Especially if you’ve only recently started investing energy into looking your best and dressing well, learning how to put together fashionable outfits can be challenging.
From the seemingly vast differences between styles and designers (compare, say, Teleria Zed’s take on trousers to Rick Owens’) to the sometimes minute differences between types of garments (what really differentiates an oxford shirt from a button down anyway?), it’s easy to find yourself lost.
And if you’re feeling lost just looking at the clothing landscape, you’re almost certainly not feeling good and confident, which is what dressing well is really all about.
Fortunately, it really doesn’t have to be complicated or confusing. Once you realize that making any garment look good generally relies on the same three characteristics, you can start to find your place in the world of menswear relatively quickly.
From there, developing a personal style and composing great outfits doesn’t have to be frustration -- on the contrary, it can actually be fun.
From the preppiest of formalwear to your casual everyday garments, understanding these three characteristics will help you compose outstanding outfits every time.
Characteristic Number One: Fit is Always the Most Important Thing
It sometimes feels like I can’t go a single post on this blog without mentioning this, but it’s so true that it bears repeating: fit is everything. It really doesn’t matter how expensive your garment is or what else you’re wearing: if it doesn’t fit, it’s going to look bad on you. Period.
Conversely, ensuring that all the items in your outfit fit properly won’t necessarily ensure that you look amazing, but it will absolutely take you a long way.
When looking to ensure that a garment fits, you should bear in mind that in most cases, simply knowing your size isn’t enough. Size measurements are rarely standardized, and the way a garment fits can vary wildly even within the same brand.
Obviously, a brand’s sizing can give you a good general idea, but instead of only buying Medium shirts, redirect your focus to the garment itself. No matter what you’re looking for, there are almost certainly a few key places you should be looking to ensure that your fit is as good as it possibly can be.
For shirts, for example, it’s primarily the top of your shoulders and the bottom of your sleeves: you’ll know a shirt fits when the shoulder seams align perfectly with the top edge of your shoulders and the sleeves end comfortably at your wrist. For most coats, it’s largely similar. For pants, look to waist size and leg length.
Basically any garment you might be considering to add to your wardrobe will have a similar set of rules for fit, so make sure you’re aware of them when making your next purchase.
If you don’t know them, finding out is easy: if you’re at a store like Blaine’s, for example, any one of our staff members will be able to help you identify a great fit. We also offer in-store tailoring to make any minute adjustments you might need. If you’re shopping on your own, a quick Google search is typically enough to get you started.
Characteristic Number Two: Contrast
Now you’ve added garments to your wardrobe that fit perfectly on their own. Now comes something slightly more difficult, and with fewer hard-and-fast rules: putting together an outfit that looks impressive.
At least in my experience, when men describe having trouble knowing how to put an outfit together, not knowing how to create outfits with an appropriate level of contrast is usually what they mean.
I’ve mentioned this in a recent previous article on this blog, but it applies especially well here: whenever you compose an outfit, you should start by thinking about which one or two of the pieces you’re wearing will function as the “contrast piece”, drawing attention first.
When I started to adopt this strategy, it revolutionized the way I thought about dressing well. No longer was I grabbing items from my closet seemingly at random, hoping that the combination I put together was, at the very least, not horrible. Now I had a clear goal -- emphasize just one or two elements of the outfit -- that I could intentionally strive toward.
In my opinion, picking contrast pieces is one of the most fun parts of menswear as well, and can really help people new to fashion understand why it’s so satisfying.
Instead of treading lightly and hoping not to make a mistake, now the opportunity exists to experiment with colors, patterns, textures, and fit with the specific intention of grabbing attention.
That said, contrast doesn’t necessarily have to be revolutionary: sometimes a little gingham or plaid can be all you need to make an outfit look super satisfying.
Feel free to get as experimental and creative as you personally like when selecting contrast pieces, with a caveat: try to limit it to just one or two items. Too much and you risk throwing off the cohesion of the outfit.
Characteristic Number Three: Cohesion
Though it’s perhaps the most subtle part of any well-composed outfit, it’s also perhaps the most critical: now that you have one or two awesome contrast pieces you’re excited to show off, you need to tie everything together into a gorgeous, completed outfit.
In order to do this successfully, you’ll need to understand how to make an outfit look like it all belongs together. Thankfully, with a little direction, this is pretty simple to pick up.
For the most part, this means that ensuring that the rest of the items in your outfit are understated enough to not draw the eye, but also match the level of formality and color scheme of your outfit.
For example, jeans and lowkey sneakers are a great way to achieve cohesion with a patterned sport shirt, but even neutral-colored suit pants and sandals wouldn’t work. This is why the oft-lamented fedora is such a common fashion faux pas -- not because there’s anything particularly wrong with the hat, but because its all-too-common common appropriation by those wearing otherwise casual clothes is a notorious failure of cohesion.
Once you achieve basic cohesion, you can take things a step further to really amplify the impression your outfit makes.
Let’s say your contrast piece is a jaw-dropping jacket made from the most buttery suede you’ve ever touched. By subtly reincorporating an element from that jacket into the rest of your outfit, you can really underscore how much these pieces belong together: how about some understated suede shoes to really seal the deal? Or referencing the straps on the jacket by swapping normal denim for biker-style jeans?
Making outfits that are cohesive is something that’s easy to start, but really challenging to perfect. Thankfully, now that you have a functional knowledge of how to compose impressive outfits, you can experiment with various ways to reincorporate and reference elements of your fashion until you achieve something totally unique and truly jaw-dropping.
Ultimately, once you understand how to make outfits that fit well and feature good contrast and cohesion, you’ll be well on your way to a wardrobe you can feel excited to wear every day.
Of course, there are some exceptions to these rules -- some high-fashion or super experimental garments, for example, play with typical fit conventions to achieve a distinctive look, and even fully monochromatic looks can look complete and put-together.
But, for the vast majority of outfits, following these rules will enable even complete beginners to put together outfits that feel intentional, look good, and most importantly, are exciting and fun to wear.
Because at the end of the day, the most special thing about menswear is the way it can transform the way you feel in everything you do.
No matter what your tastes might be, every man deserves a closet full of clothes he can feel comfortable and confident wearing to any occasion. By understanding these qualities, no matter what you wear, you’ll be well on your way to understanding what makes fashion so exciting to so many, even if you never come to love it yourself.