10 Must-Have Men's Clothing Items for Better Dating

As we mentioned in our post about How Running Shoes Can Ruin Your Dating Life, getting the right look together can go a long way to making your dating life smoother. Really, it's in your best interest, and for all the future women that you meet, that you go from looking like a Nice Guy, to looking like the hot, cool, hip, sophisticated, edgy...and sexy guy that you really are. To help you get started, here is our list of the 10 "must-have" clothing items for your closet to make sure you look dapper on your next date.

1. Fitted Blazer

We start with the blazer because it is such an easy upgrade to your wardrobe and will make a SUBSTANTIAL difference to your appearance. A blazer elevates your look, mixes with casual clothing items while always looking "dressed up", and even encourages you to stand taller giving you a more confident presence.

The key to the blazer is that it has to be well-fitted. To take things further, look for different textures and patterns that will help you stand out from the all too common grey and navy blazers. The bolder you can go, the more you're going to be perceived as a man of confidence with a carefree attitude. Just be careful to not come off as clownish - most people have an irrational fear of clowns.

2. Pocket Square and Tie

No blazer is complete without a pocket square to finish the look. Suiting accessories like pocket squares, ties, cuff links and tie bars are a great opportunity to play with details and keep things interesting - without going overboard. We have a dashing friend who always wears Italian pocket squares that get regular comments from women. Once he starts talking about the quality of silk and their Italian heritage, he's just a few moves away inviting them back to his place for a movie. 

In addition to the pocket square, having a tie in your closet will come in handy for those more formal occasions when the evening's restaurant is more fine-dining than it is casual. Bonus points with woman-kind if you can rock a bow-tie.

Just be sure to avoid tie/pocket square "sets" and express your creativity by mixing and matching. 

3. White Shirt

A crisp white shirt is a simple staple that you need because it is a common and expected look for most formal occasions. You're not going to express a lot of individuality wearing a white shirt, but you will exhibit a classic manliness. On the other hand, like these gentlemen above, a white shirt combined with a casual outfit adds a simple, but sophisticated look that will get women wondering who you are and why you seem so cool.

Note that some whites are cool and bright, while others are subtly warm. Experiment with different varieties of white to find the white that paints you in the best light. 

4. Patterned Casual Shirt

The problem with solid shirts, even ones with colours other than white or blue, is that they are boring. The kind of things that Nice Guys stick to, not rebels like yourself.

Once you've got yourself that basic white shirt, you should get something with a pattern on it that is fun and expresses your personal style. Like with blazers, the more you can get away with - the more women will notice and flock to you like rock doves to fresh bread.

Patterns range from simple and classic (like plaids, stripes and polka-dots), to prints that can have bold colours or wild images. 

Notice how the simple patterned shirt above makes a suit look more interesting and expresses a lot more attitude and personality than the classic white shirt. Hint: You want to be that guy.

5. Dark Denim Jeans

Jeans are a staple in our modern wardrobes because of their durability. The the key for you is to find a dark-wash denim. The dark-wash keeps the look sharp, and can be easily paired with shirts and blazers for a casual, but elevated evening look. The blessing of jeans is that they are versatile and can be dressed up or down depending on the occasion. 

Finding the best jeans for you can be confusing because there are so many cuts, and different companies give their jeans cute names like Thomas, Clinton, and Gavin. But the main thing you want to remember is NO EXCESS FABRIC. Unless you're looking to pick up skater chicks, you're jeans should not be hanging off your hips and bunching up at your ankles like elephant legs. If your jeans are too long, roll them to create a cuff, which is also a nice way to create a polished look to the bottom of the jeans.

6. Chinos

The alternative to jeans in your closet is the chino.

Chinos (plural) fit right in between casual and formal, and are perfect for those occasions where a jean feels too dressed down, but dress pants feel too much like work. 

Also like jeans, make sure there is ABSOLUTELY NO BAGGINESS. Fitted chinos make you look like a classy guy. Baggy chinos make you look like an IT Nerd who works at Best Buy. Women appreciate a smart guy, but if they are suspicious that you spend more time fixing computers than having drinks with friends, you're dating plans for the near future are going to need to be debugged.

