I have this exact t-shirt, which I picked up in a Factory store. I love it – you'll feel badass while wearing it with some selvedge jeans and a pair of Red Wings. The faded color and texture makes a noticeable effect on the look, versus a dark, crisp alternative.
A must-have this year, I have a similar olive version that I picked up at Zara on sale. Bombers are great, especially as a layering item if you live in warmer areas. I wear mine with black jeans and white sneakers here in LA as an easy going out look. This will transition easily into the fall. Read our full guide to The Bomber Jacket which details its long history and how to wear it.
The best time to buy anything is at the end of the season it's intended for, and I hate to break it to you but it's basically September. These trunks have everything we like: simple modern style, proper length, and nice touches like the tab button closure. Featured in our swim trunk round up.
I've had these exact shorts for 2-3 seasons and I still love them. Don't be fooled by the ‘oxford' in the title, these are a thin, comfortable material that definitely has a dressier look to them versus what you would expect from ‘oxford'. You can see me wearing them in our ultimate Visual Guide to Shorts infographic and accompanying video below.
I have this shirt, and while it can be worn preppy or dressed up because of the style and pattern, it's subdued colors and large gingham also allows it to wear casual with a pair of jeans and boots. Available in slim and regular fit.
If there was a list of 3 absolutely essential shirts a guy should start with, the small gingham shirt would be in a tight race for #1. But if you're farther along in your sartorial journey, don't let that stop you from picking one up. It's essential because of its sheer versatility. Wear it with a tie and that tweed jacket you just picked up, or easily wear it casually.
Suit jacket ($190) and pants ($109), $299
Need a first or second suit? It'll be tough to find a better balance of price, fit, and quality under $300. This lighter gray color wears well to a wedding, in business settings, or even on a date to a nicer cocktail spot. I wore a suit with a similar fabric in our How a Suit Should Fit guide seen below.
Available in regular, slim, and tall, this moc-neck sweater will carry you well into fall, with a color that pairs easily with jeans, gray dress pants, or chinos of any non-tan color. You can see a similar sweater from J.Crew Factory that I wore in our 1 Sweater, 4 Ways Live Action Getup.
The henley is my favorite chameleon style pick: It's masculine and looks intentional and looks great with jeans or layered under a button up, but when it comes down to it, it's just a t-shirt with buttons. Wear it to the bar to watch the game with your pals and you're already 100% better dressed than the rest of the bros in the bar.
For those who hate pique polos, a comfortable t-shirt like fabric. Even has a pocket!
I've had this shirt in a khaki color for a number of years and it has remained one of my favorite summer shirts. If you're new to linen, it's vital for heat maintenance in the ovens of summer. It's featured in our 5 Crucial Products That Will Keep You Fresh This Summer When It's Hot as Hell.
I'm on my second Magic Wallet, the first lasting me a couple of years, certainly worth this price. I love the way it separates my large bills from smaller ones, and I featured it in my personal Everyday Carry video:
If you could only have two pairs of pants, olive chinos would be second only to dark denim. Plus these are made with stretch for all day comfort. You can easily wear them to work during the day and dress them down for the evening. You can see how to wear them in our Live Action Getup: 1 Pair of Pants, 1 Shirt, 4 Looks that's been pinned on Pinterest over 20,000 times!
This type of mini-pattern shirt has been very popular this year–they make for a smart way to balance dress and casual and are perfect for going out at night. I wore a similar one from Gap in our recent Summer Days Getup shown below, and check out our full post featuring 3 more looks in our Patterned Shirt guide.
Here's another, darker option that's similar to the one Shane wears in our patterned shirt guide.
What's better than dark denim? Denim that stretches with you so you don't feel like a prisoner in your own jeans.
A riff on the classic wayfarer design, but with a thinner profile all around. Easy burners if you're a guy who loses or breaks sunglasses easily.
For the life of me, I've never known why sweatshirts and sweatpants are so expensive, but I sure do love me a pair of slim sweatpants, and this is about as cheap as you'll find them for a pair of decent quality.
With clear stylings from the classic m65 military field jacket, this coat will look great this fall. Wear it layered like the t-shirt and button up below or with a shawl collar cardigan for extra layers.