[Links to pictured products would be included in an actual report, which probably would be much longer than this]
Mr. Williams, you have communicated a desire for comfortable, casual attire on your personal time. From your submitted pictures, it is clear that you look younger than your years, and you have mentioned looking older as a goal. A summary of our analysis is that your appearance is pleasant, but ineffective, as is.
You seem to know to avoid bad color combinations, inappropriate clothing, and a number of other common traps. Yet nothing is especially positive. What you wear could be bought almost anywhere and worn on almost anyone, including people younger than you. You look as though you make clothing choices primarily on convenience and the need to not offend. Where is the personality? You aren't particularly physically distinctive; you need to make a conscious effort to look better and be worthy of notice from others. The good news is that a stronger presence can be achieved, in making you resemble more of an ambitious, hard-working, yet approachable man in your personal life, all while not spending a lot of time and money on clothing and stylings.
Hair and Skin
A more 'squared', medium-length hairstyle could lessen the roundness of your face and enhance maturity. This effect can be created by any competent barber. If you desire something more elaborate and trendy, you should consult a hair stylist who has many male clients. Whomever you choose should trim your unruly eyebrows, which are too bushy and too long. With your urban location and a telephone directory, help should not be hard to find.
Also, more sun exposure, of the safe, sunscreen-involved, late-morning/early-evening variety, would benefit your appearance. Use a lotion moisturizer immediately after twice-daily washing (and gently drying) your face, to combat the combination skin. Since we can see some razor nicks on your face, try to shave more carefully - moisten your skin with hot water and/or shaving cream before you start the routine. If that does not work, try a different type of razor.
The strategy we advise is to subtly and gradually improve your wardrobe. The white tee-shirts, province of students, should be the first items to be relegated to unimportant occasions. You should purchase some quality t-shirts and pullovers (but not of the tight-fitting variety, for now). You will find good examples of this at Banana Republic. Also, judging by the plethora of unadorned solids in the pictures you submitted, you need more visual variety. Buying shirts with design details such as small, square pockets, sturdy buttons, and subtle horizontal stripes will accomplish this and add maturity and authority. In cooler weather, neatly layering quality v-necks and sweaters over your holdover tee shirts (or new shirts) should add size and convey sophistication. In all seasons, materials including linen and silk will add class to the impression you make, while also increasing physical comfort and adding variety. Make sure the lengths of these shirts, when worn un-tucked, do not extend far past your waist. You already own a few blazers; wear them for special semi-formal occasions (such as dates), with a quality pullover and pants or jeans.
What about pants? The stores you probably prefer are full of them, but avoid purchasing fashion-forwards jeans, such as the 'vintage' or distressed kind. Stick to blue and black jeans of the regular fit. Consider adding some corduroys, twill pants, and traditional cargo pants to your collection. Also, a pair of designer plain-front black pants, such as those found at Kenneth Cole, is great for dates and other dressy occasions. You own so few pants that you should buy a pair or two immediately. Because of your low clothing budget, wait for sales - great discounts are often found online - to buy some others.
Utilize more color and contrast in your outfits to liven your impression. An example is a sky blue shirt (to emphasize the blue eyes) with dark blue jeans. Blue and brown should be a major part of your wardrobe, but do not wear solid-color brown and blue together unless you are sure the particular shades look compatible. A third color should be part of most of your outfits. See our "Color Can Be Masculine" article for more details. Also, Mr. Williams, we can tell that you aren't as careful with clothing care as you should be. Smooth out wrinkles after laundering and when checking yourself in the mirror.
Lose the cheap-looking watch. It makes you look like an overgrown kid. Wear analog all-metallic or metal-with-leather pieces only. A Rolex or other very expensive one would be inconsistent with the rest of your image.
Make sure your outdoor jackets are age-appropriate and good quality. A black leather jacket with brown trim would nicely pick up your brown hair and boost your masculinity.
Yours look clean, but white sneakers get soiled too easily and draw too much attention to the feet. They also convey youth. When you need to wear sneaks, wear them in black or gray, in the New Balance brand for maximum comfort. For other situations, get into the habit of wearing sneaker-shoes or casual shoes, usually in brown, but some evenings in black, in a water-resistant leather or realistic imitation leather that would stand up to your rainy locale. No boxy shoes, because they would look out of scale with your rather small frame. You should find scores of suitable shoes at your local shoe (not sporting-goods) store. If not, look at our Resources section for an online shoe retailer, but be aware that you might find that your purchase does not fit you right and will have to be taken to a shoe store for modifications.
To better fit your clothes and remove some of the babyishness from your face, Mr. Williams, we recommend improving your diet and starting an exercise routine. We can tell you that regular weightlifting and aerobic exercise, along with a diet higher in protein and lower in fat and low in salt, will help to give you a more adult-like upper body and face, as well improve your forward-neck problem. The process is going to take at least several months. Your big-city location should make it relatively easy to find both a certified trainer and certified nutritionist who can give you more details.
Having your chipped tooth fixed is a good idea, if you can afford the few hundred dollars it would cost. If you want to go through with having your teeth whitened, you should have the repair done first, for whiter teeth would highlight the flaw. Regular whitening toothpastes produce almost no improvement, as you might have already discovered. You can try an over-the-counter whitening treatment, but the most effective method involves going to a cosmetic dentist. This would also cost several hundred dollars, slightly more for the superior laser bleaching.
We at Gentleman's Best Friend Image Consulting Services wish you luck in reaping the benefits of your new image.