How to Dress Case Studies Series, Pt. 1: Flings with Good Women

One of our students had a simple problem. He wore the same clothes to work, the bar, and dinner with a woman.

He had clean sneakers, dark jeans, and a loose black T-shirt. None of it was dirty. None of it fit well. The shirt hung off his chest. The jeans bunched at his shoes. His sneakers had a gray mark on the side.

He thought his clothes made him look relaxed. Women saw a man who had not taken care with his appearance.

He wanted to meet women who looked sweet and put together. He called them “good girls.” He meant women who had close friends, a steady job, and a soft style. They wore small gold hoops, clean makeup, dresses, cardigans, or fitted jeans.

His clothes sent the wrong message. He looked like he wanted to drink beer and stay out late. He did not look like a man who could take a woman to dinner without making her feel out of place.

We changed four things:

• His T-shirts fit his shoulders and stopped near the middle of his belt.
• His jeans became dark, straight, and clean at the hem.
• His sneakers were plain white leather.
• He added a watch and a light jacket that held its shape.

He did not start wearing a suit. He still looked like himself. He just looked like a man who could choose his clothes on purpose.

That shift matters. Women often judge your clothes before they hear your humor or learn your job. Your outfit gives her a quick answer to a basic question: “Will I feel comfortable standing next to him?”

For this kind of woman, loud clothes often create the wrong problem. A bright logo, ripped jeans, deep necklines, or a stack of rings can make you look like you need attention.

You want her to notice your face, your body, and how you carry yourself. Your clothes should help with that. They should not speak for you.

Start with fit.

A shirt should sit flat across your chest. The shoulder seam should land near the end of your shoulder. The sleeve should stop around the middle of your upper arm. If the shirt covers your whole backside, it is too long.

Your pants should follow your legs without squeezing them. The hem should touch the top of your shoe with one small fold. If the cloth piles up around your ankle, get the pants shortened.

Colors matter too. Navy, white, gray, black, olive, and light blue work well because they look clean without trying hard. These colors also make it easier to dress for dinner, drinks, or a woman’s home.

A simple outfit could be:

• A white Oxford shirt
• Dark blue jeans
• Brown leather boots
• A simple watch

Another could be:

• A gray knit polo
• Olive chinos
• Clean white sneakers
• A navy jacket

Both outfits show care. Neither one looks like you spent an hour in front of the mirror.

A fling still needs trust. A woman may want something short, but she does not want to wonder if you will act badly after two drinks.

Your clothes can show sex appeal without making you look unsafe.

Wear one item with a little edge. That could be a black leather belt, a fitted black shirt, boots, or a dark jacket. Keep the rest simple.

For example, wear black jeans with a white shirt and brown boots. The boots add weight to the outfit. The white shirt keeps you from looking like you are trying to play a tough role.

You can also show your body through fit. A shirt that follows your chest and arms will do more for you than a shirt with a large graphic. If you lift weights, do not wear a shirt two sizes too small. Your sleeves should touch your arms without cutting into them.

Skip clothes that make a woman work to feel safe around you:

• Shirts with violent images
• Pants hanging below your waist
• Heavy chains
• Dirty work boots at a nice bar
• Clothing covered in brand names
• Strong cologne that fills the room

One guy I coached wore a skull T-shirt on nearly every night out. He said it made him look dangerous. It made women ask their friends if he was trouble.

He switched to a fitted black henley, dark jeans, and clean boots. He still looked masculine. He also looked like he could listen when a woman spoke.

That is a better kind of edge.

Your outfit has to fit the room. A polished outfit at a dive bar can look stiff. A sloppy outfit at a wine bar can shut you out before you speak.

Before you leave, check the place online. Look at the photos. Notice what the men wear. Then dress one level sharper than the average man in the room.

At a casual bar, wear dark jeans, a fitted shirt, and clean sneakers or boots. At a restaurant, wear chinos, a tucked shirt, and leather shoes. At a house party, wear jeans, a knit shirt, and a light jacket.

Do not wear the same full outfit in every setting.

One student used to wear a blazer over a graphic T-shirt at every bar. The jacket did not match the shirt. The mix made him look like he had dressed in the dark.

We changed the jacket to a plain navy overshirt. It worked with his jeans, and he could take it off without ruining the outfit.

Also check the small details before you leave:

• Trim your nails.
• Clean your shoes.
• Remove pet hair from your clothes.
• Empty your pockets.
• Use a small amount of cologne.
• Wear a fresh shirt.

A woman may not praise your clean collar. She will still notice it.

If you invite her back to your place, keep your clothes simple and clean. Do not change into sweatpants with holes or a shirt you wore to sleep.

Wear a clean T-shirt, fitted lounge pants, or clean shorts. Keep a fresh towel in the bathroom. Put clean sheets on the bed. Empty the trash. Your room should show that you expected another person to enter it.

This does not mean building a fake luxury life. A clean room and clean clothes beat expensive furniture covered in dust.

One student had a good outfit but took women to a bedroom with dirty sheets and old food on the floor. His clothes created interest. His room killed it.

Women do not separate your clothes from the rest of your life. They look at how you care for your body, your room, and the space she has to share with you.

Dress like a man who enjoys sex and respects the woman standing in front of him. That combination looks better than any loud outfit.