Levi’s 513 Slim Jeans. These won’t be hipster skinny, but they’re still slim enough to be flattering for a skinnier guy. The color pictured is called Rinsed Neppy and it’s the ideal dark, inky blue your jeans should be. $60 online but I buy my levi’s from TJ Maxx and Marshall’s because you can find them for $25-$30.
Levi’s 505 Straight Jeans. These are the next size up as far as overall circumference goes. They’re still not going to be baggy, but they’re fuller than most. The downside to these is that they’re a more rare cut so you won’t be able to find them through discount retailers. Thankfully, they’re on sale for $48 through the Levi’s site right now (click on the picture to go to the page). The color you want for these is Tumbled Rigid. Having big thighs means that’s the most important area for fit. If these fit there and are too baggy below the knees, you can have a tailor taper them for you.
H&M Cotton Camel Chinos. The camel is more fall/winter appropriate in color but the fact that they’re cotton means you’ll be able to wear them year round. $40
Zara Basic Navy Blazer: The indigo option we were looking at before has been discontinued. However, I think this is going to be a better, more versatile option. It’s still a warm color, but it’s darker hue will make it less memorable – which means you’ll be able to wear it more often without it drawing undue attention to itself. $80
H&M Forest Green Chunky Knit Cardigan: Unlike the V-neck below, this is meant to be worn on it’s own, not as a layering piece. The color with be great with your complexion and the patch pockets and collar make it look a bit more Rugged than dandyish. $70
H&M Grey V-neck Sweater. Another option to wear with both pants and under the jacket or on its own. $13
Gap Red Big Gingham Shirt. You need a large pattern because of your size but gingham doesn’t look as old as plaid does. The red will still be appropriate for fall and winter but the gingham makes it also good for spring and summer. On sale for $42.
Banana Republic Slim Fit White Soft Cotton Button-Up. A white shirt is a staple that’s worth making sure it fits you right. It can be worn with anything. The button-down collar means it has some Americana heritage and doesn’t look too dressy when you wear it with casual clothes. At the same time, you can wear it with your dress clothes and it will still be appropriate. $60
Florsheim Kearney (aff link): Suede bucks are the ideal High/Low shoe for spring and summer. You can wear them with shorts, chinos, or even a casual suit like one made of cotton or linen. The brown suede will work well with everything else you have in your wardrobe as it’s a neutral color. $90
Ted Baker London Soro Espadrilles (aff link): Espadrilles are the adult/traditional alternative to Van’s slip-ons. $70
Dockers Alpha Khakis (aff link): The louder pair is a good way to embrace the casual attitude of spring and summer while the grey pair is a bit more neutral and appropriate after dark. These are the slimmest-fitting, off-the-rack chinos I’ve been able to find and endorse. $120 for both
Polo Slim Fit G.I. Shorts (aff link): The light blue is both casual and neutral and will wear well with everything else. You want slim shorts to keep the proportions between your thighs and your calves more even. $90
JCrew Indian Madras Plaid Shirt: Madras is a type of Indian cotton that wears extremely cool and is ideal for spring and summer. The shape of this and its pattern make it an ideal short-sleeve shirt rather than something that looks like an IT guy’s uniform. $70
JCrew Broken-in Polo. You’ll want more neutral colors like grey, white, or off-white to help balance out the brighter colors in your other shirts and your pants. $45 each
Suit Supply Tobacco Havana Jacket: The pure linen makeup and half lining will make this thing extremely breathable and wearable for summer. The deeper shade of brown and fact that there’s still a half lining instead of no lining will also help this transition into fall very well. The rougher visual texture of linen makes it so this can be worn with jeans, chinos, or slacks. $400
AG Graduate SUD Bone Chinos: Looking through what we’ve already chosen for you in past consultations, I believe you’re ready to venture into the world of light chinos. These aren’t a straight white so they’ll be an easier transition but will still be great for summer. $180
J Crew 9″ Stanton Shorts in British Khaki: This is the safe color, but Mike from D&P likes to wear louder stuff. They have bolder choice if you want to take that step. The 9″ inseam on these means they should hit just above the knee. That’s high enough to prevent you from looking like a skate rat from the 90’s and low enough that no one will think you’re batting for the other team. $65
Rag & Bone Placket Henley: Mike loves henleys and the key to pulling them off well (more like Gosling) is to get something that’s higher quality.. It’s a lighter weight and a more open weave, so it looks a bit more dressed up. $50
Rag & Bone Melange Henley: Same as the one above but without the contrasting placket. The cool green should be very flattering on you as well. $105
Suit Supply Blue Washed Shirt: This is a linen/cotton blend that should really almost be a summer default. It will wrinkle, so just embrace that aspect of it and wear it accordingly. $130
Suit Supply Brown Shirt: This is a brown microstripe that is so fine it will look like a solid unless someone is practically on top of you. It’s similar to the shirt above but will have a little more wrinkle resistance. $100
Converse White Chuck Taylors: These are about as classic and as timeless as it gets when it comes to casual summer shoes. Wear them with shorts and a henley or even with the sport coat. They’re also washable so you can keep them pristine or embrace the dirtiness that comes with white shoes. $45
Nike Roshe: Obviously these are intended as running shoes, but they have a huge following as street wear. I’ve seen Mike in a few photos with red Nikes on and they provide a bit of Rakishness against a normal outfit. I picked up a pair myself a week ago and have enjoyed how comfortable they are and how much of a statement they can make. $75