I'm 5'8" and I've spent a lot of time thinking about this. Not in a self-conscious way — just in a practical one. Clothes don't fit right off the rack, so you either accept that or you figure out what actually works. After years of both, here's what I've landed on.
Most advice about dressing taller is either obvious or wrong. "Wear vertical stripes" — sure, technically true, but nobody's building their wardrobe around pinstripes. The real issue is proportion and fit, and once you understand those two things, most of the specific style rules start to make sense on their own.
Fit First, Everything Else Second
This sounds obvious but it's genuinely the thing that matters most. A well-fitting outfit on a shorter guy looks better than a poorly fitting outfit on a tall guy. The reason is that fit creates a clean vertical line — when clothes hang or bunch or pool, the eye reads the breaks in line as shortening the frame.
For shorter men this specifically means: t-shirt hem at the hip bone, not below it. Pants breaking at or slightly above the shoe, not stacking on the ground. Jacket hem at or just below the hip. Sleeves ending at the wrist, not covering the hand. The t-shirt fit guide and the inseam guide go deep on the specific numbers for each.
The problem is that most clothes aren't cut to those proportions for shorter frames. That's the whole reason Abbreviated exists — to solve the fit problem at the source rather than through alterations.
The Vertical Line
After fit, the next most powerful thing is creating a continuous vertical line through your outfit.
Wear the same color family top to bottom. Dark jeans with a dark top, or all-grey, or navy on navy. This is sometimes called a tonal outfit, and the reason it works is that there's no horizontal break at the waist dividing your body into two halves. The eye reads the whole as one vertical line.
Tuck in or half-tuck when the top is longer. A shirt or tee that hangs past the hip creates a horizontal break that cuts your leg length. Tucking — fully or just the front — moves that line up to the waist, which lengthens the leg visually.
Mid-rise or higher-rise pants. Low-rise pants lower the waist visually, which shortens both the torso and the leg. Mid-rise or slightly higher keeps the waist where it should be. This is one reason the Relaxed Straight Jeans work so well for shorter guys — the mid-high rise is doing real work.
What to Avoid (and Why)
Oversized anything. Keep it to one piece at a time: relaxed pants with a fitted top, or a relaxed shirt with slim pants. Not both. The baggy jeans post covers when relaxed bottoms work and what they need on top.
Excessive layering with different lengths. A tee under an open button-down under a jacket creates three hemlines stacking visually. Each adds a horizontal break. If you're layering, keep the pieces close in length or tuck the inner ones.
Cuffing pants when the inseam is already close. Get the right inseam. Abbreviated makes jeans and pants in 25", 26.5", and 28" so you don't have to roll.
The Underrated Moves
Shoes with some visual weight. A very flat-soled shoe can make the leg look like it terminates early. A shoe with a bit of sole height or visual mass grounds the outfit and extends the leg line.
Fitted at the shoulders first. The shoulder seam should sit exactly at the edge of your shoulder on every piece. When it droops, the whole garment reads as too big regardless of everything else. This applies to t-shirts, jackets, and everything in between.
The Short Version
Fit is the foundation. Vertical line is the strategy. Everything else is refinement. Once clothes actually fit your proportions — which for shorter guys mostly means finding brands that build for shorter frames — most of this stuff happens automatically.
If you're starting from scratch building a wardrobe that fits, the wardrobe guide covers where to start, and the jeans guide, t-shirt guide, and pants guide cover the highest-impact individual pieces.