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I spent about 15 hours over a couple of weekends putting together a visual outfit library. It's a bit embarrassing to admit, but I got really into it. I'm posting it here because the format might be useful.

I'm 33, work in tech, and almost never need to dress formally. Two years ago, I wore the same black T-shirt and jeans everywhere. Then a friend dragged me to Massimo Dutti, and I bought a suede jacket on impulse. That was the gateway drug. I started reading Permanent Style, lurking on r/malefashionadvice, and watching far too many YouTube videos. Now I make spreadsheets about trousers.

I like the semi-casual end of the spectrum, polished enough to look intentional, relaxed enough that I don't seem overdressed at a coffee shop. I don't own a suit, and I probably should, but that's a problem for later.

One change made the biggest difference: I stopped thinking about shirts first and started with trousers. Pick the trousers, decide how formal you want to look, then match a top and shoes. It sounds obvious, but it got rid of about 80% of that \"I have nothing to wear\" feeling. That's why everything below is organized by trouser type.

I haven't included underwear, socks, or gym clothes. For all of that, I stick to boring Uniqlo basics. I don't care how I look while deadlifting.

Straight dark blue jeans

Most versatile pant I own. Go with basically everything.

\"White — **White Tee + White Sneakers.** White crewneck tee, white leather sneakers, silver watch.

\"Navy — **Navy Blazer + Brown Boots.** Navy blazer, white or light blue OCBD, brown leather chelsea boots.

\"Grey — **Grey Crewneck + Loafers.** Grey crewneck sweater, brown suede loafers.

\"Charcoal — **Charcoal Overcoat + Merino Crewneck.** Charcoal wool overcoat, mid-grey merino crewneck, white oxford collar, dark brown chelsea boots.

\"Brown — **Brown Suede Trucker + Charcoal Rollneck.** Dark brown suede trucker jacket over a charcoal rollneck with dark brown boots.

\"Black — **Black Leather Jacket + Black Boots.** Black leather jacket, black t-shirt, black boots.

\"Camel — **Camel Overcoat + Chelsea Boots.** Camel wool overcoat, white OCBD, brown chelsea boots.

\"Olive — **Olive Field Jacket + White Tee.** Olive field jacket over white tee, white leather sneakers.

\"Rust — **Rust Crewneck + Brown Chelsea Boots.** Rust crewneck sweater, white oxford underneath, brown chelsea boots.

\"Burgundy — **Burgundy Sweater + Brown Boots.** Burgundy crewneck sweater, brown leather boots.

\"Pink — **Pink Oxford + White Sneakers.** Light pink oxford with rolled sleeves and white leather sneakers.

Baggy dark blue jeans

\"Fitted — **Fitted Black Tee + Chunky Sneakers.** Fitted black tee tucked or half-tucked, chunky white sneakers, belt visible.

\"Oversized — **Oversized Hoodie + High Tops.** Grey oversized hoodie and white high-top sneakers.

\"Shearling — **Shearling Bomber + Black Knit.** Dark brown shearling bomber over a black knit sweater with black leather boots.

\"Canvas — **Canvas Chore Coat + Work Boots.** Tan canvas chore coat, white heavyweight tee, and brown work boots.

You need a fitted or structured top or the whole thing looks like you borrowed someone else's clothes. High rise helps. I've been rolling the hem to break up the volume. The winter version only really works when the puffer, liner, hoodie, or bomber is intentional and the boots are chunky enough to carry the weight.

Straight light blue wash jeans

\"Denim — **Denim Jacket + Brown Boots.** Dark denim trucker, white pocket tee, and brown boots.

\"Cream — **Cream Cable Knit + Tan Boots.**

Light wash reads way more casual than dark, so you need a darker or more saturated top or the outfit has no anchor. Denim-on-denim (denim jacket + light jeans) works but only if the shades are actually different. Someone on MFA told me \"at least two shades apart\" and that seems right.

Baggy light blue wash jeans

\"Striped — **Striped Tee + Canvas Sneakers.** Navy-white striped tee with white canvas sneakers.

\"Dark — **Dark Denim Jacket + White Tee.**

\"Graphic — **Graphic Tee + Skate Shoes.** Oversized graphic tee and skate shoes.

\"Varsity — **Varsity Jacket + Grey Hoodie.** Navy varsity jacket over a grey hoodie with retro white sneakers.

Straight black jeans

\"Taupe — **Taupe Cardigan + Black Chelsea Boots.** Taupe shawl-collar cardigan over a black mock-neck knit.

\"Forest — **Forest Overshirt + Black Boots.** Dark forest wool overshirt over a black mock-neck knit with black leather boots.

Black jeans read dressier than blue. They fade fast though — I ruined my first pair tossing them in a normal wash.

Baggy black jeans

\"Flannel — **Flannel Shirt + Black Boots.** Red-black flannel open over a white tee.

\"Quilted — **Quilted Liner + Black Hoodie.** Olive quilted liner jacket over a black hoodie with black combat boots.

All-black only works if you mix textures. Chunky knit over a smooth tee, matte boots against coated denim. Without that it's just a dark blob. And if the jeans are baggy, the top needs to be intentional or it reads pajamas. Shearling, quilted liners, cropped puffers, brushed flannel, heavy hoodies — that's the lane. Sleek minimal layering looks weird with these.

Straight khaki chinos

\"Emerald — **Emerald Tee + Tan Boots.**

\"Waxed — **Waxed Jacket + Cream Henley.** Olive waxed jacket over a cream henley with brown leather boots.

\"Blue — **Blue Dress Shirt + Navy Blazer.**

Straight off-white linen pants

\"Dusty — **Dusty Rose Polo + Tan Espadrilles.**

\"Sage — **Sage Camp Collar + Tan Loafers.**

Linen wrinkles. That's the whole thing with linen — you just accept it. Off-white is easier than pure white because you don't look like a cruise ship entertainer. Fit matters here though. Too much volume and it stops looking intentional. And don't wear a pure white top with these. The slight tone difference between white and off-white just looks like you failed at matching.

Straight olive green chinos

\"Tan — **Tan Chore Coat + Work Boots.** White pocket tee, tan chore coat, and brown boots.

\"Tweed — **Tweed Sport Coat + Cream Cable Knit.**

Olive + burgundy + cream might be my favorite combination in this whole thing. Olive just goes with everything — navy, camel, rust, white.

Shorts

\"Linen — **Linen Camp Collar + Sandals.** Light blue camp-collar linen shirt with khaki shorts.

\"Pastel — **Pastel Polo + Boat Shoes.** Light pink polo with khaki chino shorts.

Winter layering rules

After reading way too many winter-style threads and watching too many layering videos, the same rules kept showing up:

Start thin. Tee, henley, OCBD, merino crewneck. Two lighter layers under a coat almost always look better than one huge sweater doing all the work.
Let the coat decide the mood. Overcoat and peacoat read smarter. Field jacket, chore coat, waxed jacket, puffer read more casual.
Texture saves boring colors. Charcoal, navy, olive, cream, black all work better in winter when one thing is chunky, one thing is smooth, and one thing looks a little rough.
Boots do a lot of the heavy lifting. Chelsea boots, chukkas, lug-sole derbies, combat boots. Sneakers can work, but boots make cold-weather outfits look finished.
One loud thing at a time. Big flannel, rust knit, burgundy sweater, patterned scarf — pick one and let everything else stay quiet.

Quick reference

Made these for myself because I kept forgetting what goes with what at 7am.

Color pairings

\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n

Bottom	Best top colors	Avoid
Dark blue jeans	White, grey, black, navy, burgundy, pink, olive	Orange, bright blue
Light blue jeans	Navy, white, burgundy, olive, brown, cream	Light grey, light pastels
Black jeans	White, grey, olive, burgundy, camel, bold colors	Navy (too close), brown shoes
Khaki chinos	Navy, white, emerald, burgundy, light blue, pink	Yellow, gold, beige tops
Off-white linen	Navy, light blue, dusty rose, sage, tan	White, black
Olive chinos	White, navy, camel, cream, burgundy, rust	Bright green, neon
Shorts	White, navy, grey, pastels, linen textures	Dress shirts, heavy layers

Footwear pairings

\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n

Bottom	Casual	Smart-casual	Avoid
Dark blue jeans	White sneakers	Brown boots, loafers	Dress shoes
Light blue jeans	White sneakers, canvas	Brown boots, tan loafers	Black shoes
Black jeans	White or black sneakers	Black boots, black loafers	Brown shoes
Khaki chinos	White sneakers	Brown loafers, suede boots	Hiking boots
Off-white linen	Espadrilles, canvas	Tan loafers, woven leather	Heavy boots
Olive chinos	White sneakers	Tan or brown loafers, chukkas	Black sneakers
Shorts	Canvas sneakers, loafers	Espadrilles, boat shoes	Dress shoes, boots

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