Do you ever find yourself stuck wondering if this goes with that?
The missing piece in all this (and what will make your life a whole lot easier) is understanding how casual or formal something is, and then successfully wearing it with other clothes that are similarly casual or formal.
Have you ever asked yourself:
- “Does this
shirt go with that pair of pants?” - “Can I wear these jeans with that
shirt and tie?” - “Is it OK to wear a parka with a suit when it’s cold out?”
When you’re in a tuxedo, it’s obvious you’re dressing formally. If you’re in sweats and a T-shirt, clearly, that’s a casual outfit.
What about everything in the middle?
You have a lot of outfit options between “sweats and a T-shirt” and “tuxedo”, but it’s not always easy putting outfits together, and knowing exactly if this goes with that.
This is where the Spectrum of Style Formality comes into play!
How to use the Spectrum of Style Formality
Within every category—shirts, pants, shoes, outerwear—clothes are listed in order of formality, from least to most formal.
Clothes on either end of the spectrum are more obvious—a T-shirt is clearly informal—it just gets confusing somewhere in the middle.
Now that you have these as a reference, you’ll never wonder how casual or formal something is.
Quick tip: If they’re relatively close in level of formality, they probably go together.
Let’s break it down…
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All Types Of Shirts , From Casual To Formal
T-shirts
Tees (and V-necks) are the base of any man’s wardrobe. They’re also the most casual
Henley
The henley is a more interesting alternative to your basic T-shirt, and can be worn as a layering piece, as well as on its own.
This henley is made from 6.2 oz cotton with a dense, durable knit and a dry feel that will get softer over time.
They come in long and short sleeve versions, and many of them are made from a waffle weave fabric.
Polo shirt
The polo
This polo from Uniqlo features a streamlined, lean silhouette that redefines the shoulders and chest.
Sport shirt / chambray work shirt / OCBD
Sport shirts—everything from your favorite casual
Softer and lighter than denim (thanks to a different weaving process), chambray looks great no matter how you wear it.
An affordable, yet well-made version of the classic Oxford cloth button down in 100% cotton.
I put the OCBD on the spectrum as slightly more formal, because it’s a traditionally preppy (and common American office) style and can be worn with
Dress shirt
Dress
(You should always tuck in your dress
Tuxedo shirt
Only for the most formal of events, the traditional tuxedo
"An elegantly crafted option to elevate your eveningwear, this crisp white tuxedo shirt is cut from soft Egyptian cotton with a pleated bib. Tailored to our slim fit, it features a double cuff, classic collar, and four removable black enamel studs." –SuitSupply
If you’re attending a white tie event—the most formal of formal events—go with a pique bib and wingtip collar. The tuxedo
Spectrum of Style Formality: pants
Shorts
The Flint and Tinder 365 Shorts are cut like chinos, but stretch like a performance short
Perfect for warm days, tropical climates, summer season, hanging out by a body of water, etc.
Joggers
Joggers are usually made from twill or fleece and have elastic at the cuffs and waistband. While the twill version steps up the formality a bit, the silhouette (think sweatpants) is still inherently casual.
A handsome jogger that’s crafted with a style-forward design for endless relaxation.
Denim
There’s a range of formality with jeans. The lighter and / or more distressed your pair is, the less formal it is. The darker-wash, raw, non-distressed versions are considered more formal.
The Levi's 541 Athletic Jeans fit a larger, more athletic build. Crafted with extra room in the seat and thighs and sits at the waist for a more comfortable feel. The tapered leg gives you a modern, sleek silhouette.
Chinos
There’s a range of formality within chinos as well. If your chinos resemble 5-pocket denim, they’re more casual. If they’re modeled after dress trousers both in silhouette and fit, they’re more formal.
Your search for the perfect chinos ends here. Bonobos' chinos offer superior comfort, dozens of colors, and quality that lasts.
Dress trousers
The most formal option of the bunch. Typically made from (though not restricted to) wool, with dressier details like side seam pockets, welt back pockets, tab closure, suspender buttons, and cuffs.
Spier & Mackay makes high-quality and well-fitted modern menswear at a wallet-friendly price.
Spectrum of Style Formality: Casual Shoes
Flip flops (also sandals, or anything that shows your toes)
Flip flops are perfectly fine for hanging out, or when heading to, the pool or beach. Also great for when you’re at the sauna, steam room, or shower at your gym. They don’t belong in any other situation, really.
These are the perfect low-profile beach flip flop sandals for chilling surfside or lounging around (a beach) town or poolside.
