1. Hit Men Lace-Up Boot ($130)
The first secret to a good outfit is some sweet shoes.
A nice pair of boots, not the cowboy kind, are the most underrated and eye catching option you can go with. Plus, zippers are great. They work well with pretty much any pair of pants you have, and boost confidence by at least ten points.
Color options: Oxblood or brown. If you can’t go with both, always go oxblood.
2. Under Armour Boot Socks ($11)
Boot socks make those boots wearable all day. They’re pretty great, can double as dress socks if need be, or as some high topped athletic socks if you like that kind of thing.
3. Cole Haan Wingtips ($190)
Seriously. Shoes should be your number one priority. After the boots, a solid pair of wingtips should be up on the grocery list. Besides lasting longer than your car will, these will make you stand out at work, church, and any place you wear them to. A good pair of shoes will have the largest impact on your wardrobe and is pretty easy to incorporate with whatever you have hanging in the closet.
Color options: Oxblood or black. If you can’t go with both, always go oxblood.
4. Funky Socks ($10)
It’s only fair to treat those shoes to a nice pair of socks. Some color and fun in them will open up a new world of style for you. This trend might not last forever, but it’s pretty dang hot right now. Don’t miss your opportunity to liven things up with a pair.
5. Chino Pants ($35)
A classic blend between casual and not-so-casual. Unless you absolutely can’t live life without wearing a pair of blue jeans every single day*, a pair of dark chinos will take you pretty far. These usually can come in slightly more comfy fabrics, too. Nothing wrong with being happy and looking good doing it.
*Those horse people and their ways....
6. Naked & Famous Jeans ($140)
Jeans do have a place in your wardrobe. But probably not like you were taught by your parents. Hate to break it to you, but they didn’t like spending more money on you than they had to.
Move past the limitations they imposed. A pair of dark wash, high quality jeans will change your life. Really, it’s probably time to retire that $30 pair of Levi’s anyways and act like an adult.
7. Saxx “VIBE” Boxers ($30)
Before you scoff at $30 undies, really think it over. Your junk is important. From sitting to standing to walking to sleeping, you probably wear underwear all day long. There’s not another piece of clothing that sees as much action, or has such an impact on your comfort level. Saxx will change your world.
A pouch keeps the jewels nestled all comfy like in a way that is impossible to explain. Ask someone who has a pair of these boxers and you’ll see their eyes glaze over with an appreciative sigh. They won’t be able to explain it either. Just try it out for yourself. You’ll be hooked and thankful beyond all belief. Besides the pouch, these things don’t ride up, they stretch every which way you want to move, and leave you constantly cool and comfortable. Pretty much a work of art in the form of underwear.
8. Leather Belt ($17)
So you have a pair of boots and oxfords. Life is looking pretty good. Sadly, you have to have a belt to go along with those shoes. It’s just one of those things. Nice pants and nice shoes don’t look as sharp without a belt.
Maybe this will change one day, maybe not. For now, you need one. If you aren’t in for just the looks, you can always use that belt as a makeshift weapon in those numerous street fights your manly self keeps getting into. Food for thought.
9. DKNY V-Necks ($33)
If you’re still wearing crew neck (the kind that isn’t a v-neck) t-shirts under your clothes, you should be slapping yourself at this point.
A v-neck looks better when worn by itself and is hidden enough to loosen a button or two under a collared shirt without looking like you have an undershirt on. Get with the times. DKNY has some of the best fitting and comfiest ones out there, within the reasonable price ranges. Don’t waste your money on the other stuff.
10. Oxford Cotton Slim Fit Dress Shirts ($27)
No matter what body type you’re rocking, slim fit is the ticket. The slim fit isn’t about showing off that gym body or anything like that. It’s purely there to make your shirt look like it was tailored to your body. If you want to hide that beer belly, the first step is still a slim fit shirt.
Color purchase order: White, then chambray/blue, follow with a light pink or purple. Solid colors or mini patterns for those. Then, move to a checkered red, maybe a grey, and any pattern that is minimalistic and speaks to you. After these, you really don’t need much else, and will just be cluttering up your closet.
11. Doublju Vest ($90)
Now things are getting fancy. A vest brings a whole new level to your outfit, even though it’s really just a sleeveless shirt with some lining.
Benefits of vests: Slimming, +8 points to style, hides wrinkles and stains, warmth, and makes that tie stay in place.
12. Casual Knit Tie ($12)
Some flair is good. A few may even say it’s necessary.
If you are brave enough to step away from the classic tie, a square ended one will provide a subtle flavor to your outfit. These kind of ties are pretty great. They don’t wrinkle or crease, have more weight and are more comfortable than the usual neck tie.
