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How To Dress To Attract The Kind Of Woman You Want To Date.

I’ve been reading this immaculate masterpiece of a book called, How To Dress For Success, by the one and only, Edith Head. She has a whole chapter dedicated to women called “How To Dress To Get A Man And Keep Him”, which I’m completely obsessed with. Of course, I took copious notes. I love learning from the greats of the fashion industry, past and present. Edith Head is said to be the greatest costume designer of all time. She dressed the most famous actors and actresses in their most noteworthy roles throughout the Golden Age of Hollywood. She also designed much of her clients personal wardrobes, making her Hollywood’s first celebrity stylist before it was a sought-after profession. I’m not in love with how she supposedly “borrowed” sketches from her fellow art school students to get the job with Paramount Pictures. I’m not sure if she asked for them, but I certainly hope so. In the chapter, How To Dress To Get And Keep A Man, she speaks to women, but since I’m also a certified menswear personal stylist, and I also offer men’s relationship mentoring, I thought it would be helpful to tailor this post to the gentlemen. When I’m quoting her, I’ll be using the word men/man. But I’ll be breaking it down for men as a how-to guide for dressing to get and keep the woman of your dreams.

The Different Motivators Behind Dressing Men vs. Women. 

Dressing men is very different from dressing women. Psychologically, they have different motives when it comes to personal style. For example, women tend to be more insecure about their bodies. Not all women, but generally speaking, the goal when dressing women is to visually achieve the hourglass shape. Men, on the other hand, are motivated to choose his clothes by how the world perceives him, his role, and his position in the world. The male ego is very much invested in getting people’s respect. When a man leaves the house, he’s not thinking about how his body looks in his jeans. He’s thinking, “do these jeans make me look badass?” He’s thinking about how his clothes are going to get him the respect he’s going for when he goes into the workplace, or on a date. Men want to be well-received whether it’s on a job interview, or on a date.

Dressing To Get And Keep A Woman. 

Edith Head knows what she’s doing. I read this book, and told all of my actively dating, single friends about it. Essentially, Head’s tips work whether you’re dressing for a man, or a woman. You just flip the script. For this blog post, I’m gonna flip it for men who want to attract and keep their dream woman. If you’re reading this, and are looking for a same-sex relationship, or any other sexuality, just swap the gender pronoun for the one that works for you. This post, will be written for a straight narrative, but these invaluable tips can be applied to any masculine/feminine energy in any relationship, regardless of sexuality.

Gaining Clarity On The Type Of Woman You Want To Date. 

There’s a common theme I see in many of my clients regardless of gender. Both women and men who have worked with me face the common style struggle of not knowing how to put outfits together, how to tell if an outfit looks good on them, and how they don’t always know what they like when they see it. They run into the same problem with finding clothes that fit. Obviously, there’s a tactical solution here, but not being able to tell if something fits also has a deeper psychological correlation. A closet full of clothes that don’t fit often translates to dating a lot of people who also don’t fit. I wrote a blog post on this called: Good Fit vs. Bad Fit: How To Tell If A Piece Looks Good On You. In this post, I share why not wearing clothes that fit or feel like you creates cognitive dissonance. Check it out, and try it on for size. Pun intended. This post was written to bring clarity to the type of romantic relationship and woman that best suits you. Because chances are, the man who is wearing clothes that don’t fit well is also dating women who don’t fit. So, the first step in getting the right woman for you, and keeping her, is getting clarity on what kind of woman you want in your life, and then dressing to attract such a woman.

The Five Dressing Types For Men and Women. 

Edith Head says, the building of the right wardrobe for every occasion on your big game hunt for a husband (wife/girlfriend/partner) depends on the man (insert gender pronoun). She said that men readily fall into five categories or types. If you meet someone, and you’ve done your homework (aka asked questions, got curious about their likes/dislikes, lifestyle, work, etc.), then it becomes pretty easy to decide which group your man (or woman) falls into. Then, your job is to dress accordingly. Read the five types below, then identify which type of woman you have your eye on, and proceed with building a wardrobe around attracting that kind of woman. Edith Head says, instead of shopping madly for a lot of new clothes selected without a plan, buy with them in mind.

