1. New Pompadour
It’s a modern take on the classic Pompadour (make this a link to a classic pompadour pic) but there’s still going to be that signature volume on top. I find this hairstyle very sexy, especially when the hair’s finger-combed back so that it looks a little “piecey” and not so perfect – every woman will want to run her hands through your hair.
Characteristics of the New Pompadour
- When the cut is tight and tapered on the sides, but longer and textured on the top.
- The top will be either swept back, like the James Dean picture below OR back and to the side, like the Justin Timberlake picture. You’ll maintain this direction and high volume on top with a blow dryer and some wax or pomade.
2. Freeman’s Cut (Undercut)
When I see this hairstyle on a man, I instantly think he must be a badass and could give two shits. This haircut isn’t for someone who wants to blend in, so it’s actually a really easy way to fake being cool, or add a dimension of personality that women will be attracted to.
Characteristics of the Freeman
- When the hair is cut really short (using a 1 or 2 on your clippers) or shaved on the sides and back of your head, but left about 2-4 inches longer on top.
- The top of your hair is going to be swept straight back. The styling is really quick and easy.
3. The Crew Cut
This haircut is also known as the “Ivy League Cut.” It always looks great and is super low maintenance, so it’s a favorite of a lot of men, and I don’t blame them.
Characteristics of a Crew Cut
- Tight on the sides with a natural fade of the sideburns and back of the head. The top will be a little bit longer and even length across the whole top of the head.
- In terms of styling, there’s really not much to do except brushing the top front area up.
4. The Quiff
- There’s lots of different variations of the quiff, from short to longer versions, and a cleaner, more controlled styling to a messier, tousled look. This is another haircut that makes me want to run my hands through your hair. I love when it’s styled a little messy because it looks really sexy, masculine and cool.
Characteristics of the Quiff
- When the top of your hair is on the longer side and the sides and back can vary in length but it should always be kept shorter than the top so there’s a definitive contrast.
- This kind of haircut will work perfectly on men who have naturally curly or wavy hair.
- To achieve the volume on top you’ll want to blow dry the top of your hair and then add some styling product to push the hair back and to the side.
5. Classic Businessman
Also known as the Don Draper haircut from Mad Men, it’s a classic taper haircut with a side part hairstyle. I love this timeless and formal hairstyle which looks great in all settings.
Characteristics of the Businessman
- The top is left up to 2 inches long and the sides and back are tapered with scissors or hair clippers.
- To get the hairstyle, take your hair product of choice and run it through your hair while it’s still damp. Take your comb and create your side part. Then create a small wave on the front of your hair by combing your bangs up and back towards either side. Comb back the sides of your hair.
- If you want a little messier than use your fingers as a comb when pushing the top of your hair to the back towards the either side.
- If you want a wet finish, use a pomade with a bit of shine to it.
Stop saying ‘Maybe’
Whenever you’re making appointments, don’t say, “Do you maybe want to grab drinks or dinner?” Instead, take charge and be more direct – “Let’s grab drinks!”
Witty and Sarcastic Humor
Even if the humor is a little mean-spirited, but not directed towards us, we’ll find you more attractive due to your sharp wit.
Roll up your sleeves
If you’re wearing a long-sleeved shirt, I’m talking about literally rolling up your sleeves in front of us. Our eyes will instantly go to your forearm which we find very sexy.
Good w/ kids & elderly
Women are always going to find this attractive because it’s show us what kind of partner and family man you’ll be in the future.
Not always available
It’s good to be available, but just don’t be so available. We respect a man who has a busy schedule and isn’t always free to hang out at the drop of the hat.
Not ashamed of hobbies
Women find it very endearing when a man gets really excited about a quirky hobby or similar things that you wouldn’t have guessed by looking at him. Just don’t go over the line with something creepy like, My Little Pony.
1. Why are you so serious?
Other similar winners: Why aren’t you smiling? or the other gem: C’mon, girl – smile for me.
Because I’m not smiling means that I’m serious?
2. You look different.
If you’d like to know what’s different, ask us something specific like, “Did you get a haircut?”. We’ll probably say no and then tell you what it is, if anything. At least then it doesn’t sound so bad.
3. Is something wrong?
Or similar questions like: Is everything okay?; Did I do something wrong?
Something is about to be wrong if you ask me that again.
4. Why are you wearing that?
5. Why won’t you talk to me?
Or the equally stupid follow-up: Am I not good enough for you?
By asking this question, you effectively just made me not want to talk to you and definitely showed yourself to not be good enough for me.
6. Are you having fun?
AKA: You don’t look like you’re having a good time; Why are you so quiet?
This question just killed any fun I was having. Thanks!
7. You look stressed.
Alternates: You look tired; You look upset.
These stupid statements are stressing me out – that’s all!
8. Why’s a girl like you still single?
Or the ever-popular: Where’s your boyfriend, he doesn’t like showing you off?
Just buck up and ask if I’m single – I’ll tell you.
