On Developing an Expressive Personal Style

I think that among those who take an active interest in fashion, we have all at some early point in our development of that interest experienced the phase of being obsessed with investing in versatile basics and staple items; justifying buying more expensive items because they’ll last a lifetime, and they’re classics that’ll never go out of style! Of course, this inevitably leads to everyone curating the same wardrobe of “timeless classics” – a blue OCBD or three, chinos in various earth tones, a pair of raw denim jeans, and of course some versatile white sneakers.

For many, this is enough – they’re dressing better than the general population and can start paying more attention to the more important things in life, like talking to other people and going outside. But for the rest of us, boredom eventually sets in. We might be dressing “well”, but that isn’t enough – we want to express our, er, incredibly unique individual tastes through the way we dress; to develop a more personal style.

For some, developing a personal style entails choosing from a shopping list of “standard” styles and pigeon-holing oneself into one, or, for the truly individual, some kind of hyrbid of them (“I dress in a streetwear style but with an Americana flair”). However, this is still more or less the same problem as before – you might have a wardrobe of clothes that work together in a cohesive way, but the only real creative input you’ve had is picking which preexisting aesthetic to go for. You’re picking a team rather than forming your own.

But exactly what kind of team are we looking to form? You want to find an aesthetic that is both internally consistent (different outfits look like part of the same cohesive whole), and consistent with you  (said cohesive whole should align with your personality or tastes or whatever). It should also be broad or diverse enough that you can adapt how you dress according to the context, weather, or required formality level, as well as simply to your mood on any particular day – while retaining some sense of a consistent stylistic identity.

A Solution

So how does one realise this deeply pretentious worthy goal? As with anything, I have no doubt there are countless ways of going about it, of varying effectiveness and efficiency. What follows is simply the path I went down, which I have found to be enjoyable and effective. By the nature of this topic, the details will vary between people, but I feel that there is an underlying core that applies generally.

The first step, perhaps surprisingly, is to completely ignore the need for diversity across different contexts; find a stylistic formula restrictive enough (even to the point of being literally one outfit) that absolutely everything within it perfectly embodies your core aesthetic ideals. For me, these ideals are clean lines, uncluttered, minimalistic details, and avoidance of garish colours or patterns. This led me towards the “formula” that defines the prototypical outfit of the “Dressed By The Internet” style: black leather jacket, black jeans, white shoes, white tee:


As promised, this simple formula conforms perfectly to my stated ideals. However, this wasn’t an entirely conscious process; I never sat down and wrote out what my aesthetic goals were and then found a style to fit it. Rather, I discovered this style, and I now retrospectively realise what attracted me to it. This is part of what makes this stage so useful – you might not know precisely what you want, but you have a know-it-when-you-see-it response to your chosen formula, so you can use it as a sort of by-proxy indicator when evaluating other options.

Now at this point you have at best a few outfits that all look good, but also all look more or less the same. Now we need to introduce some variation into the mix. Doing this is a very natural process, but it’s somewhat difficult to explain in words; as such, I’ll give it a half-assed brief attempt, but I’ll try to illustrate my point more clearly with a number of examples from my own wardrobe. In essence, you take your restrictive “baseline” style as described above, and try to “stretch” it in the direction you desire. This could mean overemphasising a particular aesthetic element, or incorporating influence from another style, or conforming to particular contextual requirements, or whatever. The word “stretch” here isn’t particularly well-defined, but the idea is that the result of “stretching” should be an outfit that looks… consistent with the original, while still having a unique twist or difference over it.


This outfit is the result of emphasising the streetwear influence in the baseline, pushing towards a more casual, comfortable style. The MA-1 bomber jacket is a streetwear staple, but keeping it black maintains the subdued, monochrome colour palette, and superfluous details are avoided, keeping the minimalist look intact. The bomber fits a little puffy, in contrast to the very slim-fitting leather jacket, which further adds to the comfy vibe.

Going for a black tee creates a visually striking #allblackeverything effect. This in itself further reinforces the casual streetwear vibe, while also creating a dramatic contrast to emphasise the stark white sneakers, reinforcing it further.

Some other options in this vein would be switching the jeans to lightwash grey or blue, and/or the tee to grey, white, or some kind of black-on-white graphic (gotta keep it ~minimalist~ tho).









This one takes on a slightly European influence, and is particularly influenced by the Saint Laurent Paris aesthetic. The overall effect is a slightly dressier outfit, more suitable for say, grabbing some drinks at a bar.  The white sneakers have been replaced by a pair sleek black leather shoes, which naturally dresses the outfit up quite a bit. I’ve used some slim monkstraps here, but ideally I’d have used a pair of black chelseas; what is important is that they are sleek in silhouette and minimal in detail, to maintain the clean lines.

Instead of the stark black/white tonal contrast between the jeans and sneakers, we now have a more subtle textural contrast between the polished leather shoes and matte black jeans – this added subtlety is something that lends itself to the dressier look. For a slightly more casual, summery option, some tan suede chelseas would also serve.

