how i dress

2026-08-20

I've been asked by a number of friends for advice on clothing and dressing well, so I decided to write up my thoughts to more easily share them around.

I am by no means a fashion expert nor a professional in the art of style. My only claim on this topic are from the compliments afforded to me by my peers, and kind strangers I've encountered on my travels.

motivation & principles

I try to focus on dressing with functionality and comfort in mind. For me, this is the top priority. In practice, this looks like clothes that afford me high mobility and comfort in a given climate.

Along with functionality and comfort, I try to make sure that there is some level of color cohesion across the entire fit. This extends beyond just my clothes, but also for accessories - bags, shades, jewelry, etc.

Lastly, drape and shape: how clothes look and hang off of the body. It's easy to both continue wearing old, ill-fitting clothes out of habit, as well as buying oversized baggy clothes in the pursuit of feeling comfy. If your goal is to dress to impress, then blindly doing these two things will work against you.

on color

Most folks who start to think about how they dress might focus more on individual garments or how an article might fit on their body, so long as the color isn't too outlandish. I find that this ends up leading to wardrobes that lean and skew mostly towards neutral colors: black, white, beige/cream, navy, a black or light-wash indigo for denim, and sometimes an accent color of personal preference. While I don't think this is inherently a bad thing, I do believe that staying stuck in thinking "I can't buy/wear this piece because the color is too loud" can prevent you from exploring clothes you might end up loving the most.

For example, I really wanted to get a barn coat, but didn't really feel like spending more than $100 at the time. As greedy of a request this was, I ended up spotting a deal on a chore coat for about ~$65 - it was in a vibrant firetruck red. I ended up trying it on in person, and it eventually grew on me the longer I wore it. With this coat, I ended up exploring more warmer colors to add to my wardrobe, like yellows, browns, and rusty orange. My most complemented outfit at the time came from wondering "what if I dressed up like a torch from Minecraft."

My point is, as you explore different options for your wardrobe, don't shy away from adding different colors to the mix. I will note out of caution that having too many starkly different colors may make it hard to match things, less you risk being compared to a pop culture reference.

My personal rule of thumb is to not wear more than 3-4 colors, and try to either match colors in either hue or saturation. As for which colors to pick, I'd recommend starting with a decent array of clothes in black, white/creme, and navy/denim, and see which of your favorite colors might start fitting together in this mix: a green button down layered over a white tee & light wash jeans, or maybe a purple crewneck layered over a white tee and black jeans. The spectrum of visible light is none but yours to explore.

on fit & drape

It took me a while to realize the importance of clothes that fit well against the body, and hang well off the body. Oversized shirts are easy and comfy to wear, but wearing shirts two or three sizes larger looks incredibly sloppy. Wearing pants that are too tight or sag low equally leaves a bad impression.

It's important to wear clothes such that your entire frame looks proportionally pleasing to the eye. For someone like me, with a long, stocky torso, my goal is to make my torso appear shorter and legs appear longer. With bigger, athletic legs, I also would want to avoid too sharp of a taper to avoid looking like a hard-boiled egg propped up by toothpicks. In my case, I choose to wear higher waisted pants to create a more stark visual separation between my legs and torso, with wider legs that keep my legs appearing at an even width throughout. I also wear shirts that are either slightly cropped or form fitting enough so they don't balloon out when tucked, as this will help keep my torso from appearing too wide. The combination of these two choices helps me dress in a way that makes me look and feel confident on a daily basis.

That being said, let's discuss the different components that make up my wardrobe.

base layers

More important than the clothes seen by other people are the clothes closest in contact to your body. Across the many hobbies in which I've dabbled, the most meaningful upgrades I've invested in are in the human contact points or interfaces - bike saddles, trackballs, guitar straps, etc. For me, the first layers of clothes I put on have the most impact on how I feel as I dress.

underwear

For underwear, I've had an incredibly difficult time searching for a pair that fit me the way I wanted - long enough to prevent riding/chafing, not made of polyester/nylon (or some other fabric that traps stink), and durable enough to survive sporty activities and hard washing.

