Here is an ongoing list of fashion tips & guidelines. While all rules are made to be broken, this is a good start for those having trouble. Please comment and share your ideas! Last updated 19 September 2010
Don't know where to start? Choose shoes first.
Actor Benicio Del Toro once said that he is highly selective about the shoes he wears on film because "they are the root of the character." It's true, conceptually they define your look. But it also makes good sense because most guys have fewer shoe options than anything else. Start with the item that has the least options.
Check the buttons on your shirt and jacket.
If you're committed to wearing a particular shirt or jacket but don't know what other colors to choose: let the buttons guide you. Black buttons mean that black is a good color for your belt, shoes, and/or pants. Brown buttons? Brown shoes. Etcetera.
In most cases, keep materials consistent.
If you're wearing a polyester jacket, try it with polyester slacks. If your pants are made from natural fibers (linen or cotton), wear something similar up top. I would also advise matching fabrics of a similar thickness.
If you do clash styles, keep the color palette simple.
You can pull off a punk-meets-businessman look or a hipster-meets-rapper look if all the colors in the outfit match and/or complement each other.
In most cases, keep the fit similar on top and bottom.
Baggy pants rarely look good with a fitted top. Sometimes baggy tops look good with tight bottoms, but only if the contrast is exaggerated. Fitted shirt + fitted trousers = guaranteed savvy.
The most affordable way to make a statement is with your socks.
When you can't afford a new outfit but still want something to *pop* when you go out this weekend: Buy colorful socks, then roll or cuff your pants. If you have some unique shoes to go with the socks, it will have twice the impact. Now, if you're interested in trying the sock-less look, I recommend "no-show liners" by Calvin Klein. Burlington offers a similar product called "invisible socks".
You don't have to spend lots of money on your wardrobe to look good.
Extravagant spending allows you to spend less time shopping. That's because you can walk into high end stores and pay for their good taste. If your wardrobe budget is limited, you just have to know exactly what you're looking for. When you know the color, style, drape, silhouette and fit of the item you want, you'll find it affordably somewhere or another. Sometimes thrift store finds are preferable to retail finds because they are more unique.
Make a friend who knows how to customize and tailor clothes.
Pay attention to mannequins.
These are often put together by the most savvy people in retail. Out of all the clothes their store offers, these are the ones they like best. You'll also see ways to wear the garments, like the way the pants are cuffed or the way the sleeves are rolled.
Don't be bashful, ask retail employees questions about how to wear things.
They spend a lot of time thinking about these things and (usually) don't mind sharing ideas. Try to find the person with the best savvy-to-friendly ratio, and be specific with your question.
At the dressing room, check out the clothes other people put back.
There's usually a rack at the dressing room entrance, and often you'll see clothes there that you didn't notice on the floor. In many cases these are items picked by savvy shoppers, but which didn't fit properly on their particular bodies.
People say "Only wear what you're comfortable in." Not always true.
Sometimes it takes one awkward first attempt at a style before you warm up to it. Try a new style twice before writing it off.
Always have a clean, fitted white dress shirt.
This is, perhaps, a man's most versatile item. Always good in a pinch, they go with anything, can be worn formally or casually, and look good on all skin tones.
It's better to express yourself than follow the "fashion rules".
A lot of guys are worried about committing a fashion faux pas, so they don't take any chances. But the fashionistas I meet improvise and invent ideas on the spot. If you want to flip up the brim of a hat that wasn't necessarily designed to do that, just try it. If you want to wear a coat inside out because the lining is interesting, just try it. Wear white after Labor Day. Rules exist for the masses, not for individuals.
It might seem obvious, but exercise will make all your clothes fit better.
Iconic fashion designer Rick Owens said, "Working out is modern couture. No outfit is going to make you look or feel as good as having a fit body. Buy less clothing and go to the gym instead."
Steal liberally from movies.
I'm not talking about celebrity paparazzi photos. I'm talking about the wardrobe of movie characters. This accounts for at least half of my inspiration.
Get a magazine subscription.
As magazines transition completely to the internet, print subscription rates have become surprisingly affordable. I endorse GQ, Details, Flaunt, Anthem, Vogue, WAD and Nylon, among others.
Feel really lost after reading this? Copy an outfit from a photo.
Copying a look from a photo can be a great way to start learning about fashion. For example: Let's say you go out looking for the exact suede boot from a photo of Jude Law. Right away you'll start to notice all the different details involved in boots — materials, toe shapes, laces, sole thickness, boot height, etc. Going on a "mission" for an item forces you to assess all of these subtle differentiations. You'll start to get a feel for what's out there, and realize why you like what it is that you like.
—Graham (I) Haynes