Sneakers
Your most casual shoe option. I always recommend a minimalist white sneaker in canvas or leather. Leather elevates your look a bit more (meaning you can dress up white leather sneakers), and they’re also easier to keep clean.
In buttery full-grain calf leather, the Capri Triple White from Koio is the ultimate wardrobe cornerstone.
Boat shoe
Boat shoes aren’t just for preppy New Englanders on yachts these days. Grab a pair in standard tan leather and wear them with denim or chinos for a look that’s a step above sneakers on the formality scale.
Chukka / Driver
A chukka is the perfect transitional weather boot, as well as celebrity chef Anthony Bourdain’s preferred footwear of choice when traveling. It also happens to be comfortable as hell and extremely versatile, working with plenty of different outfits.
"Designed for a tailored fit, an elegant appearance and undeniable comfort, It's the slip-on you'll want to wear everywhere." –Jack Erwin. 10 different colorways available.
The Clarks desert boot—desert boots are a type of chukka—comes with a crepe sole, but other brands make sleeker versions with slim soles that are easier to dress up with trousers and a sport coat.
The driver (or driving moc) is another worthy alternative for your casual shoe collection. These work well in warm weather, my preferred model being made from suede, with a minimal rubber sole.
Casual boots
A rugged casual leather boot sits one step above your desert boots and drivers, as far as formality is concerned, yet still very much on the casual end of boot styles.
A well-made, rugged lace-up boot in a classic silhouette. Available in a variety of colorways and either a slim rubber or chunkier lug outsole.
We’ll get into other, more formal, boot options in the next section.
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Spectrum of Style Formality: Formal Shoes
Dress boots
Dress boots, such as sleek Chelseas (with slim leather soles), Jodhpurs, and other styles are great alternatives to dress shoes, though I wouldn’t replace all my dress shoes with boots.
Well-made, Goodyear-welted, comfortable Chelseas in a variety of leather and suede colors.
While
Because dress boots come in many different styles, it’s difficult pinpointing exactly where they lie on the formality spectrum.
Dress loafers
Loafers are the most casual of dress shoes. There are different versions, from the traditional American beefroll penny loafer, to the moc toe loafer with a longer toe and a sleeker silhouette.
Brogues / Wing tips / Cap toes
There are a wide variety of brogues, from wing tips (brogues with the decorative perforations on an extended toe cap and often throughout the uppers) to more simple cap toes (with broguing only along the edge of the toe cap).
In general, the more broguing, the less formal the shoe is. Get all the details about the different types of dress shoes here.
Plain toe oxford
The plain toe oxford is a very clean, classic option for business wear, a notch above cap toes in formality. Remember, the fewer decorative flourishes on a shoe, the more formal it is.
Made to order. "...the timelessness of the Dean Oxfords will shine through no matter what you pair them with." –Beckett Simonon
Wholecut oxford
Wholecut oxfords have no cap over the toe box, but it may or may not have minimal decorative broguing at the toe. It is cut from one whole piece of leather.
"Crafted from a single piece of rich Italian leather using flexible Bologna construction, this handsome oxford offers elevated appeal." –Nordstrom
Patent leather loafers, oxfords, or opera pumps
These shoes are reserved only for the most formal black and white tie events.
The opera pump is the most elegant shoe to wear with black and white tie, a slipper crafted with a bow in the front and a black satin quilted lining.
Spectrum of Style Formality: Outerwear
Technical outerwear (activity-specific)
Any jackets that are specifically made for certain activities (running, skiing) and / or constructed from a water- and weather-resistant material (windbreakers, rain coat, down coat) would be the most casual outerwear option.
Nike windbreakers are available in many styles and colors.
Vest
Perfect for layering, a vest’s formality can vary. Anything obviously designed for performance, water-, or weather-resistance would be more casual. Quilted vests made from twill or wool in somber colors can be considered more formal (though still, by all means, casual).
Field jacket / Denim jacket
Field jackets (like those modeled after the military-spec M-65) and denim jackets are inherently more casual, though there are ways to combine it with more formal items for that perfect high/low look.
The original jean jacket since 1967. Can buy true to size for the perfect fit, or size up if you want to wear a thicker layer undreneath. 100% Cotton, button closure, hits at hip.
Quilted jacket / Bomber jacket
Quilted jackets, though often made from nylon, can work well with outfits ranging from casual to business casual and provide the warmth and weather protection you may need.