Dark Wash Jeans
White Dress Shirt
Lace-up Dress Shoes
Casual Lace-up Boots
- Boots and Shoes
- Coats & Jackets
- Shirts & Sweaters
- And various Accessories
Like always, I only recommend products that I’ve personally touched and worked with – in all budget ranges. I’m fortunate in that I get to touch hundreds of menswear items a week, so when I say something is great, it’s not because I got paid to sell you a bunch of cheap [email protected]*t like everyone else – it’s because I have actual experience with these items.
This series is a supplement to my Men’s Wardrobe Essentials Series. In that series, I covered the year-round essentials that you should have in your closet already. If you haven’t read/watched those articles and videos, do that first so we’re on the same page.
The Best Colors & Patterns For The Season
Since I don’t want to go over colors and matching them in every single video in this series, let’s talk about Fall and Winter colors and patterns and how to match them to your outfit and skin tone.
The appropriate colors for this time of year are:
- Mid to darker greens
- Shades of browns (camel to dark brown)
- Shades of blues (light chambray to navy)
- Shades of gray (light, medium and dark)
- Burgundy and wine colors
- Darker or “burnt” Orange
As for patterns, this is what I like to call “plaid season”. It’s the best time of year to wear plaid because its more visually heavy and pairs nicely with the heavier clothing you’ll be wearing, like sweaters, wool coats and wool trousers. For outerwear and Fall/Winter suiting, I love a good windowpane, as well.
HOW TO Match & wear COLORS BASED ON YOUR SKIN TONE
If you’re darker skinned, this is less of an issue because those colors look great on you. But if you’re pale or yellow-toned, this can be a disaster if you don’t know what you’re doing.
PALE or Yellow Skin
If you’re pale or yellow skin toned, make sure that your camel, burgundy, or burnt orange pieces are an outer layer and not a base layer. Let me show you what I mean.
You’ll notice in the below photo that I have my pale model wearing a camel sweater. But you’ll also hopefully notice that there is a white ring of a t-shirt sticking out from under the collar.
This is VERY important because that little sliver of white provides separation between the skin and sweater. The camel color would completely wash out his skin tone and make him look sickly if it wasn’t there. It’s much more apparent in person than images, too.
Below is the same model wearing a burnt orange sweater, but you’ll notice that I have a gray plaid shirt under the sweater to provide that necessary separation of the sweater from his skin. If that wasn’t there, the orange would bring out the pink tones in his skin – which would make him look red and flushed.
And lastly, going back to my white sneaker article/video, I styled my model in a burgundy bomber jacket with a black t-shirt. The shirt provides the necessary visual separation to not bring out the pink tones in his skin.
If I had him in a black jacket and burgundy t-shirt, instead, he would look oddly red-faced. This combination, though, would look awesome on someone with darker skin.
So to recap: If you have a pale or yellow skin tone and want to mix Fall/Winter colors into your wardrobe, just make sure it’s an outerwear piece with visible neutrals (white, grey, black, navy) underneath.
Now, if you’re darker skinned, you can still follow the pale/yellow skin rules above because it’s the classic way to wear color and looks good on everyone. So when in doubt, wear your statement color as outer layers. But with darker skin tones, you have the added advantage of being able to wear all these colors in your shirts and sweaters and then have neutral outer colors because the contrast looks great with your skin tone.
Here’s some examples of outfits that look great on darker/warmer skin tones that would look horrible on a guy with yellow or pale skin:
Just do me a favor, though. Don’t go overboard with color. Have one standout color in your outfit and then pair it with neutrals everywhere else. When you start throwing burgundys, greens, blues and browns all in one outfit, it’s just too much going on.
How To Wear PLAIDS AND PATTERNS
It’s a great time of year to incorporate them into your wardrobe. I prefer to keep the plaids to collared shirts because it looks good on everybody and is really hard to mess up. You can wear them on their own, with the sleeves rolled up, or throw on a nice solid colored sport coat, bomber or trucker jacket over it and the shirt will look great.
The key to wearing patterns is to make sure the rest of the items in your outfit – pants or jacket/sweater/coat are solid neutral colors. It’s when you start mixing patterns that’ll get you in trouble real quick.
So pick an item in your outfit (normally a shirt, sweater, jacket or coat) for a pattern and then have everything else be a solid color. And also make sure that just like with your ties and pocket squares, you want a color in your plaid to be a similar shade of one of the colors in your pants or jacket/sweater. Then you’ll have a nice, classy and cohesive look.
My Favorite COLOR COMBINATIONS For The Season
Here’s some color combinations I love and use with my clients during this time of year:
- Green and blue
- Gray and brown
- Blue and brown
- Burgundy and blue
- Burnt orange and blue
These are my go-to colors and if you stick to these combinations, you’ll look sharp and timeless during this season.
So without further adieu, let’s get into the Men’s Fall and Winter Essentials.
So here it is: These are the quintessential shoes that every man should have in his closet for year-round wear. Anything outside of these are specialty items, like snow boots, so they’re not included in this article.
Have questions? Curious what others think?
