I wear.

I'm European and generally, from what I've gathered from discussions with a few American friends, it's more expected of guys to take care with how they dress over here. So these are the basics I would suggest.

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• Find jeans that fit. If you think they're uncomfortable it's because either a) you're wearing the wrong size/cut, b) you're not wearing them for long enough. All new jeans are a bit stiff before you wear them in. Get jeans that are slim but not skinny. They should fit your form but still have some slack on them without being baggy. Like this -- it'll most likely be either skinny cut or slim cut, depending on how thick your legs are. I know you said you're against jeans but the fact is they're the perfect balance of being casual but not lazy looking like sweatpants. If you're REALLY REALLY against jeans then apply similar rules to chinos but chinos should be a tad looser
  
  
• If looking for shorts, don't get basketball shorts or sports shorts. It looks lazy. You want something like this - chino shorts work well. A braided belt goes well with chino shorts. The shorts should not go below the knee. On a side-note, I personally try to only wear trainer/ankle socks when I wear shorts.
  
  
• No graphic tees unless it's a basic basic design. Logos are fine, but no actual pictures of anything. No graphics that stand out.
  
  
• Get some button up shirts. Again they should be form fitting but not tight. Make sure you can comfortably roll up the sleeves (girls love it). If you're wearing a shirt with shorts, short sleeved shirts look better. If you're wearing trousers, rolled up long sleeved shirts are usually better than short sleeved ones. Checkered or plaid are good go-to designs but it's hard to go wrong with button up shirts, it's pretty obvious when a design is a no-go. I personally avoid leaving the shirt unbuttoned with a T-Shirt underneath but some people don't mind it. If you wear a T-shirt underneath for insulation purposes avoid a V neck
  
  
• Unless it's the summer where it's too hot, layering looks great and is practical in cold weather.
  
  
• Pick up some basic black and white T-shirts. Up to you if you prefer V neck but you need 2 or 3 simply because they're so versatile and can go with almost anything. And again, form fitting but not tight. In a basic T-shirt, the shoulder seam should sit roughly on the 'corner' of your shoulder. If it's further out than that it's probably too big - when the arms go too low and/or are baggy it isn't flattering. However, some T-shirts are just put together weirdly and the seam is further out. But in almost every case this is a solid rule
  
  
• Use striped T-shirts with caution, they're not flattering on everyone
  
  
• Learn what colours go with what. Personally I can intuitively see what works with what but if you can't just look at what colours compliment one another. Some general rules for colour: a) avoid having your lower and upper half in the same colour, unless it's jeans and a blue shirt which is usually fine as long as it's not the same shade of blue. b) avoid colours that would stand out in a crowd (really bright or neon). A bright red or green in particular stands out a lot
  
  
• Don't ignore the shoes. Often people have a good outfit on but the shoes don't match and it ruins it. Some blue or black low top converse or vans are EXTREMELY versatile and will go with almost any casual outfit. It's important you find something comfortable, though. Something like this would be good, although you obviously don't need to get any that expensive. For the winter I recommend Timberland boots. They look good and are EXTREMELY comfortable, and should last you years.
  
  
• Accessories aren't just for girls. A watch is good. Doesn't have to be an expensive metal thing, I use a retro one like this. Other options include wristbands (e.g. if you've been to a festival recently), any other wrist accessory that wouldn't look silly on a guy, scarves, hats, sunglasses
  
  
• Speaking of sunglasses, get a frame that matches your facial shape: http://i.imgur.com/kleafiE.jpg
  
  
• It's hard to go wrong with jumpers really, you can go baggy or fitting as long as the colour/pattern is reasonable and matches everything else. A grey hoodie (not zip-up) is fine in a casual setting and will go with pretty much anything. Bear in mind that unless you specifically follow that item's instructions, jumpers will usually shrink a fair bit in the wash. I always go one size bigger than I need for that reason.
  
  
• If there's a lot going on with what you're wearing above the waist, wear something very basic below the waist. And vice versa.
  
  
• If you're wearing a jacket, it's not something you just throw on on top of your outfit, it's a part of the outfit and so should match it. For that reason, get something that works with nearly anything like this
  
  
• Get a good haircut. Too much to really go into but as I'm sure you're aware undercuts are extremely popular right now. Make sure it's something that compliments the shape of your face and head.
  
  
• If you have a beard, keep it tidy and keep it groomed.
  
  Overall, it's easy to look good and like you care about your appearance without spending a ludicrous amount of money and without looking vain. If you see any expensive clothes you like the look of, you can EASILY find a cheaper version online. Nobody will be able to tell the difference unless they're into fashion and brands. A lot of people shy away from buying clothes online but as long as you know your basic measurements you'll be fine. However, I would recommend not buying off-brand shoes. It's one of the few items where buying off-brand is significantly worse in quality, durability and comfort.