Look out for fun colours and patterns to spice up your closet and help you stand out as the absolutely non-nerd that you are.

7. Casual Shoe

As we mentioned, improper footwear on a date can be as wrong as trying to play soccer in leather-soled, wood-healed dress shoes. You're going to stumble, fall, and generally make a fool of yourself. And you can forget about putting any digits on the scoreboard for the night.

Focus on getting a comfortable, but stylish casual shoe with a heal. Lace ups will be more versatile when you're starting out, but a pair of loafers or driving shoes in the summer can speak volumes about how cool and relaxed you are about life.

To score some extra points with the women, try finding coloured or patterned socks to wear with your shoes. A bit of flair around your ankles will surprise your date - and make her wonder if your undergarments have the same sort of playfulness to them.

8. Casual Seasonal Jacket

For those cool nights in the spring and fall, you need an outer jacket to keep warm. The only question is: Will you look like you're going on a date - or to climb a mountain? 

Keep things cool by going for a leather or denim jacket, or a wool coat that is more appropriate to the city, than for the mountains.

Like with your blazer, make sure you get the fit right. Your jacket should feel snug and look like you're supposed to be wearing it - not something that you are wearing just to keep warm until you can take it off.

9. Knitted Sweater

Layering with sweaters gives you a more polished look, as well as added warmth in the fall and winter seasons.

Simple choices include the V-neck style sweaters which are always available in a rainbow of colours. Try experimenting with faux colours, zip ups, cable knit sweaters, and even turtle-neck sweaters to find a look that you feel great in. Watch out for boxy cuts, and go for sweaters that hug your body, rather than "hang" off your body.

Remember that women are very tactile and having a sweater that looks soft, warm, and cuddly will plant seeds in your date's mind about the perfect way to spend an evening with you as the temperature drops. 

10. Watch

Yes, you do have a clock on your cell phone. But, glancing at a watch on your wrist is way easier, and way classier.

Watches can be expensive, but even when budget is an issue, you can get a decent, fashionable watch for under $200. The watch will be your primary accessory as a man, so don't skimp out on this item, and give yourself the luxury of really finding a watch that works for you.

Avoid watches that look sporty and go for steel link bands or leather bands. 

Watch sizes range considerably, so always try a watch on and ask yourself if it looks "normal" on your wrist. If it's too small, the watch will look like you borrowed it from your kid brother (or son) because you woke up late this morning. If it's too big, it will add a heavy look to your arm, and make your wrist look wimpy by comparison. Remember that women admire strength and character - not wimpiness.

Bonus: Glasses

For those of you who need corrective eye-wear (aka glasses), realize that you are wearing a fashion accessory right on your face, every single day, probably for the rest of your life.

Because they are a major feature of your face, glasses WILL make or break your look. If chosen wisely, they can become a signature look that women will adore. But get your glasses wrong...and you'll look like a big doofus.  

To find a great pair of glasses, first make sure they fit you properly. Your eyes should be approximately centered in the frames horizontally, and slightly above center vertically. Experiment with different shapes and styles to find ones that appeal to you and seem to be natural to your face - not like costume glasses you found in a dress-up trunk.

If you are at all uncertain about glasses, consider going the route of contact lenses, or speak to your optometrist about eye surgery. Whatever it costs, it will be a lot cheaper in the long run than looking like a doofus for the remainder of your adult life.

Wrapping It Up

Don't forget that like dating, clothes are meant to be fun and exciting. Not a hassle filled with rules and restrictions.

It is our belief that if you spend some time developing your own sense of style and understanding what clothes work for you (like many women have been doing since they were little girls), you will actually have MORE FUN going out on dates, and MORE CONFIDENCE. You will be able to express your awesome personality more easily, because your clothes will already be doing some of that work for you. If there's anything that a woman is hoping for when she meets you is that she get's to see the very best version of who you are.

We're confident that with these 10 items in your closet, you will have a good start to your dating wardrobe and know that you've got your clothes handled so you can move on the what's really important: connecting with your date and having a great time.


Kylie & Jonathan want you to discover the power of personal style in your dating life. For help discovering the very best 10 clothing items for you and your dating life, let us know.