Choose the tomboy style you want to have. You get the outdoorsy, no-flair tomboy style (outdoor gear), the super sporty tomboy style (lots of sports clothing) or the street wear sporty style with graphic t-shirts and dog funk hats.
Start with shoes. This means no high heels or ballet flats, but there is more to it than this. Choose either skater shoes, or runners, with a masculine design, and preferably a brand such as converse, Reebok etc. Here is where you can play around a bit with funky colors, you do not necessarily have to choose black. Camouflage, red, dark green, and neon colors are still cool without being girly. If you don't like that you can wear wedge sneakers. You could also slip on some menswear-inspired shoes, like oxfords.
Choose your pants and shorts. Invest in some jeans, preferably on the loose side, choose a pair that are a little faded (light, not dark jeans), and distressed detailing is also a good option. Try to keep all of your clothes in a neutral color scheme, like black, gray, navy, and white. There should be no flares, no skinny jeans, no embroidery detailing, and no fading around butt or hip area. Definitely have sweatpants, but stay away from tight exercise pants and opt for looser fitting, drawstring sweatpants. A great place to find these is at college or high school gym wear stores, most sports stores only sell tight fitting ones. Also, invest in board shorts, or exercise (mesh shorts) Make sure they come almost to the knee, or a little longer, no tight fitting shorts (camouflage pants are another cool option).
Choose shirts, sweatshirts and jackets. Stick to the boy's section (or the girl's section). Even if the detailing is masculine in the boy's section, women's shirts are meant to conform to your curves which is okay but not wanted. A graphic t-shirt will give you more of a "street wear" look, otherwise solid, or simple design shirts are fine. You don't have to stay away from pink, most purples, and pastel colors; you can still be a tomboy and still like those colors because they're just colors, not defining of your gender. If you choose to wear a tank top, you don't have to wear a men's tank top but make sure it's not too tight. Get a hoodie from the boy's or girl's section, a kangaroo (or pullover) hoodie will give you the carefree outdoorsy look, and a graphic zip up hoodie from the boy's section will give you more of a street wear look. For a jacket, two-toned jackets are sporty, and usually have a masculine vibe, just stay away from pea coats, or anything to fashionable, or feminine.
Add some accessories. Just think: Would my brother/guy friend/boyfriend/dad/etc., wear this? If he wouldn't, don't buy it. For winter, tuques are great; do not wear berets, and stick with black-, or masculine-colored tuques, and simple, masculine-colored scarves, and chunky no-style, no-fur, winter boots. Great accessories would be: Outdoor broad-brimmed hats (the carefree outdoorsy tomboy). Baseball caps (sporty). Trucker caps (street wear). Avoid engineer hats, or military style hats, or berets. For winter, stick with tuques. Necklaces should have a thicker chain, preferably be silver, and have earthy detailing, rings are fine but should be dull and silver, stick to earthy jewelry, as opposed to glamorous jewelry. Earrings should be studs, and nose or eyebrow piercings are fine (more of a street wear look). Shop for wristbands, rubber slogan bracelets, rubber or cloth strap watches, and watches with large, chunky, faces. Bracelets should be very simple, bulky and masculine, or just a wristband.
Get the haircut. Do not get layers, if you choose to wear longer hair, and bangs should be cut straight across, and not side-swept. A ponytail, and a short haircut are also optional. You can pretty much choose what you want here, but avoid anything too fashionable (unless it is more a masculine fashion style) Ponytails should be not too low, and not too high.
Don't care. You should look as though you didn't put any effort into your appearance (or very little). However, avoid looking sloppy.
Choose swimsuits carefully. Don't go for a full on bikini. But you could go for something that exposes a bit because you are still a girl.
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