Hooded sweatshirts (“hoodies”) are one of the toughest pieces to wear in a stylish way. If you aren’t careful, you’ll end up looking like a thuggish kid who’s been held back in high school for a few extra years, or like an old slob who doesn’t put any thought into what he wears. It’s a shame because hoodies are super comfortable and easy to throw on at a moment’s notice.
Because they’re so hard to pull off, I only own two hoodies myself: a simple grey zip-up hoodie and a plain maroon hoodie with a criss-cross collar. I may add another one or two to my wardrobe this season. Here are my three personal rules when shopping for hoodies:
- Proper fit is the most important thing. The biggest mistake you can make when wearing a hoodie—like most articles of clothing—is to wear one that’s too big for you. The hoodie’s shoulder seam should rest on top of the end of your clavicle (follow your collarbone all the way to your shoulder, and that’s where the seam should be).
- Simpler hoodies are easier to pull off. Colors should be mostly limited to one, with a secondary highlight color being acceptable on a case-by-case basis. Solid is best. Avoid loud patterns like plaid and checks. Big logos and printed graphics are juvenile, while singular small logos can be OK. However, it’s best to have zero images.
- Avoid front pouch pockets. Yes, they’re comfortable. Yes, it’s nice to have a place where you can store stuff. Unfortunately, pouch pockets bring down the look of most hoodies, and they encourage poor habits (like hiding your hands when you feel uncomfortable). It’s too bad that most hoodies do have pouch pockets, so sometimes you can’t do anything about it and have to suck it up.
Here are some of my favorite hoodies that I think are quite stylish, starting with the simplest and most conservative in design (safe) to ones that are a bit more daring and unusual (risky). Whatever you do, make sure it fits right and wear it with confidence.
Here we have the most basic hooded sweatshirt you could possibly find—and that’s OK because it can be stylish all the same. The model in the photo is wearing it one size too big. Imagine how much better it would look if it actually fit properly! The solid color and the lack of a pouch pocket make it extremely versatile, and you can dress it up with chinos and boots or dress it down with jeans and sneakers. Uniqlo is one of the most affordable clothing brands for men, so it won’t even hurt your bank balance.
You don’t have to be athletic to wear this hoodie by Under Armour, although it will definitely fit better on an athletic frame. The pouch pocket is sleek enough that it doesn’t detract much from the overall aesthetic and the heather pattern is both simple yet visually interesting. I don’t like the logo on the chest, but it’s small enough to not be a deal-breaker.
Carhartt is an American workwear brand that specializes in outerwear. You may have to size down to make sure this hoodie fits you, but it’ll look great when you get it just right. The pouch pocket isn’t so bad when split by the full-through zipper and it’s made of hearty material so it’s practical in addition to stylish. That logo placement is unfortunate, but it’s only a small negative mark on an otherwise nice hoodie.
This hoodie by J.Crew is insanely comfortable. What else would you expect from French terry cloth? Plus, it looks great. Again, the model in this photo is wearing it a size too big so make sure you size it correctly for your build. I love the subtle criss-cross at the collar, but otherwise it’s a simple design with a downplayed pouch pocket. This one will definitely get you compliments when worn!
Not much to say about this one that hasn’t already been said above. It’s simple, downplayed, but just interesting enough with the marled pattern. It should fit a little snugger than how this model is wearing it.
The contrast between the solid navy and the white highlights make this hoodie by Superdry a visual treat. The only real downside to this one is that you can’t wear it with dark jeans, otherwise your entire outfit will be one unsightly shade. But worn with grey fitted sweatpants or faded jeans or light-colored shorts or even beige chinos? Yeah, it’ll look nice.
I really love this hoodie design. The base color is a lovely shade of navy, and the pattern across the shoulders is both tasteful and similar enough in tone to the base color that it doesn’t stand out in a jarring way. The zip-through is clean and appealing, and the pockets don’t have the pouch design that hoodies normally have. They’re just regular pockets! Overall, it’s a pleasing look that’s sure to draw compliments when you wear it.
I generally try to avoid logos on clothing, but when the logos are used for aesthetic effect, it can be all right. In this case, there are a few things going in favor of the hoodie’s style: the color contrast between black Adidas logos on that particular shade of grey is pleasing, the logo size is just big enough to be interesting but not distracting, and the logo pattern is unpredictable but not provocative. Obviously it should only be worn casually, but it is a stylish option for such circumstances.
Camouflage can be hideous when worn incorrectly, and just because a hoodie like this has the potential to look nice doesn’t mean it will always look nice when worn. I probably wouldn’t wear it, to be honest, but that’s only because it’s too street-style for my personal tastes. However, matched with other pieces of simple, well-fitted, earth-colored attire—like dark brown chinos, dark navy jeans, deep chestnut boots—it could be a real winner.
This is about as adventurous as I’d ever be with a hooded sweatshirt. It’s certainly not to everyone’s taste, and whether I’d actually wear it would depend on how it looked on me after trying it out in person, but no doubt it’d look great on the right person in the right outfit. The reason why the bottom half works is because the rest of the hoodie is kept minimal: no patterns, one solid color, no pouch pocket, and the experimental aspect of the design is isolated to one region. If you’re going to wear this, rock it with confidence!