I'm currently stress testing Duluth Trading Co's Dang Soft Extra Long Boxer briefs, and have found them to be excellent so far! They seem to survive hard washing & drying, and I've had plenty of great experiences with modal in the past.

Here's some other brands I've tried out, and why they didn't work out for me:

• Hanes Premium Stretch Long Leg Boxer Briefs: moderate durability, ended up riding up
• lululemon Always In Motion Boxer Brief 7": rides up, thin modal ended up getting holes
• David Archy: couldn't find a pair that didn't ride up, and wasn't a big fan of the fly design
• Natural Feelings Modal Boxer Briefs 9": low durability, and not enough structure to keep from riding up despite being super long
• Real Men 7" Modal Boxer Briefs: some folks online noted that a pouch would improve inner thigh chafing, but I did not find success

socks

For socks, I would usually wear them through for ~2 years before they would accrue a perpetual odor that couldn't be removed from simple laundering. I chalked this up to being made of polyester/nylon, so I decided to start looking for socks made of cotton or wool.

I'm currently settled on ascolour's Relax Socks as they're 90% cotton. I haven't had any major issues with stretching, odor, or durability, but will continue to stress test them over the next year. I've also got a few pairs of their Slub Socks, made of slightly more cotton, but these have tended to loosen quite a bit after a bit of wear. They shrink back up after heat drying, so I still wear these in my rotation.

For wool socks, I've had a good run with Kirkland Signature Men's Merino Wool Blend Socks. They're quite thick, but retain shape and hold up well after washing.

base tees

The root of my outfits start with a base t-shirt, which will usually influence what else I'll wear for the day. Since ~2018, I've been keen on minimizing branded or graphic tees I own and wear, unless I have a particular fondness for their designs.

For blank tees, I've been enjoying ascolour's Staple Tee. I'll generally reach for these during the summer, or when I'm wearing a layered outfit. As a standalone shirt, I'll wear their Classic Tee.

I've tried many blanks over the years, and have these words to say:

• Comfort Colors: nice cozy boxy fit, but suffers from a weak collar over time
• Bella+Canvas & Next Level: nice and soft to the touch, but wanted to move away from poly-blends
• Original Favorites: wore these for a while, but often struggled with how much they shrunk on the first wash

bottoms

The market for pants tailored specifically to men really sucks right now. Much of what is available suffers from one or more of these issues:

• Low rise, intended to be worn at the hips. Not an issue if you prefer this, but I have a proportionally longer torso, so this ends up making me look unbalanced.
• Pleats not available without spending a fortune. Trends have started to shift this back, but after having discovered pleats, the room and flexibility they provide me is unmatched.
• Tight thighs for many fashionable cuts. Having rode a fixed-gear bicycle for 3 years on a very hilly campus, my quads physically cannot fit pants sized for my waist - hence my praise for pleats.
• Tailored while solving the above issues, but are prohibitively expensive. I'm not someone who's willing to spend an exorbitant sum of money on individual pieces, especially during a time of my life where I'm 1. shedding a lot of weight and 2. not too rigid on my preferred niche in style. I can't justify dropping over $100 on a pair of pants I'm unsure if I'll stay satisfied in wearing 5 years from now.

My solutions to the above problems have been mostly resolved by the following:

• Losing weight. Most fashion-forward companies aren't making sizes catering to the extreme ends of the tailored spectrum. Simply bringing myself closer to the more common range of sizes gives me more options for finding clothes that look better.
• Browsing the women's pants section. These tend to have much more variety in styles and colors, along with being more reliably cut to sit high on the waist. If you're not shameless enough to browse these sections in person, consider ordering online.

pants

I've become a huge fan of UNIQLO and GU for relatively affordable and stylish pants. The pairs I have in my current rotation are:

