What to Wear With Denim

Guest post by Debbie Anderson

Because it's one of the most ubiquitous fabrics out there, you'd think it'd be easy to pair denim with just about anything. And you'd be right. And wrong. True, denim is versatile and mix and match, but to really be your best-dressed self, there's a few rules:

The Rules

1) Don't be a schlub. T-shirts may beg to be worn with jeans, but if the shirt is a wrinkled, faded, dirty disaster, I say skip it.

2) Don't wear the same color denim with the same color denim. If you're wearing a jean jacket with jeans, they should not (EVER) match. This is a neophyte mistake and frankly, not pleasing to women who knew this rule at birth. Also in this vein, denim on denim isn't the best look.

That said, jeans are an enormously flexible wardrobe item and make the man (depending on what you wear with the jeans and to where).

The What and Where

mens jeans black

(ATTACC Straight Jeans. Photo from G-Star.com)

cardigan mens

(Cashmere-tipped Cardigan. Photo from JCrew.com)

Jeans at work: You're going places, and need to look the part. If your office allows casual Fridays or is an informal workplace, it's best to pair a premium pair of dark wash jeans that aren't too baggy (NO SAGGERS!) or too form-fitting. A straight-leg pair looks the most professional and transitions well to drinks after work. Try a hip cardigan on top and a short, sleek ankle boot or oxfords on the bottom. This look tells people that you aren't too buttoned up and know how to have fun while still maintaining respect.

Jeans at night: Try a brightly colored button-down shirt or add some texture with a tweed jacket. Both options say you put some thought into your style and are a man force to be reckoned with – no schlubby t-shirts for you! If you go with this look, oxfords or dressy-casual sneakers (what? it's a thing!) can jazz you up.

mens boots

(Rag and Bone ankle boots. Photo from Barneys.com)

Jeans on the weekends: I like layers. Again, this tells people you spent time getting dressed, but didn't over think your look or try too hard. Give the undershirt-t-shirt-regular shirt look a try. Or add that cardigan or a fitted jacket. If you have to wear a t-shirt, make sure it's fitted and a solid white or non-faded color. Also acceptable? T-shirts that broadcast your favorite charity or interest (music for instance), but aren't six seasons old and armpit-stained. Pair whatever you got with some rugged moto boots.


Experiment with different looks and jean styles. The cool thing is that denim comes in different weights and washes so your options are endless. Just be you, but without the grimy tee.


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