How to Dress Like a Guy

Co-authored by Joanne Gruber

Last Updated: May 3, 2020 References

Dressing like a guy doesn't have to be difficult, whether you are a woman trying to dress like a guy or a guy who is trying to achieve a more masculine look. Paying attention to the shape, cut, and quality of your clothing can help you achieve a more masculine look

Part 1

Part 1 of 3:

Dressing Like a Guy

1
Find casual pants with a masculine fit. Casual pants that fit well are a staple in a male wardrobe, as they can be worn in most everyday situations. ^{[1]
X
Research source}
- Jeans are the most versatile pant. They should be worn an inch or two lower on the waist than chinos or corduroys, about three to four inches below your navel. Jeans should have a consistent fit throughout the leg. Avoid jeans that are too tight in the thigh and loose under the knee. Slim-style jeans flatter most body types.
- Sweatpants are the most casual pant, usually worn in athletic or relaxing situations. When wearing sweatpants out in public, try brands that also make formal pants; they're more likely to fit slimmer and look better than the typical gym sweatpants found in discount stores. Pair sweatpants with other well-fitting clothes and a pair of high-end sneakers to avoid looking too aloof. ^{[2]
  X
  Research source}
EXPERT TIP

Joanne Gruber
Professional Stylist
Joanne Gruber is the owner of The Closet Stylist, a personal style service combining wardrobe editing with organization. She has worked in the fashion and style industries for over 10 years.