Join us in the comments section of the video above.
1. Athletic/Running Shoes
Buy the Nike Roshe FlyKnit in gray
There’s nothing better than a sleek pair of athletic shoes. Not only can they function as your gym shoes, but they can be worn with your casual outfits, as well.
I recommend sticking with a black/white, black/grey/white (like above), or navy/white color to ensure that your sneakers compliment all your outfits. Other crazy colors like neon green or a bright red will only draw attention away from your outfit which is why I’m not recommending those colors. You probably wouldn’t know it, but these shoes are one of my clients and almost a year old.
Since all of the shoes I’m recommending have white soles, I highly recommend Jason Markk’s Essential Shoe Cleaner Kit. Just give the soles a quick scrub with the included brush and soap every few weeks and they’ll look good-as-new for a long time.
2. White Sneakers
Buy the Adidas Stan Smith Sneakers
The second pair of shoes you should own, is what I’d consider an absolute essential to any well-dressed man’s wardrobe, which is why they were also included in my Men’s Wardrobe Essentials series.
They’re clean, classy and look great with a lot of your casual, even up to a little more dressy, outfits. Throw on a nice fitted blazer and some dark wash jeans with them and they’ll look amazing. See here for outfit inspiration images.
Under no circumstance should you wear these with a suit, though. That’s a trend that’s been floating around for a few years and I just think you’re not doing a suit justice by dumbing it down with sneakers.
A quick note, because it’s been brought up in the comments of my White Sneaker Video – Jordan’s and Air Force Ones are not the same as these – even if they’re white – because the shape and profile of those shoes are completely different. Notice how sleek and simple the profile of the above shoe is – THAT’S what makes all the difference. Jordan’s and Air Force Ones are chunky looking and have a very specific look that a lot of men can’t pull off.
3. Suede Driving Moccasins
The third pair of shoes you should own are suede driving moccasins. I’ve already covered these in my Summer Essentials Ebook, but they’re also great shoes during the other parts of the year, depending on your climate.
If you’ve never worn a pair, then you really should try them because they’re the most comfortable middle ground between a dress shoe and a sneaker and after they’ve been broken in a little bit, they’ll feel like you’re wearing a pair of socks.
I have these ones here by Tod’s that I really love. Stick with dark brown first, then you can add a tan color and then navy which will cover you for any outfit you can wear outside of a suit – which you should never wear driving mocs with. The construction is fantastic and they hug your feet nicely –
which is important because a lot of cheaply made driving mocs tend to look loose around your feet which is to be avoided.
There’s three things to remember about driving moccasins:
Only wear no-show socks with them. I did a whole video about socks so check out the link in the video description.
Before you wear them for the first time, make sure you Scotchguard them in order to protect the suede from dirt & liquids as much as possible.
They’re going to get dirty, it’s inevitable with suede. So buy them knowing they’re going to have a shorter shelf life than the rest of your shoes, but trust me, you won’t care because they’re so damn comfortable.
4. Oxford Or Derby Dress Shoes
The fourth pair of shoes you should own are Oxford or Derby dress shoe with a sleek profile and round toe. I’ve covered these extensively before, but every man needs at least a black and possibly brown pair of dress shoes in his wardrobe. They go well with all outfits outside of a super casual outfit (think: t-shirt and jeans). And since you should at least own one suit, these are necessary because you can’t get away with wearing any other shoes with your suit. Remember: the goal is to have you looking amazing, no matter the scenario or outfit.
I prefer plain toe, but you can also get cap toes, but I will grab a pair of plain toed Oxfords or Derbys over any other kind of dress shoe 99% of the time.
As for brogueing, burnished toes, oxblood or other unique colors, don’t get me wrong, I love them, but that’s like two levels down the road if you’re new to dressing better. They’re very specific and won’t go with a lot of your outfits, so grab them after you’ve invested in a classic black and dark brown oxford.
5. Brown Leather Boots
The final pair of shoes – in this case – boots you should own are a pair of brown leather boots.
They’re utilitarian in that you can wear them in a lot of adverse weather situations as well as in more elevated casual outfits. I prefer brown because boots are usually more geared toward the cooler months, and brown is a great fall/winter color and it goes AMAZINGLY well with the dark wash jeans and wool trousers you should already own. But don’t be mistaken, you can also wear these year-round.
It’s been asked this a few times by viewers, so unless you’re going for the lumberjack or American/Japanese worker-style look, don’t wear these boots with a suit because these ARE NOT DRESS BOOTS.
I love the pebbled brown leather and goodyear welting of the Purdey boots above, which is why they’re my top choice. Trust me, I spent a lot of time finding the best boots out there and these are hands down my favorite.
If you want to know how to tie your boots properly like this so don’t have a bunch of excess laces flopping around, check out my video about how to properly tie men’s shoelaces.
O’Keefe Algy Split-Toe Weatherproof Pebble-Grain Leather Boots
Crockett & Jones Islay Wingtip Boot
Frye Jones Lace Up Boots