When you break down clothing into categories, it becomes a lot easier to understand how to dress well. Here are 5 basic categories: shoes, bottoms, shirting, outerwear, and personal accessories... I hope to show some guys a few easy options at all different price points and styles.
*This is not meant to be brand focused, but more on general ideas to incorporate casual classics. I'm not going to talk about suiting or anything like that, most men in this country have a hard enough time not wearing flip-flops to the bar...
Brown Wingtips - wear to the office, easy transition to the bar or a night out, and can also be leveraged as a great casual shoes sans socks and with a pair of cuffed denim or rolled chinos.Work/Hunt Boots - these are what you wear when the weather is shitty or the activity is outdoors or cold.
White canvas sneakers - always classic, from the beach to the streets, you can't beat white sneakers, I'll leave the brand and style up to you.
BottomsDry Denim - these can be worn every single day or after work to dinner... buy quality, wear often, and don't wash... they'll look even better. Yes, if you buy the right dark denim, these are both appropriate for day and night. Buy slim but not skinny, make sure they fit over your boots and get them hemmed to the top of your foot. This will allow you to cuff or roll your denim but keep them from dragging on the ground when you walk.
Chinos - because of the travesty that is "business casual" most people will be able to get away with these at work, even with a corporate business position, and they work well transferring into a casual afternoon around town.
*Trousers - notable exception, if you're down for a dressier option, get some great trousers and wear them as the nicer alternative to chinos. I find lighter colors are always easier to integrate into your existing wardrobe.
I'm going to make this one simple, buy a light blue and white button down oxford for work, under a blazer, and even to a wedding. Pick up a slim fitting chambray for comfortable casual wear that again can be layered under a jacket or dressed up with a tie. Spring and Summer warrant a madras, seersucker, or poplin shirt in light or bright colors and when Fall rolls around pick up a flannel or tattersall print for under your jean jacket with a top coat or parka on top. *I love gingham (little white and colored square pattern) for year around wear, the colors just change.
Trench - this is a great jacket that if made an investment piece can last an adult lifetime... I chose the classic trench coat (and brand) but bought a navy color in a slimmer fitting model for dress and causal.
Parka - parka's are one of my favorites jackets because of their simplicity and comfort, choose a waxed cotton or 60/40 fabric and order a color that you'll wear a lot. The parka is a historically outdoorsy jacket but I wear mine in the city all the time and it always looks great no matter the weather.
Top Coat - Every well-dressed gentleman needs and should wear a top coat in the winter, simple as that. 3/4 length, dark charcoal or navy, front pockets, and an inside wallet pocket for travel or business. This is the only winter dress coat you will ever need, anything else are just options to add in later.
Unstructured (or structured) Blazer or Sport Coat- this is a must, navy in color, and fitted to your body and more specifically tailored to you. Buy something you will wear because you should do just that, wear it a lot. Again another item that can go from meetings to drinks instantly, loose the tie and socks, roll the chinos and you're golden Ponyboy. 2 or 3 button is your call, and for your own knowledge the difference between a "sport coat" and a "blazer" is quite small.
Ties - this is simple, they can be new or vintage, square bottomed or pointed... just buy a medium width and in versatile colors.
Watch - grab a nice military style watch with metal or leather straps, also giving you the ability to switch to a variety of NATO straps. Cheap buy quartz, expensive buy an automatic.
Wallets, bracelets, tie bars, keychains - use discretion and buy what you like to carry and need.. if you wont wear it, save for another investment. Don't listen to anyone on accessories, you don't need 10 bracelets on your arm to be cool, what's cool is wearing what's you.
By picking from the above categories you should be able to build an easy-to-manage wardrobe and have a ton of options while always looking clean and put together. From there you can add in more formal options, maybe look into nicer shoes, and maybe even get a custom suit made.
For reference things you should never do... (these aren't options, and I'm not one to tell people how to dress, but these must be abided by)
- Never for any reason buy or wear square-toed shoes
- Never button the top button on a 3-button jacket, never button the bottom button on a 2-button
- Never allow any of your bottoms to drag on the ground
- Never wear jeans tighter than your girlfriends
- Never shop at Forever 21
If you guys have suggestions or simple additions to share with the audience, please comment below. Try to stick to categories or styles, not brands or fads... Thanks.