13. Bow Tie ($10)
Don’t be afraid of the bow tie. Don’t be afraid to tie it yourself, either.
When you know everyone’s going to be dressing it up a bit, you have to bring your game up a bit. A hand tied bow tie is a sure bet for this. You will need some practice tying these, but it’ll be well worth it.
Bonus feature: It’s very hard to beat the loose hanging bow tie look on a dance floor.
14. Plaid Narrow Tie ($10)
Classically stylish. Plaid goes well with nearly any shirt and any jacket as long as they aren’t also plaid.
Be sure to stick with a narrow tie (2″-2.5″). Skinny ties (less than 2″) and the regular (greater than 2.5″) are for children and old men, respectively. The only time it is acceptable to wear either is if you are incredibly small and slim for the skinny tie, or exceptionally tall and broad for the regular.
If you can, try and go for a different fabric than the usual silk. It’ll pop better, and lend you credibility on the style.
15. Sport Coat ($116)
The great stylizer.
At least one tailored sport coat should be sitting in your closet. If you’re feeling hella cheap, your suit jacket can work too, as long as it isn’t black. These beauties are slimming, alluring, comfortable, and concealing. Like shoes, the sport coat is not actually an option though it can be worn less frequently.
A good jacket can make up for a lack of nearly everything else in the clothes department. As long as your shoes look good and your jeans are dark, the rest of your outfit doesn’t matter. If you throw a coat over whichever crappy shirt you have on, you will still look like you know what’s what.
On the reverse hand, a fitted coat worn over a button down shirt will have you signing autographs and taking pictures with strangers who don’t know who you are but want their friends to be jealous of the mysterious celebrity they found at brunch.
16. Pocket Square ($13)
Panache, baby. Up until this point, you’re playing the same game as all the other men who want to look good.
Move past their shortcomings and put one of these in either your vest’s chest pocket or the coat’s.
This is where things really get wild. Any color and any design is acceptable. Go big and bright and fun. A lot of guys are scared that a pocket square won’t look professional enough, or bring some form of negative judgement down on them. Don’t listen to them. They know nothing.
17. Heavy Duty Double Edge Razor ($39)
Truly, the best shaving investment you can make.
There has been an incredible amount of money put into marketing multi-blade razors. Some of them even vibrate. Others have 12 blades and will give you the closest shave of your life. They also all cost a small fortune each year while also coming with a nice dose of razor burn and ingrown hairs.
Instead of falling for the Mad Men advertising, you should look to what makes sense. $40 for the contraption, $14 for over a years worth of razor blades. That’s $54 for the first year of shaving. Then it’s just blades after that. On the other hand, $10 for a multi-blade handle, and nearly $30 for the razor blade cartridges (5, or so). Say you have to buy a new set of blades a month, which is average. That’s $360 a year. Every year.
Oh, and that razor burn and ingrown hair stuff? Ya, it doesn’t happen with single blades such as a safety razor offers. Sure, you won’t get a baby smooth shave. Just a regularly smooth shave, that no one will be able to tell is any different from baby smooth, and your face and neck will be cleaner and more free of pain than a person would ever have thought possible.
18. Skeleton Watch ($150)
A little edge to that style. It’s traditional to have a watch, but a skeleton watch gives the wearer a bit more substance than a cookie cutter Rolex. Plus, those Rolex’s are not cheap, and pretty much no one will get how expensive that boring looking watch is anyways.
Now-a-days, this isn’t necessary to look stylish. But if you want a little extra confidence and a bit more uniqueness in your look, it will definitely help.
19. X-Back Suspenders – Grey ($17)
If you’ve got the right confidence, some suspenders can take the place of that vest and make you standout in a different way. This is an acceptable and attractive trend going on lately.
Wear them with some slacks, a button down shirt, and those sweet boots you now have and no one will question your deep knowledge of looking swell.
20. Eau De Toilette (Cologne) ($46)
A stylish man’s secret weapon.
Polo blue has a very well rounded smell to it, and if you haven’t purchased cologne before, it’s a good one to start with.
The sense of smell affects far more than we credit. A good scent will go a long way with making people perceive you in a better light than you may deserve. Smelling like crap while dressed sharply is a sure way to only impress the people you don’t speak with. Don’t be that guy.
2. Hair Styling Pomade ($12)
The not-so-secret way to make you more awesome.
Along with shoes, styled hair will be a factor that takes a man much further than most give credit. This is more of a subconscious weapon than something overt like a pocket square or fitted jacket.
People may not recognize it, but most will be inclined to trust and like a man who demonstrates he is willing to put effort into his appearance. Fixed up hair is that indicator which few use and even fewer understand. Take the extra 5 minutes, put some pomade such as this in your hair and twist it about till you look competent. True bed head will ruin any attempt at looking good.