A few things from me. . .
As far as hair, fix it, dude!
When I was 20 years old, my hair was jet black, perfectly straight, and went down to my ass. I took REALLY good care of my hair, and girls loved it. I joined the military and off went all my hair.
My standard hair cut is now: #1 Fade, Boxed in the Back, leave some on the top.
Two examples of how this hairstyle can look:
https://www.pinterest.com/pin/295548794270799427/
Notice the longer hair on top. Chicks dig the fuck out of this hair style.
For a cleaner cut #1 fade boxed in the back, you can get more off the top, which looks like this:
https://s-media-cache-ak0.pinimg.com/23 ... 4b3565.jpg
You should take advice from people here and probably go to a stylist. But if you're too cheap for that, then you should really consider Crew Style cuts. Clean cut, responsible looking, something you can style around or just ignore.
As for your worry about using gel. I don't know what to tell you, except that gel can do wonders with your hair. Example:
https://s-media-cache-ak0.pinimg.com/73 ... ca034d.jpg
This is sexy right now. The retro look, clean cut, but bad-boyish. If you don't want a beard, fine; but don't ignore some mild sideburns coming to the bottom of your ear lobe. They put off a tough feel kind of.
And for shirts. Go to American Eagle and look at their long sleeve shirts. American Eagle is really good about having awesome looking shirts that go with a pair of jeans. Wal-Mart shirts don't fit worth a crap, they're either going to be too baggy, or too tight. American Eagle is typically generally tailored for Sexy.
You need to stand out, but not by looking goofy. This is just me, and how I stand out; but I love jewelry. This is just something about me personally, I like necklaces, I like bracelets, I like rings. I am really into turquoise, jade, and southwestern style jewelry. I do my own silversmithing, so my jewelry is almost all handmade by me. So I wear four rings, one of which has a blue turquoise stone, the other has a white buffalo turquoise stone, then two standard silver rings. I made all of these myself. I also wear a bright green jade bracelet, and sometimes I double up on bracelets on my right wrist, so Ill also have an elephant ivory bracelet.
For a necklace I wear a beautiful silver chain that I made myself, as well as a silver arrowhead shape pendant, inlaid with brown dinosaur bone, which I made myself.
On my left wrist I wear a Rolex Submariner. Now I don't wear the Rolex for bragging points, I NEVER mention the watch brand. It was a gift from my dad when I graduated basic training, he's had it since 1977, I also run a clock repair business & I'm learning watch repair; so I wear a Rolex. Here's the thing about the Submariner style watch, though; it goes with everything. It's not a super-fancy looking watch, but it cannot go unnoticed, either. It's silver in color, it's simple looking, but it is dressy to a degree. I wear mine all the time, I have for 8 years now. And before that I wore an off-brand submariner. I never take it off, even when I sleep.
Here's a picture of a Rolex Submariner:
http://www.adpost.com/classifieds/uploa ... 6498.1.jpg
It's unrealistic to expect someone to pay for a Rolex, but there is a solution.
For a submariner style watch, you can get one for a little over $100, and they are good quality, and look almost identical to a Rolex. It's called an Invicta Submariner.
http://pose.com.vn/images/baiviet/2013/ ... 560723.jpg
Almost identical.
The thing for me is that I like jewelry already, it makes me feel good about myself to wear jewelry, and as an added bonus it gets me attention while not begging for it. Here are links to the types of jewelry I wear:
http://www.polyvore.com/cgi/img-thing?. ... d=55586436
https://www.etsy.com/listing/150267266/ ... e-necklace
^^This is a necklace, but my bracelet is nearly identical. Except mine is prettier.
http://cdn.instructables.com/F0G/BRVY/G ... .LARGE.jpg
http://thumbs.dreamstime.com/z/turquois ... 203004.jpg
^^The one I wear most looks like the one on the right
http://www.ebay.com/itm/Navajo-Mens-Whi ... 1530947079
^^The one I made is almost identical to this design.
Also, I'm heavily tattooed, so that drags in attention without begging; so many people are tattooed now, it's become a norm.
I'm not saying you should go out and get a bunch of jewelry and tattoos. I'm just saying that this is what works for me and it's how I truly feel comfortable, and gives me confidence when I'm out. And you should find what works for you, while still being in style and attractive.
One added bonus for me, too, is since I have two kids, I *think* that wearing rings brings attention to the most important finger; my left index finger, which has no ring on it. Women will assume I'm taken when I have my kids with me, so I need to bring attention to my hands, so they notice that my marriage finger is bare. Who knows if it's true, it was just my thinking.