• UNIQLO Men's Barrel Pants: pleated, and a roomy, traditional wide straight leg. High-waisted.
• UNIQLO Women's Cotton Culottes: admittedly my first foray into shopping for women's pants, I had been surprised to bump into two other friends wearing the exact same pants. Wish these had belt loops.
• GU Balloon Pants: comfy, flowy, and somehow keeps their shape full of air. Lacks rear pockets, unfortunately.
• Levi's 578: high-waisted with enough room to move while squatting or lunging.
• Levi's XX Chino, baggy: same notes as the 578s.
• Dickies Men's Relaxed Fit Duck Carpenter Pants: same notes as the 578s, but being made of duck canvas, these take a long time to wear in. Expect these to be quite stiff for a number of weeks.
• Ralph Lauren Andrew Pant: high-waisted, pleated, and lightweight. Great for office-wear, especially during the summer. This is an older product line, so you'll have to scout for these from resellers like eBay.
• UNIQLO C sweatpants: I only wear these at home in the cold. They're cut to be worn at the waist, and have hidden strings at the ankles to cinch them tight.

shorts

I've admittedly had more trouble finding good shorts that meet my criteria compared to pants. Many modern shorts have a very tight slim thigh, making it hard to maneuver around in them. Here's some that I've settled on so far:

• UNIQLO C sweat shorts: I only wear these at home, gym, or during sporty activities.
• Ralph Lauren Tyler shorts: Like the Andrew pant, but a baggier cut with a longer inseam. I personally prefer a short with a longer inseam and roomier legs.
• Land's End No Iron Comfort Waist Pleated Front Chino Short: these come in both a 6" and 9" inseam. I can never find them selling a variant of these without the comfort waist (i.e. expandable waistband), but it's honestly just a minor inconvenience with a bit of hand tailoring. These go on sale quite often, and are made with a nice, thick fabric.

tops

With the base of our outfit in place, it's nice to throw on something on top of our shirt to help add more depth, variety, and a different silhouette - aside from weather constraints.

coats

• The North Face Men's McMurdo Parka: this coat is ridiculously warm, and it's served me well in the worst of winters. This coat makes it hard to wear anything else aside from a simple shirt underneath it, however.
• Alpha Industries M-59 Fishtail Parka: this coat is nice for transition seasons - when it's too cold for shorts but too warm for scarves. I often wear this during the fall, since it doesn't protect me from spring rain.
• Muji Labo Water Repellent Hooded Coat: this has the same silhouette as the M-59 but is made of water-repellent nylon, so I wear this in the spring.
• UNIQLO C Knitted Jacket: a soft, warm wool suit-styled coat that makes for a nice option for winter-weather formal events.
• Ralph Lauren blazer: I picked up a relatively light wool-blend blazer from a clearance rack, and I often wear this as less formal option to suits of uniform color.
• Orvis Barn Coat: this coat has a nice warm flannel lining, making it a great layering piece deeper into winter. I picked this up in a bright red as it was on a steep discount, but it's definitely helped push me out of my comfort of wearing dark neutrals.

light jacket/shackets

• UNIQLO U Work Jacket: in olive, this makes for a sturdy and functional outer layer during the spring and fall. I often carry things in its multitude of pockets.
• GU Denim Work Jacket: same notes as the UNIQLO U, but in a brown denim.
• Ralph Lauren chore coat: I picked this up on a clerance rack, but it has been my most worn garment during the spring and summer months. It's light and drapey, with plenty of pockets to carry things around.
• Duluth Trading Co. Indigo Dobby Chore Coat: the dobby weave makes it feel much softer than typical denim, and the pockets are huuuge.
• GU Denim Zip Up Jacket: cropped to the waist, this jacket is a nice contrast from the longer coats I tend to wear.

dress shirts

• Land's End Sail Rigger Oxford Shirt: these are incredibly thick shirts that wear better over time. Great buttoned & tucked, or cuffed & left open to drape.
• Ralph Lauren Oxford Shirt: I owned a number of these before deciding to move more of my wardrobe to the Land's End shirts. I still prefer these for more interesting patterns, or their chambray shirts.
• UNIQLO Oxford Oversized Shirt: I bought a few of these, and enjoyed their untucked styling on the hem, but after a few months of wear, I think I prefer 100% cotton over this cotton-rayon blend, especially for oxford shirts.