Joanne Gruber
Professional Stylist

Choose androgynous pieces. Stylist Joanne Gruber recommends: "Try wearing a pair of chinos, a T-shirt, a blazer, and white sneakers for a casual masculine look. If you're wearing jeans, you could toss on an oversized flannel or parka. There are even brands that sell women's clothes cut to look like a men's clothes, like flannels and leather jackets. You can also find great belts and watches in the men's section, even if your style is more feminine."
2
Choose the right fit for dress pants. Formal pants are important for presenting a clean, conservative look- perfect for the office and special events.
- Suit pants and dress trousers are the most formal pant option. The top of the pants should come to the top of your hip bone. They should fit well enough in the waist that you don't need a belt, but drape more loosely over the legs. Avoid wearing pleated pants, as they can add the illusion of extra weight, especially in the seat.
- Chinos and corduroys offer a more casual look than suit pants, but can still be worn in most professional environments. These should fit slimmer than suit pants and worn an inch or two lower on the waist. If you're wearing chinos in a conservative setting, opt for a slightly looser fit. If wearing casually, you can size them slimmer. You can tell when these pants are too tight if the pockets don't lay flat against the pants, creating "pocket flares." When shopping for chinos, keep in mind that the waist and seat tend to stretch with wear.
Advertisement
3
Wear casual shirts that fit well. Casual shirts, despite their informality, can look great when sized and worn correctly. They can be worn with chinos, jeans, or sweatpants.
- T-shirts and long-sleeved shirts are more casual than button-ups and sweaters. They should fit looser around the neck. If a shirt has a V-neck, the cut of the V should go no deeper than your sternum. A t-shirt or long-sleeved shirt should have a slim fit through the torso, a little looser than a button-up. The shirt should be long enough to cover the belt loops of your pants without going past the pants zipper. Longer, looser T-shirts are best for a laid-back vibe, while more fitted, shorter T-shirts look sleeker. Many T-shirts and long-sleeved shirts are made primarily of cotton, which shrinks easily when washed. Size up or hang dry your shirts to avoid shrinkage.
- Undershirts should be worn under other kinds of shirts. They should fit tighter than a T-shirt, and have the same kind of collar as the shirt you're wearing over it. Choose a color like gray that will match most kinds of shirts and be inconspicuous under other clothing.
4
Wear the right kind of dress shirt to complete a formal look. Dress shirts are another necessary staple in the male wardrobe. A well-fitted dress shirt rounds off an outfit to create a crisp, professional look.^{[3]
X
Research source}
- Button-up shirts can be worn for professional and casual situations. The collar of a button-up shirt should fit as closely to the neck without constricting it. The sleeves should fit well, without being too tight or too loose. The shirt cuff should come to where your wrist meets your hand. The body of the shirt should fit closely to your torso, without being skin-tight. A button-up should come down just past the belt loops in length. They should be worn tucked in to pants for a refined look; however, they can be worn untucked with jeans or chinos in a more informal climate.
- Sweaters can also be worn in both formal and informal settings. They should fit slim throughout the body. Thin sweaters can fit tighter while chunky sweaters can fit a little looser. Thin sweaters should be worn to your belt loops; thicker sweaters and cardigans can be worn long. Crew neck sweaters should allow plenty of room for your neck and a collared shirt underneath. The neckline ofV-neck sweaters should dip down no further than the middle of your sternum. Turtleneck sweaters should fit tighter in the neck, while shawl neck sweaters are loose in the neck. No one kind of sweater is considered more or less formal; they all can be worn in a variety of situations.^{[4]
  X
  Research source}
5
Dress for your body type. Different clothes flatter different body types and have ways of making you look more masculine.^{[5]
X
Research source}^{[6]
X
Research source}
- To hide wider hips and thighs, wear tapered pants.
- To hide a bigger chest, wear tops with prints and asymmetrical patterns.
- To look taller and thinner, wear vertical stripes.
- To look less lanky, wear horizontal stripes.
- To slim your waistline, wear a belt.
- To look thinner, wear monochromatic colors.
- No matter the body type, buying clothes that fit properly will ensure you look your best in any men's outfit.
6
Complete a formal outfit with the right dress shoes. Shoes can make or break an outfit, and are especially important to pair correctly with dress clothes.^{[7]
X
Research source}
- Oxfords- Lace-up shoes worn below the ankle, usually made of leather. Work best with a two-piece suit.
- Loafers-Slip-on shoes without laces, often made of leather. Less formal than oxfords. Can be worn with a suit or with more casual pants.
- Dress Boots- Usually made of leather and come in a variety of styles. Come up high on the ankle and lace up. Should not be worn with a suit, but can be worn with chinos, corduroys, or jeans.
7
Find a casual shoe that meets your needs. There is a wide range of casual men's footwear options, varying in comfort and functionality.
- Saddle Shoes- Similar to Oxfords, but have a layer of leather over the instep of the shoes, making them two-toned. Should not be worn with a suit, but can be worn with any kind of pants.
- Top-Siders- Also called "boat shoes." Have a moccasin-style and thick rubber bottom. Can be worn with or without socks and work best with chinos, corduroys, jeans, or shorts. Should only be worn in the summer.
- Canvas Shoes- Usually describes sneakers with a canvas body and rubber sole. Can be low on the ankle or come up high over the ankle. Able to be worn with chinos, jeans, or shorts. Converse All-Star sneakers are the stereotypical example.
- Casual Loafers- Slip-on shoe, distinctive from the dressy version by a heavy, rubber sole. Can be worn with or without socks, with chinos, jeans, or shorts.
- Sandals- Open-toed shoes that protect the bottom of the foot while allowing open circulation on the top and sides. Flip-flops are a popular type of sandals. Work best with chinos, jeans, and shorts, and are most appropriate in warm weather.
- Athletic Shoes- Sneakers that are usually made entirely of rubber, especially on the sole. Should be worn mostly with activewear and only in athletic and very casual instances.
- Work Boots- Heavy-duty, solidly-made boots made to withstand long hours working outside. Commonly referred to as "construction" boots. Should only be worn during labored tasks such as yard work or moving heavy items.
- Hiking Boots- Come up high to support the ankle, are well-cushioned, and lightweight. These are the best footwear for outdoor sporting events in rough terrain.
8
Find shoes in your size. Buy men's shoes in a size and a half smaller than what you wear in women's shoes. For example, if you're typically a size 7 in women's shoes, try a 5.5 in men's shoes.^{[8]
X
Research source}

Part 2

Part 2 of 3:

