Dressing well doesn’t have to be an ordeal.
A lot of it comes down to finding what works for you and sticking to it. This doesn’t mean you should buy a week’s worth of identical outfits, or wear the same jeans until they can stand-up on their own.
Figure out what fits you need, what style you want to portray, and work around those.
Your first priority should be building up your wardrobe so you have some versatile articles for every situation.
1. Classic Denim
Denim jackets will never go out of style. Whether you’re going for for something edgy or a relaxed look like this, a dark denim jacket will see you through most of the year.
With summer coming up, here’s a layered outfit that can hop easily between warm days and chilly nights.
If the jacket is a power accent of the outfit, then that’s a decision that shouldn’t be taken lightly. You can find denim jackets everywhere from thrift stores to Old Navy, but finding a stylish cut is crucial.
Check out Levi’s collection for a variety of fits, but we recommend the Commuter Trucker Jacket.
The other option, since more blue denim is out of the question, is a pair of black jeans.
However, the chinos will give you a brighter, more Summer and Spring friendly look.
Slip on some white sneakers and you’re ready for any warm weather situation.
2. Comfort Casual
Sometimes the situation doesn’t call for any sort of formality.
Maybe you’re meeting a friend for coffee on the Saturday. Maybe you’re going for an easy hike and the weather is on the cooler side.
The rise of athleisure means that the king of comfortable clothing is no longer off limits: Sweatpants.
Sweatpants used to be a touchy subject. For years they’ve been given names like “give-up pants.” But now that high end retailers like J. Crew are making casual sweats, you can feel free to wear them all day.
Check out these slim black ones for a more subtle take. With details closer to chinos, you get all the versatility of joggers with a little bit of subtlety.
Picking out a top can be a challenge. Go too athletic and you’re still limited to the gym. Go with this light pink sweater from Coz for an outfit you COULD workout in, but are probably going to just wear to brunch.
For shoes, we’ve gone with the Cookies and Cream Flyknits from Nike. You need something clean and fresh to pull this off. Your ratty sneakers aren’t going to make the cut.
3. Rough Weather
When the temperature drops and the rain starts falling, you need an outfit that can handle it.
Whether you live in a rainy climate, or you just don’t to sacrifice your style when the storm hits, this is one you can take from the office, to a restaurant, to a date on a Friday night.
The layers start of simple with a white oxford. This slim fit from J. Crew is a basic, well cut addition to your closet.
You can change up the color, but white will give you a bit more of a dressed up feel. Plus, you know white can go with anything.
Over that, you want a coat that gives you protection, but won’t have you burning up. This waxed cotton jacket from Norse Projects will do just that.
If the temperature keeps dropping, just add more layers. This is a wet fall outfit, and layering is the name of the game.
For the shoes, you want something with a little bit of heft to them.
Boots can be a little cumbersome, so go with something like these Clymer 2.0s from Rancourt. They’ll keep you dry without smothering your ankles.
The pants are a basic straight cut from J. Crew. Since they don’t make waterproof pants that won’t make you look like a a crew member on Deadliest Catch, your best bet is to cover everything else.
4. Fashion For Fall
Fall often means bad weather, but when it’s dry, there’s not better time of year to soak up the outdoors.
While this outfit won’t do you any good while you’re apple-picking in the mountains, it’s perfect for hitting the town when the air is crisp and nature is beautiful.
Of course there’s nothing more important to fall fashion than some strong denim.
Check out this pair of selvedge jeans from Momotaro. It’s a slim fit for a modern look.
Pair them with this short sleeve Henley from J. Crew. Henley’s are perfect for adding some rugged appeal.
Add some protection from the elements with this beige number from Baracuta.
The Color gives it an edge of class, especially when matched with these bucks from J. Crew, but the plaid lining screams fall outdoorsman.
5. Hit The Trails
For a look that ready to hit the trails, whether real or imaginary, think dark, neutral colors, thick fabrics, and chunky boots.
While it may be a little too high class for real hiking, this outfit will get you from late fall through winter in style.
It starts with some heavy selvedge denim in a dark indigo, like this pair of jeans from Tanuki.
The fit is a little more relaxed, but still tapered. That will work a little better with these vintage inspired Service Boots from Viberg. You don’t want drain pipe pants over these hefty boots.
Up top, start with this classic fit chambray shirt from J. Crew. It will add a little bit of color and a little bit of class without sacrificing the rugged vibe of the outfit.
Throw an army jacket over top to complete the look. It’ll keep you warm, and really pull the ensemble together. Try the Sapper Jacket from Barbour.
Pull the look together with a stylish backpack from Jansport.
6. New England College
Our final outfit is perfect for a wet autumn in colder climates.
It gives off the impression of a New England Ivy Leaguer that can’t let the rain get in the way of his style.
The monochromatic outer layer is perfect for the muted earth tones of fall, but the light pink peeking out shows that you’re not all gray skies and gloomy weather.
Starting from the inside out, go with a basic slim fit oxford. Any color will do to create contrast, but we prefer pink. This number from Uniqlo is an affordable, yet decent quality option.
Pick it up in different colors to turn this one outfit into several.
For the pants, grab these 60/30 Chinos from Outlier. They added some stretch and water resistance to everyday chinos, so these will cut through the grime of autumn with ease.
Not to mention, 7% elastane means these will probably be the most comfortable pants you own.
Pair them with our favorite bucks from J. Crew to really round off that Cambridge, MA vibe.
Finally, for up top, we’re back to the Sapper Jacket from Barbour. It’ll keep you warm and dry regardless of what nature throws your way.