I dress too formal outside of work, how to loosen up a bit?

Having worked in the industry for a couple of years, I found my work style leaking in to my personal life a bit. 

Now I don't wear work shirts out to bars or anything - more like collared polo t's and long sleeves, leather sneakers, chinos. 

I want to find out how to accessorize a bit, maybe go a little more street wear forward sometimes, etc. but I just feel so out of my element having been in the professional world now. 

Maybe it makes sense to start small. Curious to hear how you all dress out in the world? Before are some reference pics of the kind of stuff I wear out these days

Pocket linen shirt - Medium plane

SUITSUPPLY Californian Cotton & Mulberry Silk Black Polo

14 Comments
 

I'd suggest a good collection of casual button downs, like long sleeve linen shirts that can be worn untucked and sleeves rolled up, or short sleeved sweater polos / camp collared shirts which you can find everywhere now. I think the type of fabric is important, something more casual or with texture like boucle can help makes lighten things up from office wear. 

I'm a fan of Club Monaco, Billy Reid, Suit Supply, Todd Snyder for the aesthetic I think you're looking for. Rag & Bone's a good option that's a little more street wear leaning. A pair of go with anything sneakers like CPs go a long way as well. I personally feel with these, I can dress quite sharply on the weekends without feeling too stiff.

 
Most Helpful

Nice, think you totally got my vibe, I like a lot of the same brands. I picked up a cotton/linen blend I like to wear untucked and it opened my eyes to the casual button down game. 

Any others brands? my favorites are:

-Club Monaco, Massimo Dutti, J Crew, Bonobos, Suitsupply, Everlane, Mango

Have been eyeing Rag & Bone and Todd Snyder, will need to pick some pieces up

Also any shoe recs? I have just been rocking either chuck taylors or leather sneakers like the below, I recently got a pair of birkins that honestly go great in the summer.

Also thinking to pair up some type of accessory with my watches, just some bracelet or some small flair

 

There’s a great clothing store based in Austin called Stag Provisions which I’ve found some really good lesser known brands through. Worth checking out their site. I also love Eton for their dress shirts, but I think they have more casual stuff as well.

I personally love my common projects for shoes. Carmina is another brand I can’t recommend enough. More dressy and can be a bit pricey, but I have suede loafers and boots from them and they’re phenomenal.

On accessories, a new watch strap can actually go a long way. On my other wrist, I usually just wear this bead bracelet I got when hiking in Peru, but honestly you should just wear whatever fits your vibe there

 

Just buy a nice pair of jeans, my suggestion is Double RL which are around $350. After that you can buy some James Perse t-shirts, they fit great. Common Projects or Converse. 

 

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