"Pebbled leather and a plaid lining give restrained ruggedness to this classic bomber done in an earthy hue." –Nordstrom
Classic bombers are shorter and hit at the hips, have ribbed cuffs and a ribbed hem, and a front zip closure. Some models have collars, while others don’t. You can find the bomber style made in a variety of materials, from leather and wool to nylon and fleece.
Natural materials in somber colors (leather, wool) would skew more formal, while man-made materials and brighter colors skew more casual.
Pea coat
Pea coats are the most versatile option for a smart or business casual look. They’re warm (especially when lined with an insulating layer) and easily worn with trousers as they are with jeans.
J.Crew updated their take on the famous naval coat with an authentic, straight fit, corduroy-lined pockets, reinforced buttons, and Thinsulate to keep you extra warm.
Some pea coats are made a bit longer, which is perfect if you want to wear a suit jacket or sport coat underneath, but in most cases, an overcoat would work better, simply because most pea coats are too short and you would see the suit jacket peeking out at the bottom hem.
Trench coat / Duffle coat
The trench coat is a dressier alternative to sporty, nylon rain jackets.
They’re traditionally double-breasted and made from 100% khaki gabardine and are longer (to the knee). Trenches also have a few military-inspired details such as epaulettes and a gun flap, as well as features to keep you dry in inclement weather, like sleeve straps, a deep yoke, and storm pockets.
Updated with a soft twill fabric that has a slight sheen and water-repellent coating. Minimalist details give it a stylish look and the raglan sleeves provide a bit more ease of movement.
Bearing the brand's hallmark wooden toggles and jute rope fastenings.This duffle is made from a fine Italian wool blend and finished with a cotton herringbone webbing interior.
While the Burberry trench is iconic (with a price tag to match), you can find a great model from London Fog. Another option would be to snipe a used Burberrys trench coat from eBay.
According to my buddy, Raphael, over at Gentleman’s Gazette, the older Burberrys trenches are better anyway (pre-1999) and were made almost entirely in England.
Just like the trench, there may be many variations of a duffle coat today. The traditional models are longer in the body (anywhere from mid-thigh to knee length), with two distinctive details: 3-4 toggle closures and a hood.
Overcoat / Topcoat
Overcoats—nowadays used interchangeably with the term, topcoats—are coats specifically worn over
Stylistically, they can be single or double breasted, made from heavyweight wool or cashmere in somber-colored wools like grey, black, and navy, to more interesting colors and patterns.
They come with either flap or patch pockets, and notch or peak lapels. Notch lapels are considered less casual than peak lapels, though overall, the coat is appropriate to wear with formalwear.
“Now that I know how formal or casual something is, how do I use it to put together outfits?”
The two ends of the spectrum are a bit more obvious.
- If you’re wearing a casual
shirt and pants, then keep all the other elements of your outfit casual as well. - If you have to wear a tuxedo, keep all the other elements of your outfit formal.
Where it can get tricky is everything in the middle, where clothes range from the dressier side of casual, to the more laid-back side of formal.
Here’s a secret, though: As long as you stick with stuff in the middle of the spectrum, you can’t really go wrong.
Let’s look at an example
- Start with a pair of dark denim, right in the middle of the spectrum.
- Next, a
shirt . Let’s go with a poloshirt . - For shoes, a pair of
chukkas . - And finally, a light jacket. Let’s go with the field jacket.
See how easy that was? You’re basically picking and choosing anything within that middle section of the spectrum.
And don’t forget, you have to imagine the shoe spectrums as one continuous image, from casual to formal.
The
Here’s another example
- Starting with pants, let’s go with chinos this time.
- For the
shirt , an OCBD. - And shoes, we’ll go with work boots.
- For the outerwear, a pea coat (assuming it’s cold out). If it’s not that cold, then a denim or a field jacket.
The lesson here: For the majority of your everyday outfits, just pick and choose from the middle of the formality spectrum.
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“Can I mix the super casual stuff with the clothes in the middle of the spectrum?”
Sure. You can throw shorts into the mix if it’s warm out. Or maybe you want to wear a layering vest with denim and a sport
On the formal end, I would certainly stick to tradition as closely as possible—I’m talking about black tie and white tie—but even with
What other questions do you have?
Now that you know everything in the middle of the formality spectrum is fair game, you should have an easier time putting together outfits, because you know those clothes go well with everything else in the same range.
You can also throw more casual pieces into the mix, and still be in the clear.
Just make sure to respect the tradition of formal wear, should you ever find yourself in the position of going to a black or white tie event.
If you have a combo you’re unsure goes well together, message me on Instagram, and I’ll help you out!