| I am also on the shorter side (5'-6") and a similar build (muscular/stocky) so I can give you some pointers. Us short guys need to use our appearance and our to overcome women's natural inclination to snub short guys in favor of taller men. You're a handsome guy, you looked well groomed and you appear comfortable in your skin. Right out of the gate you've got a huge advantage. Overall my impression is that you have an unmemorable and boyish style. If you were in a bar you would blend in with a sea of other unmemorable guys and a hot babe might tease you for looking like a young kid. And being on the shorter side, you might not get noticed at all. Your look is fine for the local pub, would also not be socially acceptable for a higher class locale, which frankly is where you're going to get access to the hottest women. When you're planning your wardrobe, think about the classiest joint you could go to (short of a wedding or job interview) and dress so that have a slightly casual style but wouldn't look out of place there. You need to take your outer game up about 2 notches.
Most off-the-rack men's shirts are not tailored for us to wear untucked successfully. The tails and sleeves are too long because the shirt is tailored for an average guy who is 2-3" taller than us. If you go for a button up shirt, go to a higher end retailer where the shirts are made to size. You look like about a 15" collar x 30-31 arm. What they call "Athletic cut" in the states is more form fitting around the torso, but sometimes those can pucker on us short stocky guys so make sure the shirt fits well with no pucker. If you're in UK/Aus. I'm not sure how they size shirts over there.
This may sound kind of weird sounding, but next time you're in a department store, go to the Youth section and try to find some XL shirts that are cool looking and try them on. Kids today are a lot bigger than they used to be and you may find some interesting styles. You'll find that the tails are shorter so they look better untucked (an untucked shirt should not come down past your groin or any outer coat you might wear - shoot for about even with your jeans pockets). The sleeves should fit well without bunching up at the cuff. If you don't want the formal look of a buttoned shirt sleeve, open them up and do a single turn upward. NEVER fold them under unless you're really striving for the redneck/NASCAR look. It's fine to wear short sleeves when the weather permits, but don't try to pull off intentionally showing a lot of skin unless you truly have a great tan and/or muscle tone in your arms to do it. Patterns/lines are also good - vertical lines are obviously better than horizontal for our stature. Create some visual interest on your chest without making it look like the art department threw up on you. Lose the white tee shirt. Get a vee neck tee shirt, go without entirely, or if you must, find one that's got some color. You're a sexual object, right? Show some chest skin to prove it, and having a bit of chest showing helps elongate the region of your body from your hair line down to the first button. If you have some chest hair, all the better. Show it off a bit. Never more than two buttons open on a shirt unless you're going for the hairy old Greek guy look.
Your jeans are fine. I can't see what the top part looks like. I am partial to wide belts with big buckles. Skinny jeans don't fit our frames well, but relaxed fit can look like you're swimming inside, depending on the cut so choose wisely. You might want to get those particular jeans shortened a little bit - they're hanging a little low. Us short guys need to have pants that go straight to the ground so we look a little taller. Pants that bunch up at the shoes make us look more like hobbits. Just because that's an accepted "style" doesn't mean it needs to be your style.
You need to accessorize more. I'd like to see your sportcoat or an over coat or something. Look for some pendants and jewelry. Check in consignment stores or places like charity shops (Goodwill/Salvation Army if they have those in your area). I found an awesome Calvin Klein suede coat that is like a slightly heavier weight but insulated sportcoat in an upscale consignment shop - it fit like a glove and only cost about US$20. My ex-wife threw out my old motorcycle leather which I miss desperately. A stylish but unique hat might be good too. Find some peacocking items and lock in props.
As for footwear - I have two pairs of boots that are my standards for going out. One is a oxblood cowboy boot and the other is more of a blonde/tan fashion boot with a zipper on the inside. Both have easily a 2" heel so that's a great way to get some extra height without going to the extreme of platform shoes. These also came from a consignment shop, not a lot of money invested. With tall boots you can get away with slightly longer pants (in fact it's preferable) but you still don't want them to gather up at the bottom. Nix on the loafers with no socks. Only women look good showing off bare ankles.
Important tip about boots - make sure you don't wear skinny jeans with cowboy boots. If the top of the boot is visible through the pantleg, then the boot is too flared for that jean, or the jeans are too tight for that boot. Boots with tall heels force you to walk a little more slowly, which is a huge help. You walk with a bit of swagger which chicks love and they make noise when you walk, which can get you some attention (not in a club but pretty much everywhere else). As a shorter person, NEVER tuck your pants inside boots. You want your legs to look as long and straight as possible.
Don't sweat your waist line too much. I got laid the most when I was 34" waist. I'm 35" right now and a lot bulkier because of some serious weight lifting I did in my 20s. Of course being trim and healthy is always good but it's not essential to being attractive. You don't show it in your face. Just don't shoot yourself in the foot by wearing skin tight clothes where a little tuck of chub would be noticeable. Keep it easy breezy without looking like you're wearing a tent.
Don't take this the wrong way but you have a slightly pouty face that women can see as boyish. That might work on cougars but if you want to get some hot women your age, consider some facial hair of some kind (well groomed and limited). No Grizzly Adams here, go for a small goatee van dyke. If you were a bit thinner your facial features look like they'd be severe enough to go clean shaven, but for your frame I'd definitely encourage a bit of fuzz somewhere. Even a soul patch would do you well. Your hair looks OK - spike is definitely important. Consider some highlights to add some visual interest to your thick mass of dark hair. Bring the attention away from your widow's peak so you don't have that Eddie Munster look about you. Keep the hair on the sides of your head cropped tight it will help make your face appear less round, which is boyish trait. I cut my own hair with clippers and I always use a #2 and 3 on the side, tapered up a #7 on top with slightly longer bangs that I spike up. Tell this to your barber or stylist and he or she will know what I'm talking about.
I hope all this helps.
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CHAT
