- Stretch Washed Shorts, Grey Bonobos
- Stretch Washed Shorts, Navy Bonobos
- Year’rounder Wool Trousers, Tailored Fit Lands' End
- Wool Dress Trousers Brooks Brothers
- Stretch Chino Todd Snyder
- Stretch Washed Chino Bonobos
- 770 Chino J.Crew
- Alpha Khaki, Athletic Tapered Dockers
- 541 Athletic Fit Levi's
- 512 Slim Taper Levi's
- 502 Regular Taper Levi's
More About Pants
While jeans may be your go-to pair of pants, consider stocking up on chinos as well. You can’t go wrong with a pair in British khaki (a caramel color, slightly darker than your typical khaki chinos) and charcoal.
Same with shorts; the most versatile colors are navy and British khaki. But since you’re wearing shorts in the summer, feel free to grab a pair or two in more adventurous colors.
Finally, one pair of mid-grey wool trousers for those occasions when you need to class it up a bit.
Helpful Pants Articles
- Dress Shirts, Button Down Collar Kamakura Shirts
- Dress Shirts, Spread Collar The Tie Bar
- Oxford Cloth Button Downs J.Crew
- Chambray Sport Shirts J.Crew
- Patterned Sport Shirts Club Monaco
- Plaid Flannel Shirt Todd Snyder
More About Shirts
Stock up on a few T-shirts (or V-necks, if you prefer) which are perfect for casual occasions. I typically stick with grey, white, or black for max versatility, yo.
My sport shirts are a mix of OCBDs and chambrays, plus twills and flannels for the colder months. Depending on fabric weight, most, if not all of your shirts can be worn year-round.
I own a few dress shirts as well, though not as many since I rarely wear suits. My workhorses are my white spread collar and light blue button down collar dress shirts.
Helpful Shirt Articles
More About Midlayers
Midlayers not only add a bit of visual interest to your outfit’s layers, but they help keep you warm. They can replace heavier outerwear during the transitional months, or worn underneath your coat during the colder ones.
I have a number of sweaters, but also love shirt jackets, heavier wool flannel shirts, and quilted vests. These all serve as great midlayers. Stick to neutrals like grey, navy, tan, brown, or black to maximize versatility, but don’t be afraid to throw in a few bolder and more adventurous midlayers into the mix.
Helpful Midlayer Articles
- Peacoat J.Crew
- Topcoat SuitSupply
- Wax Jacket Barbour
- G9 Harrington Baracuta
- Racer Jacket Members Only
More About Outerwear
The number and type of outerwear you buy will depend on how cold it gets where you live. Some guys can get away with light outerwear all year long, while others need to bundle up HARD and would benefit from investing in a warm coat designed to shield you from the elements.
Helpful Outerwear Articles
- White / Neutral Sneakers Greats
- Work Boot Chippewa
- Boat Shoe Sperry
- Desert Boot Clarks
- Loafer Allen Edmonds
- Brogue Wingtip Allen Edmonds
- Park Avenue Allen Edmonds
More About Footwear
Men need 5-6 pairs minimum in their wardrobes. A pair of lace-ups in black and brown, a simple pair of leather sneakers, and a few pairs of casual shoes such as chukkas, work boots, or loafers.
Helpful Footwear Articles
- Second Skin Titanium Trunk Tommy John
- G2 Boxer Brief RibbedTee
- Underwear Packs MeUndies
- Give-N-Go Sport Underwear ExOfficio
- AIRism Undershirt Uniqlo
- Tri-Blend Undershirt RibbedTee
More About Underwear
First off, go with boxer briefs that have a short inseam, between 3-6”. Why boxer briefs? You get the best of both worlds: the support of a brief and the shape of boxers.
I’ve tried plenty of boxer briefs, and my favorites are typically made from a synthetic blend that’s designed with stretch, as well as moisture-wicking and cooling properties in mind.
As far as color, I typically stick with black or grey. Light to mid-grey is great when you have to wear light-colored pants.
Helpful Underwear Articles
Suits and Sportcoats
- Affordable Suits and Sportcoats Spier & Mackay
- Ready-To-Wear Suits and Sportcoats SuitSupply
- MTM Suits and Sportcoats Black Lapel
- MTM Suits and Sportcoats Oliver Wicks
- Custom Suits and Sportcoats Alan David Custom
More About Suits and Sportcoats
The number of suits you need will depend on how often you wear them during the week. If you wear suits every day, you’ll probably want between 7-10 suits for variety (but realistically can get away with 5-6). If you wear them only for special occasions (maybe 1-2x per quarter) then you’ll be fine with 1 or 2.
If you are going for a smart, sharp casual style, you’ll use sportcoats more often. It’s beneficial to have one with a grey base and one with a navy base. I find myself using my glen check (with a brown and tan base) often, as well as a brown herringbone tweed jacket.
Helpful Suit and Sportcoat Articles
- Hair Styling Products (Clay) Layrite
- Hair Styling Products (Pomade) Suavecito
- Hair Care Tame The Beast
- Facial Care Brickell
More About Grooming
I have a simple facial routine. Most nights I use a face wash with scrub, rinse, then follow up with a facial moisturizer. I also have under-eye cream to help with dark circles and wrinkles (that I don’t have, yet, but that I also don’t want).
The ideal hair product is different for every guy. It depends on your hair’s thickness, coarseness, length, and styling preferences. I have thick, straight, medium-length hair, and for me, I found that Layrite’s Cement Clay works well, especially with my side part style.