Making an outfit work for two different dress codes can be a difficult task for any gentleman. Gentleman’s Box is here to help. We’ve put together a cheat sheet to making your look work when heading out of the office for weekend festivities.


This tip is for the gentleman who is a bit cautious with his choices. Perhaps you don’t feel you have the best sense of style and are looking for a guiding voice when it comes to making a look work? Well that voice is here, and it’s us. A great and really easy tip for taking your look to the weekend is simply the removal of a tie. Removing your tie and loosening your shirt a few buttons is a great way to take the formality of your outfit down a few notches. This work-to-weekend look is perfect when paired with black jeans or fitted chinos so you look casual but still office appropriate as well.   


A level 2 gentleman has his go-to pieces and knows how to pair them. Maybe you added a snazzy pocket square or some funky socks to your outfit this Friday and are looking for a way to keep this outfit interesting, but to make it more casual when heading from work to weekend. We’ve got you covered. For this look, slip on a more casual quarter zip or v-neck sweater, and a more slouchy and comfortable jacket. This takes down the level of serious while still looking sharp. Keeping simple accessories like a beaded bracelet, or a modern watch to keep you looking put together in either dress code.   


This tip is for the gentleman who is willing to take a risk, but still relies on classic pieces to make a look work. For taking this look from work to weekend, make sure you’re wearing a more casual blazer or jacket like this long-cut camel option, and simply change out your dress shirt for a nice crew neck sweater. Another great option is to take off your tie, lose a couple buttons, and layer this look with a nice knitted cardigan. This gentleman dressed his digs up with a couple of silk scarfs and some interesting accessories. We recommend adding a pop of color with some trendy dress socks as well!


If you’re not observing #FormalFriday and want to dress your look up a bit for a situation that calls for a bit more class, like dinner and drinks with a new date or just before a hockey game, then this tip is for you. At work, leave your suit jacket hanging on the dry cleaning hook in your back seat while you stay comfortable at your 9-5. You can easily switch from sneakers to dress shoes at your desk, and simply add a sleek skinny tie with an interesting design at the end of the day. Add a spritz of cologne and sport your suit coat when you get to the restaurant. Try this floral tie from our October 2015 box for a tie that’s sure to make an interesting ice breaker.


If you consider yourself the savvy dresser, this tip is for you. You already know the basics of taking your look from work to weekend, but you are ready to add a few extra touches to make you really stand out. After work, pile on the accessories. A lapel pin might not be perfect for causal Friday at the office, but it is something simple to add on while you’re on the way to meet your friends. Same goes for a great pocket square and belt. Make a statement with your accessories, so you can truly express your personal style while staying comfortable and casual. To re-create this look, pair this white lapel flower from a previous box with your blazer and a floral pocket square that ties in the colors of the rest of the outfit. We love how this gentleman slipped on some leather loafers to keep this look cool.