Wearing Hats With Tailoring

If you were asked to visualize an individual wearing a suit and hat, typically, the image of a fedora, or some form of felted-brimmed headwear automatically comes to mind. That should not surprise you, as these were often worn in conjunction with tailoring throughout the 20th Century and portrayed correspondingly in movies/TV shows.

I think hats are very useful, and sometimes stylish, but I have never taken a liking to brimmed hats as it doesn’t suit my face shape well. Believe me, I have tried just about every other model at Goorin Bros on numerous occassions and could not find one that I was wholeheartedly satisfied with. Additionally, wearing a brimmed hat feels unnatural to me as it isn’t congruent with my wardrobe or lifestyle.

Hats can come in handy if you have a bad hair day or have absolutely no desire to fix your bed hair. If brimmed hats are not your style, there are other unconventional headwear substitutes to consider: Dad hats or a beanie. Before we continue, please bare in mind that these two options are inherently casual and I do not foresee, nor recommend, it complimenting a formal outfit (for example: a navy suit, silk tie, white shirt, navy tie and oxfords – corporate attire essentially).

Dad Hats:

Out of the two, the Dad hat is substantially easier to pair with tailoring. Dad hat is a type of baseball cap that is defined by its curved brim. What I personally like about the Dad hat is its ability to provide an additional visual interest to the ensemble and/or, in certain circumstances, harmonizes the ensemble by making it more casual. For an instance, looking at the photos (below), the medium washed denim Dad hat is paired with a chambray button down, indigo herringbone linen/wool tie, double breasted navy blazer, stonewashed jeans and burgundy penny loafers. Without the hat, this pairing would be viewed with perplexity as the blazer/shirt/tie combination leans toward the formal aspect while the stonewashed jeans to the other. The Dad hat then acts as an anchor, docking the ensemble closer to the casual lane of the formality spectrum.


Jacket: SuitSupply \ Shirt: Spier & Mackay \ Brown Leather Braided Belt: Ralph Lauren \ Tie: Bows-N-Tie \ Stonewashed Denim: Club Monaco \ Herringbone Socks: Anonymous Ism \ Shoes: Weejun Penny Loafers \ Pocket Square: Drakes \ Dad Hat: Gap 

For versatility sake, one in medium/light blue or olive would be the most ideal. The one from the photo is from Gap, which you can easily score from their frequent 40% off sales. You can also find one in a seasonal fabric, like this wool hat from Brooks Brothers or brown houndstooth tweed from Ralph Lauren.


I have been wearing this double breasted jacket a lot recently. Despite the generous swooping expressive lapels, the navy base pairs exceedingly well with everything in my wardrobe. It is also incredibly comfortable due to it’s lack of shoulder padding and being completely unlined (read more about the jacket here).


In recent years, stone/lightwashed denim have received a lot more attention, particularly for having a “Dad” affiliation. However, the stonewashed denim shouldn’t be confined to your father’s wardrobe and, in a contemporary silhouette and paired adequately, can potentially appear youthful.


Stonewashed jeans are so inherently casual that it feels a little unnatural to pair it with tailoring. I found it more appropriate to wear it with a black leather or quilted jacket. However, if you intend to use tailored garments, team it with a navy jacket. This neutralizes the jeans, allows you to create a stronger contrast and avoids over pale-ing you out.



As you may be aware, I am not a large user of black and usually opt for navy, grey or brown as my “safe” colours instead. However, this black beanie, holds an exceptionally special place in my wardrobe. I purchased this beanie in 2010 from a local Singaporean vendor. The construction is barely passable and the fabric’s a weak cotton/polyester blend.  Still, throughout the years, I have worn this beanie for B-Boying, dates or just to keep hair out of my face. The memories encapsulated in this beanie, and the emotional attachment it harbours, is one of the most significant reasons I love clothing.


Beanie: Unknown \ Sweater – Gap \ Blue Cotton Pique Shawl Collar Jacket: J.Crew \ Pocket Square: H&M \ Trousers: Made-To-Measure \ Shoes: Mr. B’s

Personally, I like to wear my beanies a little higher up on my forehead and have the crown flapped over as I feel the most comfortable in this style. You don’t have to wear it like this, rather do whatever comes the most naturally to you. Beanies are so underused that we often forget the functionality it provides, namely warmth. It’s one of the few accessories that really looks great with anything and doesn’t require much thought to pair. Late to meet a friend? Some of my favourites: ribbed cotton knit from H&Mnavy cashmere from Club Monaco or cookies & cream lambswool donegal from Drakes.


The beanie is pair here with a blue herringbone flannel trouser, cookies and cream sweater and a shawl collar cotton pique jacket, which I have taken a particular liking to. It fits exceeding well for one that hasn’t been altered – miraculous for someone in a lengthy skinny frame. The jacket has no shoulder padding, a fuller chest, denser/heavier fabrication and a lower single button stance, which adds to a visually trimmer waist.


I typically pair this jacket with black jeans, black turtleneck and black Chelseas for the night out. But I also like wearing it casually, with jeans/chinos and a scoop neck tee. The purchase of this jacket was meant to be versatile enough for casual and formal ensembles, and it’s also no secret that I love using formal clothing in a casual context. Some will frown upon it. But, if it’s any consolation, The Rake actually has something similar at the moment called Blazedo, in worsted wool and patch pockets. It’s very expensive and personally a highly questionable investment, but it’s reassuring to know that a celebrated Classical Menswear publication also advocates the use of shawl lapels casually.


These looks, particularly the ensemble with the beanie and shawl collar jacket, may appear silly, clownish or inharmonious, and it’s acceptable if you feel this way. Dressing is a form of expression that is supposed to make you feel comfortable and confident, as opposed to social acceptance or validation. Ultimately, try mixing a Dad hat or beanie if it appeals to you. If it doesn’t, take this post with a grain of salt and, at the very least, appreciate the imagery.


Thanks for reading, cheers.


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