The Outdoor/Sportsman Type:

This is gonna be pretty clear out the gate. This is the man or woman who you can find at the sports bar, and talks about their favorite sport with little to no encouragement. There are two kinds of sportsmen. The ones who are the spectators, and the ones who are the active sportsmen. The active sportsman are the ones who like to play the sports. Their the ones who talk about their love of tennis, and actually play it. When dressing for this type, think about polos and rugby looks, sneakers, jerseys, baseball hats, things that you would wear to a tennis match, but no need to go out and buy a racket if you have two left feet on the court. Wear the clothes that reflect the style. Old school Abercrombie & Fitch or sportswear. Think Mark Wahlberg.

The Sophisticated Type:

This man or woman is an individual of many interests. They’re aware of everything that’s in. They read the month’s best sellers. They know the head waiter at all the best restaurants, and prides themselves on good taste and being a perfectionist. They’re an articulate and entertaining conversationalist. They’re attracted to someone who is interested in the things that they are. This type has two subtypes. The Super Sophisticate subtype is the one with subdued elegance; so anything overdone, too noisy, or too anything is out. The second subtype is The Good Time Charlie. They’re the eternal one who never wants to grow old. They’re extroverted in every way and wears clothes that look and feel young. Think Will Smith.

The Shy, Conservative Type:

This type has a quiet, un-assumed manner. They’re soft spoken and typically wears solid color neck-ties, has definite opinions, and will never proposition you on the first date. This type looks for conservatism in your wardrobe. They shy away from plunging necklines, baring too much skin, and anything too sexy or sultry in materials like black lace, leather, or hosiery. This person wants to see you looking like a lady or gentleman. Perhaps a little on the plain side. Loud plaids and bold colors shock them, so does loud laughter risqué jokes. They like inconspicuous clothing, introverted in color, design, and pattern. Stick to the classics, and you’ll attract them. Think Idris Elba.

The Far-Out Intellectual Type:

This type is all about avant-garde ideas and art. They delight in wearing exotic, modern prints, exotic color combinations, unusual handmade jewelry, and anything artistic and off-beat. Conservatism is just plain boring to them, so don’t be square. They go for pop art, op art, and modern ballets. Think Johnny Depp, or Kanye West.

The Successful Executive:

This is everyone’s dreamboat. They didn’t get to where they are by goofing off or waiting for things to happen. This is a very definitive person. Someone who knows what they like, what they don’t like, and makes fast decisions. They are impeccably neat, extremely well-organized, and simply cannot handle a sloppy, lazy, disorderly partner. They will expect you to be immaculate always. Your wardrobe should express luxury without ostentation. They respect quality in investments, and in clothing. Think Ryan Gosling.

Follow This Success Formula For Dressing To Get And Keep The Woman Of Your Dreams.

Once you’ve identified which category your dream partner falls into, it’s time to follow Edith Head’s Success Formula For Dressing To Get And Keep A Husband. Again, insert the gender pronoun of choice. The formula works for anyone regardless of gender. Once you have identified your dressing type, simply follow these nine steps to build a selective wardrobe tailored to the type of person you want to date.

  1. Decide what kind of man you want. 

  2. Find out what kind of woman he likes. 

  3. Know what kind of fashions please him. 

  4. Don’t masquerade around in clothes that you hate just to attract a man. Be sure you are really, deep-down his type of woman. If you aren’t, find another man.

  5. Learn all you can about him, his likes, dislikes, hobbies, and interests. 

  6. Be interested in his interests. 

  7. Choose your wardrobe to please him and to suit his way of life. 

  8. After you get him, stay the way you were and don’t relax into a post-marriage slump of careless dressing. 

  9. Look reasonably enticing in the morning, and better at night. 

There you have it, ladies and gentlemen. Edith Head has spoken and given us all clarity on dressing for the type of man/woman you want to date, and possibly marry. This book is a classic. The dress for success formula is timeless, relevant, and invaluable for dressing to get and keep your dream partner.

Try This At Home.

Create a Pinterest board, and name it after your ideal type of man or woman. Example: My Shy, Conservative Woman. Then, pin looks, outfits, lingerie, hairstyles, work looks, etc. of the person you’re attracted to and most want to date. Then, create a second board called My Dating Wardrobe, and pin items to that board of clothing and looks that match the style of the person you want to date. Don’t filter yourself, or judge your desires and preferences, just allow yourself to like what you like. Let it be a creative process. Finalize the boards. Sleep on it. Go back and review it. Then, shop accordingly.

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