I also switched in a striped linen tee over the plain white one. This adds some more visual interest and represents a nod to the French influence, while maintaining the clean lines and monochrome palette of the base outfit. Another option would be a navy button-down (with, like, half the buttons undone – gotta show off that single hair on my chest), for a different twist in the same SLP/European vein.







This outfit takes a nod from classic #menswear to create an outfit even more dressed up – perhaps suitable for a dinner date or something. I’ve used a T-shirt to keep it still somewhat casual, but I would’ve substituted in a white button-down if I wanted it to be dressier still. The blazer is navy, maintaining the subdued colour palette of the baseline while keeping a subtle contrast with the jeans.

The black unstructured derbies continue the “dressy but not too dressy” theme, while staying in line with the established black/monochrome vibe. I used a high cuff and no socks to broadcast my homosexuality add a bit of sprezzatura flair, again incorporating that #menswear influence, as well as adding a bit of contrast around the shoes.

If I wanted crank the formality up another notch, I could have switched the jeans for some slim charcoal dress pants, and maybe the derbies for a more structured and polished pair. All of this maintains the spirit of the original baseline, but at a drastically different level of formality.







DSC05345This fit represents a stretch on a slightly different axis to the previous few. My inspiration here was a mix of Scandinavian fashion and a “practical, outdoorsy” look. Everything except the jacket is very crisp and clean, adhering very closely to the baseline aesthetic. I then added the waxed Barbour jacket, aiming for the look of having thrown on the most outdoor-appropriate jacket for an impromptu walk in the countryside, or some such pretentious shit.

The dark olive colour of the jacket plus the further darkening of the wax keeps the jacket dark and subdued, and again the detailing remains relatively minimalistic, if not quite to the same extent as the leather jacket of the baseline.

The outfit leans towards a more relaxed, casual vibe, but in a different way to the streetwear fit – it also sends something of a “pragmatic” message. Some other options in a similar direction would be switching the sneakers for some black lace-up boots, or perhaps switching the top half out for a thick sweater in off-white or grey.







DSC05379Finally, this fit is for the single warm Scottish day per year. The pale palette (#palewave) gives off a warmer, summery vibe. The lightwash jeans are faded enough in colour to maintain a relatively subdued palette, while introducing just a little colour to further contribute to the summery feel.

For an even warmer day (like, different-country warm) I might have switched the jeans for some shorts (my go-to options being chino shorts in charcoal or off-white) and perhaps the sneakers for some black-strap sandals.











I hope that my examples have been effective at communicating what I am suggesting. However, I haven’t really done much to justify why I’m suggesting it yet.

First of all, you may wonder what the point is of boiling your visual goals down to one very narrow style, only to immediately extend it back out again. Why not just directly aim to create outfits that align with your goals, instead of going via an arbitrary “baseline” outfit? The answer is that it promotes a more cohesive look or identity across different outfits. For example, let’s go back to my stated aesthetic goals: clean lines, minimalistic details, and no busy patterns or garish colours. Certainly the baseline outfit I presented fulfils these goals, but it certainly isn’t unique in this respect; consider this outfit, for example:

It more or less fulfils my short checklist, but even ignoring the formality difference, it looks totally out of place next to most of the outfits I posted above. Were I to forego the step of grounding my goals in a specific formula, I might well have chosen my earlier baseline outfit for a casual day-to-day outfit, and switched to the above for a dinner date. Admittedly not exactly the most catastrophic state of affairs, but it does subvert our goal of having some kind of internally consistent aesthetic.

On that last point, I suppose it’s worth expanding on why this is a worthy goal at all. Personally, I see my own style as almost an extension of my identity – by adapting my outfits for all occasions to this overarching aesthetic, I ensure everything I wear sends a consistent message about who I am and what I want to say. An analogy I’ve found helpful is that by foregoing this goal, you are almost dressing in a selection of different costumes for each occasion, rather than truly dressing for yourself.

Closing words

The last thing I’d like to point out is that the process I’ve outlined above, and the outfits I used, is very much the first step in a continual journey. For example, every outfit I showed has at least one item in common with the initial one – this certainly isn’t necessary (and actually wasn’t intentional), it’s just a result of me largely basing each one directly off of the baseline. As you continue to develop your personal aesthetic, you may find yourself more attracted to one “direction” more than another – for example, I really like the SLP-influenced style, while I’m not particularly enamoured with the more outdoorsy direction. You can then do some more “stretching” of the styles you like, and forge an increasingly individual path. It’s very much an ongoing process of tweaking and adaption as you gradually develop a more complete style that truly says what you want it to.

TL;DR: Find a single outfit that embodies what you like, tweak and extend from there.

If you want to see more of my outfits and other shit, follow me on Instagram: @usuallywhatimdressedin