I get this scenario a lot: I’m a twenty/thirty-something year old guy. I live in a t-shirt, jeans, and running shoes. I know this doesn’t cut it. I want to look more put together, especially because I like to go on dates, happy hour with friends, and out on the town on weekends. How do I look stylish without sacrificing comfort or my budget?

Look guys, being stylish doesn’t mean spending hours getting ready every morning. Being stylish is about having a wardrobe that’s easy to work with. The key is having staples that look good and fit well.

Here are my top 6 picks to get you started on building your dream wardrobe.

1. Perfect Pair of Black Jeans 

Photo Credit: J.Crew

Black jeans are your best friend. They go with virtually anything and are easy to dress up or down. Look for a pair with stretch (about 1%-2% elastane), so they feel nice and stretchy rather than stiff jeans. Fit wise, opt for a slim fit to keep the look modern. It’s very important to make sure your jeans are the right length, so hem them to the right length. You can ask the sales associate for the best place to get this done. Major department stores usually have an in house tailor. If you lack a well fitted pair of dark blue jeans, get those first.

Some companies that make good stretchy black jeans: Levi’s, Uniqlo, Paige Denim, and AG Jeans. The latter two brands run on the pricier side, but discount stores like Nordstrom Rack are amazing to find a good deal.

2. Henleys 

Photo Credit: Nordstrom

I take it you have plenty of short sleeve t-shirts, but what about long sleeves? Add a couple of buttons at the top and you have a henley! Henleys are a great addition to your wardrobe because they look good and are comfortable. Yes, you read that right, long sleeve t-shirts can be stylish. If you like hitting the gym, henleys are a great way to show off those arms. They pair really well with with jeans and boots to achieve a “smart-casual” look. You can pick these up from stores like Nordstrom, Macy’s, J. Crew, H&M and plenty of others.

3. Boots 

Photo Credit: Nordstrom

Ditch the running shoes and invest in a comfortable pair of boots. One of my favorite day to day style of boot is called a Chukka boot. I love them because they are so easy to wear and can dress up the simplest t-shirt and jeans outfit.

4. Minimal Jacket 

Photo Credit: Superdry

Nothing is worse than having the perfect outfit on and not having anything to wear on top when it’s a little chilly. Having a minimal neutral colored jacket can help complete your looks without sacrificing style. A simple Harrington jacket can do the trick, but feel free to play around with other styles. Here’s a post on jackets and layering to find which ones appeals to you.

5. Button Down Shirt 

Photo Credit: Nordstrom

Alright, this one might be more daring if you’re used to wearing t-shirts all the time, but a well-fitted button down is hands down the easiest way to look effortlessly stylish. They make great outfits for dates, going out to bars or clubs, or just being out and about. If you’re worried about comfort, look for ones with stretch. If you’re not sure about prints and patterns, get a solid colored one to test out. If you want to dive deep into the world of button downs, make sure you check out the Ultimate Guide!

6. Dressy Leather Sneakers

Photo Credit: Zappos

Save the colorful running shoes with a giant logo splashed across the side for the gym and replace your “comfortable shoes” with a fresh pair of leather sneakers. A sleek pair of sneakers can upgrade your style without losing the comfort of your beloved running shoes. The easiest place to start is with a white, grey or black pair. Suede sneakers are also a great option if you like a softer look.

There you have it, 6 easy items you can add to your wardrobe to instantly look more stylish. Besides adding these items to your wardrobe, it’s important to make sure your clothes fit well. Ill-fitted clothing is a style killer! If you’re not sure where to start, check out these guides I made on men’s clothing.

Supreet Chahal

Supreet is a Fashion Stylist from San Francisco, CA. She helps both men and women establish a sense of style and dress with confidence. If you want to work 1:1 with Supreet, visit StyleBySupreet.com. If you're a guy looking to learn more about style, check out PocketStylist.io, a site dedicated to teaching men how to dress well.

Leave a Reply

Close Menu
%d bloggers like this: