My outfit library

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

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

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

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

Navy peacoat and cream cable knit — **Navy Peacoat + Cream Cable Knit.** Navy peacoat, cream cable-knit sweater, light blue oxford shirt, dark brown boots.

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

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

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

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

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

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

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

Baggy dark blue jeans

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

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

Black puffer and grey hoodie — **Black Puffer + Grey Hoodie.** Black puffer jacket over a grey hoodie with black chunky boots.

Olive quilted liner and cream sweatshirt — **Olive Quilted Liner + Cream Sweatshirt.** Olive quilted liner jacket over a cream sweatshirt with dark brown work boots.

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

Canvas chore coat and work boots — **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

Navy polo and white sneakers — **Navy Polo + White Sneakers.** Navy polo shirt with white leather sneakers.

Burgundy crewneck and brown boots — **Burgundy Crewneck + Brown Boots.**

White linen shirt and tan loafers — **White Linen Shirt + Tan Loafers.**

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

Olive bomber and white tee — **Olive Bomber + White Tee.** Olive green bomber with white canvas sneakers.

Brown leather jacket and brown boots — **Brown Leather Jacket + Brown Boots.**

Cream cable knit and tan boots — **Cream Cable Knit + Tan Boots.**

Navy peacoat and cream fisherman sweater — **Navy Peacoat + Cream Fisherman Sweater.** Navy peacoat over a cream fisherman sweater with dark brown 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 tee and canvas sneakers — **Striped Tee + Canvas Sneakers.** Navy-white striped tee with white canvas sneakers.

Dark denim jacket and white tee — **Dark Denim Jacket + White Tee.**

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

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

Straight black jeans

Grey blazer and black chelsea boots — **Grey Blazer + Black Chelsea Boots.** Charcoal blazer and black tee.

Olive bomber and black boots — **Olive Bomber + Black Boots.**

Taupe cardigan and black chelsea boots — **Taupe Cardigan + Black Chelsea Boots.** Taupe shawl-collar cardigan over a black mock-neck knit.

Charcoal topcoat and grey crewneck — **Charcoal Topcoat + Grey Crewneck.** Charcoal wool topcoat over a mid-grey crewneck with black derby boots.

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

Black turtleneck and chelsea boots — **Black Turtleneck + Chelsea Boots.**

Grey merino and black puffer vest — **Grey Merino + Black Puffer Vest.**

Camel overcoat and black turtleneck — **Camel Overcoat + Black Turtleneck.**

Burgundy sweater and black chelsea boots — **Burgundy Sweater + Black Chelsea 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

Oversized black tee and chunky sneakers — **Oversized Black Tee + Chunky Sneakers.**

Flannel shirt and black boots — **Flannel Shirt + Black Boots.** Red-black flannel open over a white tee.

Shearling jacket and charcoal hoodie — **Shearling Jacket + Charcoal Hoodie.** Dark brown shearling jacket over a charcoal hoodie and black combat boots.

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

Charcoal cropped puffer and cream hoodie — **Charcoal Puffer + Cream Hoodie.** Charcoal cropped puffer over a cream hoodie with black chunky sneakers.

Cream sweater and black overcoat — **Cream Sweater + Black Overcoat.** Oversized cream knit under a long black coat.

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

White OCBD and brown loafers — **White OCBD + Brown Loafers.**

Emerald tee and tan boots — **Emerald Tee + Tan Boots.**

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

Charcoal topcoat and burgundy sweater — **Charcoal Topcoat + Burgundy Sweater.** Charcoal wool topcoat over a burgundy lambswool sweater with dark brown boots.

Blue dress shirt and navy blazer — **Blue Dress Shirt + Navy Blazer.**

Burgundy flannel and brown boots — **Burgundy Flannel + Brown Boots.**

Cream cashmere and suede loafers — **Cream Cashmere + Suede Loafers.**

Rust knit polo and white sneakers — **Rust Knit Polo + White Sneakers.**

Pink oxford and brown loafers — **Pink Oxford + Brown Loafers.**

Straight off-white linen pants

Blue linen shirt and tan loafers — **Blue Linen Shirt + Tan Loafers.**

Navy tee and white sneakers — **Navy Tee + White Sneakers.**

Dusty rose polo and tan espadrilles — **Dusty Rose Polo + Tan Espadrilles.**

White linen shirt and tan blazer — **White Linen Shirt + Tan Blazer.**

Navy linen blazer and cream polo — **Navy Linen Blazer + Cream Polo.**

Olive camp collar and navy slip-ons — **Olive Camp Collar + Navy Slip-ons.**

Sage camp collar and tan loafers — **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

Camel crewneck and brown boots — **Camel Crewneck + Brown Boots.**

Navy henley and tan loafers — **Navy Henley + Tan Loafers.**

Charcoal overcoat and oatmeal rollneck — **Charcoal Overcoat + Oatmeal Rollneck.** Charcoal wool overcoat, oatmeal rollneck sweater, dark brown suede chukkas.

Navy peacoat and cream sweater — **Navy Peacoat + Cream Sweater.** Navy peacoat over a cream crewneck sweater with dark brown boots.

Camel balmacaan and navy crewneck — **Camel Balmacaan + Navy Crewneck.** Camel balmacaan over a navy crewneck sweater with dark brown suede boots.

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

Burgundy crewneck and tan bomber — **Burgundy Crewneck + Tan Bomber.**

Tweed sport coat and cream cable knit — **Tweed Sport Coat + Cream Cable Knit.**

Rust overshirt and tan tee — **Rust Overshirt + Tan Tee.**

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

Shorts

White polo and canvas sneakers — **White Polo + Canvas Sneakers.** White polo, navy chino shorts, and white canvas sneakers.

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

Fitted tee and loafers — **Fitted Tee + Loafers.** Grey fitted tee with olive chino shorts and tan loafers.

Pastel polo and boat shoes — **Pastel Polo + Boat Shoes.** Light pink polo with khaki chino shorts.

Pink linen shirt and cream shorts — **Pink Linen Shirt + Cream 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

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

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

My outfit library

Straight dark blue jeans

Baggy dark blue jeans

Straight light blue wash jeans

Baggy light blue wash jeans

Straight black jeans

Baggy black jeans

Straight khaki chinos

Straight off-white linen pants

Straight olive green chinos

Shorts

Winter layering rules

Quick reference

Color pairings

Footwear pairings

Home workout plan

My meal plan

Comments

My outfit library

Straight dark blue jeans

Baggy dark blue jeans

Straight light blue wash jeans

Baggy light blue wash jeans

Straight black jeans

Baggy black jeans

Straight khaki chinos

Straight off-white linen pants

Straight olive green chinos

Shorts

Winter layering rules

Quick reference

Color pairings

Footwear pairings

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Home workout plan

My meal plan

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