Remember those funny ‘mix-and-match' kids' books…
Full of mismatched heads, bodies, and legs?
If your legs don't match the rest of you..
you look like a joke.
You’ve seen photos of models and celebrities rocking ripped skinny jeans with anything and everything. That's supposed to be stylish.
But when you try it, your spouse yells at you to change before walking out of the house. You look like a joke.
Gentlemen, you CAN pair jeans with anything and look truly stylish. The secret is starting with the right jeans.
They're not ripped, they're not skinny… and you don't have to be, either.
Read on to find out more.
This informative article is brought to you by Original Grain, makers of some of my favorite watches. They add a bold touch of style to any outfit — and go great with jeans. Click here to check them out, and use code RMRS for a special discount.
The Most Versatile Jeans
Rule #1 – Keep Them Simple
Avoid flashy decorations, extreme colors and distressed styles. The goal is for jeans to be the canvas, not the subject of the painting.
Dark indigo is the most versatile color, but dark blue, dark grey, and black can work as well. Go for a classic (non-faded) wash — deliberately faded jeans mimic the appearance of worn-out work clothes and are much more casual.
Rule #2 – Nail The Fit
Explore different brands to find well-fitted jeans that work great for your body type. Your jeans should fit closely (no saggy crotches!) but not too closely. Just say no to skinny jeans.
There's nothing wrong with having various fits. Straight leg jeans, which are basically the same size from the thigh to the ankle, are the most versatile. Boot-cut jeans, which are a little flared at the ankle, come second.
Rule # 3 – Know Your Canvas
Jeans are a wardrobe classic. Although jeans in themselves are always casual, the right color, wash, fit, and style can work with just about anything.
Don’t be afraid to spend a little extra — cheap jeans will make your whole outfit look cheap. If money's tight, see what you can find in a thrift shop.
Outfit Building Guidelines
#1 – Balance The Formality
When building outfits, seek balance between the different levels of formality and stack on items accordingly.
For instance, if you're looking to add more formal pieces to your jeans, start with your most formal jeans.
Then add some dress shoes — but make them a more casual pair of dress shoes.
Then find a shirt that looks right with both of them.
If you think about the balance between all the pieces like this, you won't end up looking like a mix-and-match book.
#2 – Balance The Fit
Make sure each item you stack onto your outfit goes with the rest in terms of fit.
The way this usually goes wrong is that your jeans are too baggy and slouchy to look right with a nicely fitted shirt and jacket. However, you can also ruin well-fitted jeans with a sloppy one-size t-shirt.
Outfit Building Order
Step #1 — Shoes
No gym shoes! You might get away with colored canvas sneakers, but the real key to versatile jeans-wearing is the casual leather shoe. Brogues, saddle shoes, suede of all kinds, chukka boots, loafers, monk straps, and Dr. Martens can all work great.
Click here for a fuller guide to pairing dress shoes with jeans.
Step #2 — Shirt
A T-shirt With Jeans
Choose a T-shirt with a close fit (what they call ‘athletic fit') — it should be tight on your chest, and shouldn’t fall past your belt. Pair it with rugged accents like a sturdy-looking belt and leather work shoes or work boots.
A Polo With Jeans
A polo is the slightly classier alternative to a t-shirt, so try it with slightly classier shoes like chukka boots, boat shoes, or loafers. Keep your polo untucked if you're wearing it with jeans alone, but see if it looks better tucked in with a sports jacket.
A Work Shirt With Jeans
Another slight upgrade is a long- or short-sleeved work shirt: one with buttons and a soft, turndown collar. If you want to look a little rugged and rebellious. you can leave this untucked too.
Avoid shirts in a similar blue to your jeans, company logos, and (worse) those rectangular name patches with the cursive script on them.
A Button-Down Or Dress Shirt With Jeans
A chambray button-down is your least formal option here (again, pick a very different shade from your jeans) but you can go as formal as a plain white dress shirt. Light gray or light blue shirts work fine too, as do white shirts with light stripe or check patterns.
Make it look a little more relaxed by unbuttoning and rolling the cuffs (especially important with plain white shirts) — but don't forget to tuck it in. This gives you a chance to show off a nice belt, maybe with a big decorative buckle.
Sturdy leather shoes or boots work best to balance the formality levels downwards, but not too far down.
A Sweater With Jeans
Again, keep it simple. A solid colored sweater in grey, charcoal, off white, tan, brown, dark blue or green is simple to match with almost any color of jeans.
Pair chunky jeans with chunky sweaters, and slim jeans with slim sweaters. (This goes for footwear too.)
Jeans and a plain sweater alone can look boring. You can add interest to the texture of the sweater (e.g. Aran knitting) or the shape of the sweater (e.g. a shawl neck or cardigan), or add accessories or extra layers. A sports jacket works well and can make a bulky sweater look more flattering.
See this in-depth article on pairing a sweater with jeans, including correct layering.
Step #3 (optional) — Jacket
A Sports Jacket With Jeans
No worries about looking too boring here — most sports jackets have either a textured weave, a colored pattern, or both. Pair one with a plain-colored dress shirt and a pair of dark jeans.
For this casual look the jacket can be a little soft and slouchy, but should still fit well enough to define your torso.
Click here for more on sports jackets with jeans.
A Blazer With Jeans
Solid-colored blazers are harder to pull off with jeans, but the right blazer can work.
Go for a slim rather than square cut, and avoid colors that are too close to your jeans (a navy blazer with navy jeans looks like a failed suit.)
Brass buttons can be a bit much. The darker and duller kind that you'd see on a denim jacket are more likely to work than shiny ones. But please steer clear of wearing an actual denim jacket with jeans — aka the ‘Canadian tuxedo'.
See more on pairing a blazer with jeans.
A Suit Jacket With Jeans
Not all suit jackets will work with jeans. Try thrift-shopping to find one that does.
This look is built on deliberate contrast between formal and casual, so remember your balance — don't let your jeans be the one lonely casual piece in the outfit. Try a T-shirt instead of a collared shirt, brightly-colored sneakers, or a colored vinyl belt instead of leather.
Exercise some caution and double-check this outfit in the mirror before you head out.
See more on suit jackets with jeans.
Step #4 — Accessories
#1. A Tie With Jeans
You can pull this off, but you need a more casual tie – and no, that doesn't mean polyester. Instead try:
- Knit ties
- Woven ties
- Skinny ties
- Cotton or wool ties
- Ties with more texture
- Ties with a matt (not shiny) surface
- Fun patterns and colors (not novelty ties, but floral patterns and so on)
Try wearing your shirt collar unbuttoned with a loosened-up tie knot, and consider skipping the tie bar — especially with a knit tie, which may be a bit too thick for it anyway.
Also consider bow ties in the same fabrics. Unless it's black or white, a bow tie is no more formal than a necktie. It's also more suitable for the evening. Neckties start to look a little out of place after 6pm.
DO wear a collared shirt and a jacket — a sport coat is perfect.
#2. Belt Up
There are many casual belt styles that go great with jeans — for versatility in dressing up or down I'd recommend a monochrome braided leather belt.
A trashy rubber watch will ruin these looks as surely as a sloppy graphic tee. You need a watch that looks stylish but not stuffy.
Both metal and leather straps can be worn with jeans. Leather is generally more formal, but a rough, worn-in leather strap is an exception and looks great with a more rugged outfit like jeans and a workshirt.
Or how about wood and metal? This bold, stylish, unexpected combination is the jeans-and-suit-jacket of the watch world. Original Grain offer unique wood and metal watches that will surely get you noticed, for a very reasonable price.
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