Accessorizing Like a Guy

1
Don a hat. Hats are a great way to hide your hair and add to your outfit. Different occasions and environments call for different types of hats.^{[9]
X
Research source}
- A baseball cap is commonly worn among men, and generally considered to be informal. It can make a specific statement about who you are if it contains a sports team logo or company name.
- A fedora is a great way to complete a formal outfit.
- A beanie is an informal hat, better for colder weather
- A Panama hat is a popular option for a laid-back place- perfect for a vacation. .
- A cowboy hat works well in a ranch setting or somewhere with a Southwestern feel.
2
Put on a belt. Belts serve the functional purpose of keeping pants in place, as well as tying together the top and bottom half of an outfit. The belt you wear should match in formality with your outfit. Try a leather belt for more formal clothing and a canvas belt for more casual threads ^{[10]
X
Research source}.
3
Don't wear much jewelry. Generally speaking, men don't wear a lot of jewelry. If you want to wear jewelry, keep it simple. Often a singular piece, like a watch or a chain, will do. ^{[11]
X
Research source}.

Part 3

Part 3 of 3:

Styling Your Hair Like a Guy

1
Wear your hair short. Most men prefer shorter hairstyles. If you're not ready to give up your long, feminine locks, try tying them back in a ponytail or sporting a "man bun." If you want to cut your hair short, familiarize yourself with the names of different men's hairstyles before getting it cut.^{[12]
X
Research source}
- Taper Cut- A short haircut with the sides and back of the head cut progressively shorter down toward the neck.
- Bowl Cut- Longer hair around the top of the head, shorter hair around the lower part of the head, with little or no blending in between the two lengths. Looks like someone placed a bowl on your head and simply cut around it.
- Brush Cut- Short, tapered hair around the sides of the head, uniform in length at the top of the head. Hair at the top of the head is styled straight up to resemble the bristles of a brush.
- Business Man's Cut- Generic term for a shorter (but not too short), conservative haircut, appropriate for the office. Hair is short and tapered around the sides and longer at the top to allow for a part.
- Caesar Cut- Back and sides are tapered, while hair at the top of the head is layered one to two inches in length. The top hair is combed forward giving the effect of bangs.
- Crew Cut- Very short cut that is tapered on the back and sides and top of the head.
- Fade- Extremely tapered cut, with hair on the sides and back cut very close to the head and tapered upward to a longer length at the top of the head.
- Flat Top- Back and sides are very tapered, while hair on the top is cut to stand straight up.
2
Use men's hairstyling products. There are several different kinds of hairstyling products that can help to maintain a masculine hairstyle. Each product is used to achieve a specific look.^{[13]
X
Research source}
- Pomade- Use on shorter styles, to create texture.
- Wax- Use to add shine.
- Mud- Use on longer styles, to create a "disheveled" look.
- Cream- Use to control frizz.
- Gel- Use for a strong hold or to create a "wet" look.
- Hairspray- Use to add volume and greater control to hair.
3
Cut your neck hair and sideburns. With shorter hairstyles, men need to be more conscious of the hair on the backs of their necks and the way their sideburns look. They have less hair to hide under than most women do. Be sure to talk to your barber about how you want your neck hair and sideburns cut and shaped.

Community Q&A

Question

How do I hide my chest?

Community Answer

You can purchase a chest binder, or wear looser-fitting shirts. Crossing your arms in social situations can help camouflage a larger chest.
Question

What if my parents won't let me wear boys' clothing?

Community Answer

The "boyfriend" style is what I am working with for my granddaughter, so I would try that. T-shirts and jeans, blazers, vests, button-up/"dress shirts", loafers, etc. are all made in women's clothing. As the tips that are given in the original article say, it's all about fit, so find those clothes in women's styles and see what you can come up with!
Question

What if my hair is longer than shoulder length but I don't want to give up my locks yet? What do I do?

Community Answer

Maybe try hiding it under a beanie or a hoodie or a cap, but make the ends of your hair stick out so it looks like you have short hair and haven't just shoved it all in your hat.