Motif socks can be difficult to pull off. There are a few pitfalls. To speak in plain terms, it is extraordinarily easy to come off as a dweeb, a dork. Unless you have the right attitude, presence and general approach to style, it can look dork-ish. It can look as if you are a little boy. It can be childish. There is no simple, clear key to avoiding this. There are different factors that impact different men in different ways. I would say in the most general terms, in order to not look like a dork or a child, you need to have a general approach to style that is more serious, steady and adult. If you tend day-in, day-out, to err on the side of seriousness in your outfits, if you tend to have a clearly serious, heavy, direct presence, the rare occasional motif sock appears like a nice little holiday. It compliments your outfit and general style wonderfully like a holiday compliments us after too many hours of toil.
Often if you are too buttoned up, too intentional, too tightly wound and put together, the motif socks exacerbate a feeling of being over done. It will feel as though you are too fastidious, too particular. It becomes almost odd. It is a little off. It is the opposite of sprezzatura. Sprezzatura gives you a feeling of nonchalant elegance. You get a feeling that the outfit was just thrown together without too much thought. Even if there was a great deal of thought, it feels as though there wasn't. This feels approachable and natural. The feeling and sense of being too buttoned up with motif socks added on top is the opposite of sprezzatura. It gives off the air that you tried too hard.
Another problem is busy-ness. The motif socks are extraordinarily bold considering they are socks. To have a motif on a tie is not considered extraordinarily bold because ties often have motifs and elaborate patterns. Socks, not so much. When you have a motif on a piece of clothing you are hoping that the eye will be drawn toward that piece. The motif socks draw the eye downward. Plain bold socks do this same thing. Motif socks do so even more. If you have a bold tie, patterned sport coat and motif socks, it is too much. You have so much going on. The eye has no idea where to look, what to see. It is too much. It is confusing and a bit clown-like.
So, what is the solution? Simplicity and informality. Let the motif socks take the reins. Get everything else out of the way. Notice the photos above. Everything else is neutral and out of the way. Stone chinos, roomy relaxed white OCBD with the sleeves rolled up, oxblood loafers. If I wanted, I could put a navy blazer over the white OCBD without any damage done. No tie. When someone sees me in this outfit (with or without navy blazer) the socks are clear and obvious, they appear as a delightful flourish among an otherwise entirely simple, uneventful outfit. You want to provide a plain canvas for your socks to appear.
Informality is key, just like simplicity. To avoid the feeling of being too put-on, too intentional, too buttoned up, keep things informal. Forget the tie, maybe forget the blazer, the sport coat. The motif sock will work best in this most casual, informal approach. In this totally casual place, the outfit feels natural and as if it was put together without any overthinking. Bringing the motif socks into this place of relaxed nonchalance allows the choice of these bold socks to even feel carefree themselves(!), as if one just grabbed them without thinking too much and threw them on. In this way you are able to de-stigmatize the motif sock. You are able to steer its energy, essence and appearance away from intentional and into unintentional despite the extremely intentional path which brought you here.