Fashion Q&A: Shopping for Dress Shirts


With its interactive component, our Dressing Well Blog has replaced our monthly Fashion Q&A postings. We are leaving this section of our site live so that you can have access to our Q&A archives. Each month we will feature a popular Q&A from the archives that is relevant to the season at hand.

If you have something you want to know to help pull together your wardrobe with style and confidence, ask away! We are actively seeking to make our blog as interactive as possible and will be incorporating site visitor questions and comments.


Fashion Q & A:
Shopping for Dress Shirts


Q: I’ll be shopping for dress shirts this weekend. I do not want to have custom shirts made so please do not suggest that! Any guidance as I head to the mall?

A: We call dress shirts the centerpiece of male attire. When they fit, flatter your natural coloring and frame your face well, your style soars.

Here are a few tips for shopping for dress shirts:

Get Measured
Over half the men we work with are wearing the wrong shirt size. Even if you think you’re in the correct size, get professionally measured–neck and sleeve–as a standard practice before investing in a new shirt wardrobe. You should be able to get two fingers between your neck and the collar. Tighter than that, and you’ll look uncomfortable and strained. And while you’ll certainly be more comfortable if the collar is loose, your professional presence will start to erode if the neck of your shirt is too big; you’ll look sloppy as opposed to crisp and polished. The shirt sleeve should cover the end of your wrist and extend about a half inch beyond a jacket sleeve. Like the collar of your shirt, you don’t want your sleeves to be too loose either. Play around with the buttons above the cuff, and choose to go a little tighter with the fit as opposed to too loose.

Body Fit Matters Too
Pay attention to the fit of dress shirts through the body, too. Even if you’re not super slim, fitted dress shirts are the current style and can likely be sourced in your size. We have been very successful getting our male customers who are carrying weight through their mid-section into less boxy, more flattering shirts than they thought possible given their size. Many brands offer slim cut shirts for bigger men that truly fit. Best part: a slimmer cut shirt will visually take pounds off your frame without necessarily having to go to the gym! A slimmer cut shirt also sits better under today’s more trim-fit suiting.

Wrinkle Free Options
When you wear suits, we suggest wearing shirts that are 100% cotton. Partner with a reputable dry cleaner for laundering and professionally pressing them if you’re not good with an iron. In the Boston area, we recommend Anton’s Cleaners. Non-wrinkle fabrics are a good option if you work in a business casual setting and want to launder your shirts at home.

The Details Matter
While there is certainly a wide range of shirt collars to consider, a modest “spread” collar is an easy choice for most men as it works well with both tie and non-tie looks. The “button-down” collar is the most casual of all shirt collars. In our humble (smile!) opinion, it is slightly dated to wear it with a tie and formal suiting. Pair shirts with a button-down collar with jackets, sweaters, dress slacks, jeans and khakis and wear them on days when you don’t need a tie. The shirt sleeve cuff should be loose and extend to the end of your wrist. The cuff of your shirt should extend about half-an-inch beyond your jacket sleeve.


Move Beyond White
When we shop with a client for dress shirts, we typically start with white. Blues in a variety of shades and patterns are a great first choice when adding color. Lavender (i.e. a light shade of purple) is our second favorite color to add as it looks as good with dark neutral suiting as blue does. We like certain shades of peach, yellow and tan, too, but find them a little more difficult to add as you want to be sure the tones work with individual coloring as well as core wardrobe basics – suits, jackets, pants and sweaters.

Extra Tip
Before you add any more dress shirts to your wardrobe, vow to ditch the ones that no longer fit, are stained, or are no longer needed – amen!

Scroll to Top