Just like with white socks there seems to be undue noise about wearing T-shirts with logos. If you wear white socks with a proper pants length no one will care; if you wear a T-shirt with a simple logo and proper fit no one will care.

I find a lot of guys who have the same problem with too-short pants often go for too-baggy t-shirts and shirts. How do you know if a t-shirt fits you properly? If you can fit your fingers SNUGLY into the t-shirt cuff (no more than a finger-ful PINCH) you are OK–anything bigger than this is TOO BAGGY IMO. I see guys walking around in t-shirts that are at least 2 sizes too large (you could fit a large ham in their t-shirt cuffs). For long-sleeved shirts make sure that the sleeves are not too long–a problem for a lot of guys, especially with blazers. Too-long sleeves give the Lurch from Addams Family look aka Dinosaur arms!

I hear a lot of people complain that they find “tight” clothing too constricting and “uncomfortable” which is why they are purposely wearing clothing that is too large. What is unfortunate is that stuff that actually FITS is labelled as “tight”. Have you ever worn gloves that are too large? Didn’t your hands feel lost in them? Don’t you choose gloves that fit you snugly? Clothing fit is the exact same deal.

A wardrobe of solid coloured, simply designed t-shirts are a great way to mix-up your wardrobe. They’re cheap and a rotation of 5-10 of them is a great way to add variety to your wardrobe. Keep fewer staples like blazers and dark jeans onhand. A handful of collared shirts and a bunch of t-shirts gives you an instant wardrobe. They’re less than $10 a piece so there is no reason you should be wearing that XXL Enterprise Online t-shirt instead. If you find yourself reaching for those old favourites it’s time to do a closet purge…as long as it’s in your closet you’re going to wear it out of ‘comfort’.

I’ve covered blazers/jackets/jeans/pant length to death so I’m not going to go into too much more here, other than military jackets are cute and a different jacket per season is good enough (read: 3–winter, spring, fall). And while I think a logo on a t-shirt won’t kill you for beginners who are none too sure about design I’d suggest just sticking with solids and patterns for now or something with a small logo.

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You can do this look with an infinite number of combinations.

All you need is:

-A wardrobe (like 7) of solid coloured easy-care collared button up shirts. PROPER FIT is the most important issue here. Make sure you can button up the shirt comfortably but it’s close to your skin–you shouldn’t be able to pinch more than a fingerfull of excess fabric from your body

-A wardrobe (like 7) of solid coloured / simply patterned no-logo lightweight sweaters. PROPER FIT is also important here but there is more flexibility with sweaters. Just go with solid colours you like.

-DARK RINSE / WASH JEANS…medium to light jeans are very 80’s. PROPER FIT is also crucial here. Make sure they fit your waist and you can’t pinch more than a large fingerfull of fabric from your leg while the jeans are on. LENGTH is also crucial–I don’t believe in all that “don’t wear white socks” nonsense. No one cares about your socks if you are wearing the proper pant length. Proper pant length means your jeans should cover the top half your shoe/foot but are not so long they are dragging on the floor. If they do drag on the floor just get them hemmed.

And yes this means you have to try on clothes in the changeroom!

I would also say you need at least 5 pairs of dark rinse jeans if you don’t like doing laundry.

1 pair of black jeans
2 pairs of khakis
5 pairs of dress pants if you work in an environment with a strict dress code
2 pairs of dress pants (in black, charcoal, navy blue, chocolate brown) if you don’t