warmer layers

• UNIQLO C Smooth Cotton Sweater: these are pretty comfy and inoffensive, but require a bit more care to avoid having your torso appear as a large block of color. Would recommend layering under with a button-down shirt, or a contrasting cross-body bag.
• Aran Shawl Neck Diamond Cardigan: this wool cardigan is incredibly warm and insulating, and is incredible for the value.
• Ralph Lauren Cable Knit Cotton Sweater: I think cable knit sweaters are a nice option to have for the winter months, and these fit the bill.

shoes

Shoes are how our feet interface with the ground beneath us. It's incredibly important to find and wear shoes that are comfortable for extended periods of standing and walking. Aside from a good fit, having shoes made of the right materials also helps reduce turnover and helps you wear more shoe per dollar.

sneakers

• Merrell Moab Speed 2 Goretex: I found these in a nice mix of blues, which gives these less of the appearance that most chaotically-colored trail shoes do. I picked these up after a friend who works in the U.S. Marshals Service told me trail running shoes are all he wears - they let him run and move on any terrain he needs. I however wear these as a general walking shoe when the weather doesn't seem too pleasant.
• Keen Jasper Zionic: same notes as the Merrell, but for dry climates.
• Onitsuka Tiger Mexico 66: I've worn these for almost ten years now (much earlier than the current fashion hype), and enjoy these as a low profile beater shoe. Being made of leather, they clean & polish super easily, making pairs look newer than they are.
• Converse Chuck Taylor All Star 2 High Tops: I've had these for an incredibly long time because they're unfortunately discontinued. I'll whip these out as a gym shoe option, or if I think they'd compliment my outfit.

less sneaker-like

• Clarks Wallabees: I have these in a brown leather, as well as a multi-color raffia weave. The moccasin toe is comfy, and the crepe soles are very comfortable.
• Dr Martens 3989 Brogue Shoes: These are admittedly my dad's shoes. He'd apply a thick shoe polish across the entire shoe to give them a deep shine, as well as to hide the yellow stitching, portraying them as a much dressier shoe. I continue the tradition.

boots

• Redwing Heritage 8146 Roughneck: I've wanted a pair of nice, leather boots for a while. After trying the Iron Ranger in store, I found myself more fond of the moccasin toe on the Roughneck.
• Timberland Pro: I got these for $20 on some ridiculous sale, so I wear these solely for doing work in the snow.

accessories

After settling on a consistent wardrobe, I found myself looking for other ways to ~spend money~ improve the look of my outfit. Beyond clothes, the next rational step was to accessorize.

rings

• Clocks & Colours Ego Death: this ring was a gift from a friend who thought I could use a nice ring to match my personality. This ended up being my first foray into jewelry, but a welcome one.
• RFID tag: I bought a ring that holds an embedded T5577 tag, which I often use to get into my housing complex, but will sometimes reprogram it to a friend's keyfob if I'm spending a few days over.

neckwear

• .925 sterling silver chain: I bought this a while ago but felt it was too short to wear. Eventually, I decided to just wear it, and realized the length was perfect.

wristwear

• Apple Watch: I original had a Pebble watch solely to be responsive to texts and phone calls (mainly from parents). This smart watch habit eventually led me to adopting the Apple Watch as part of my daily equipment.
• Seiko 5 Sport: I wanted a mechanical watch I could wear as an alternative to my Apple Watch, and Seiko 5's are a great option. I've had many watch people come and ask me which watch this was, despite being quite a common first-buy in the hobby. I suspect the dive bezel confuses many into thinking that it's a Submariner or something.

bags

• UNIQLO Round Shoulder Bag: I wear this as a sort of "extra pocket." It's relatively inoffensive, and comes in many colors.
• UNIQLO Utility Shoulder Bag: I wear this when I need to carry more things than just a wallet and keys - book, camera, etc.

conclusion

I hope these musings may help the friends who've asked me about exploring their own personal style, and whomever else may stumble upon these writings. I'd recommend not trying to adjust everything at once, and to consider your current wardrobe to see what things you like - either to keep, or as an inspirational direction towards the kinds of outfits you'd like to wear soon. Above all, make it fun to dress, for you feel best when you enjoy how you're dressed.