The Tomboy’s Guide to Dressing Better


 

At the tender age of four, you stole your father’s enormous ballcaps and wore them backwards, sulking when the adults around you called it cute. At ten you disdained shirts with butterflies and dolphins and drifted towards shirts with dogs and orcas. When highschool hit, you coveted loose cargo shorts and oversized sweatshirts, or did your best to pull off denim vests. Boys’ jeans were a staple of your wardrobe, and girly was a dirty word.

These days, maybe you’re a hoodies and graphic tees kind of person. You’ve learned that when the occasion calls for it, you’d rather rock a suit than a dress, and maybe you’ve got some key items like a pair of oxfords and some nice ties that make you feel proud and powerful. But there’s still something missing – you can’t wear your secret agent tux everywhere, even though it makes you feel like you’ve got the world in your palm when you do have the opportunity to crack it out.

But what about your everyday? Does your wardrobe leave you feeling uninspired, maybe a little awkwardly juvenile? Hoodies and jeans and graphic tees are great if that’s your thing, but perhaps there’s a voice inside of you that wishes there was a way to look a little more dapper in your day-to-day. The thing is, you’re not sure where to start. What middle ground is there for a tomboy who wants to feel good when they step out the front door?

If you feel there’s something missing when you catch your reflection in a store window, maybe it’s time to upgrade your style. You’re not in school anymore, so it’s time to take your look from sleep-deprived undergrad to confident, well-dressed adult. And we’re here to help.

 

Step One: Give Yourself Permission to Let Go of Clothes That Don’t Make You Feel Amazing

Take a look at your wardrobe. Really look at it.

There are undoubtedly a few pieces in there that you’re holding onto because of misplaced fashion guilt. You bought that shirt and never wore it. Those pants don’t really fit the way they used to. You were given that shirt as a gift and you don’t feel right getting rid of it.

It’s time to absolve yourself. It’s okay to get rid of things you never wear, or only wear when you haven’t done laundry in three weeks and the pickings are slim. In fact, it’s more than okay – it’s essential that you do.

So, the first step to mastering and levelling up your fashion game, dear tomboy, is to find all the things you own that you don’t love wearing. All of them – even if you have to empty your closets and make an afternoon project of sorting your entire collection of clothing into “yes” “no” and “sigh” piles. Think of it as a purging before you begin building yourself back up again.

Put aside that old graphic T that your ex bought you all those years ago that you kind of like but have too many weird feelings about to ever wear. Excavate that weird button up with the collar that never sits right that you wore to your cousin’s wedding once. And yes, those cargo shorts you loved when you were seventeen – they don’t fit anymore, and that one pocket has a hole. There will be other shorts, better shorts, and you’ll thank yourself for opening your heart to new options.

Give them to little cousins who want hand-me-downs, or drop them off at a local charity that takes clothing. It will be deeply cathartic both for your sense of self, and is the first essential step for feeling better about the person you see in the mirror.

 

Step Two: Don’t Get Hung Up on Gendered Inspiration – If You Like It, You Can Rock It

Gender can be a weird thing to navigate for people who are looking for stylish inspiration but don’t fit into the traditional buckets of gendered threads. There are a lot of cruel opinions out there about what people should and should not wear, and what sort of undesirable you’ll look like if you wear a certain thing.

Whether you came to this page because you’re a tomboy, a non-binary person, or a trans man, there is no doubt that you’re loaded with fears and notions about how people will perceive you. Many people go their whole lives bracing themselves for the dreaded phrases “that makes you look like a man” and “that makes you look like a woman” – it can be infuriating to try to navigate fashion when style guides tell you brogues make you “mannish” and v-necks make you “effeminate”. We’re not about that.

Take a deep breath, and imagine a world in which you’re allowed to like whatever clothes excite you. Try to hold on to that mystical place when you see something that looks nice. When your sense of style teeters somewhere in the middle, it can be easy to tell yourself you’re not allowed to like something if it’s too feminine or too masculine. Trust in your own personal preference, and ignore the nagging voice of judgement in the back of your head. If you want to be handsome, you get to be handsome. If you want to be beautiful, you get to be beautiful.

Ultimately, you are the presiding expert on what high class fashion trends appeal to you. Whether the person wearing that style you feel inspired by identifies as male, female, or neither is irrelevant to the fact that it speaks to your inner self. You get to decide what kind of awesome you want to emulate.

 

 

Step Three: Buy The Basics to Lay Your Foundation – Build Your Core Wardrobe

Time to get to the fun part – shopping. In fashion, there’s a concept called a “capsule wardrobe” that basically just means a handful of some foundational items that all pair well with each other. Think of it like buying groceries that work as ingredients for like four different meals when combined together in different ways. You want to start your style reinvention by making a capsule wardrobe of eight key items.

The below list is what’s often considered fashion Must Haves, but feel free to add or leave out items. The most important thing is that everything in your capsule wardrobe can be worn with anything else in the wardrobe, and that they’re all relatively neutral. The idea behind this is that it gives you a classy looking canvas that you can wear as-is and feel confident you look good, but that you can also top off with a more dramatic statement piece without worrying your look is too cluttered.

 

The Dapper Tomboy’s Wardrobe Foundations Shopping List
White shirts (short sleeved, nice quality, neckline to taste)
Dark blue jeans (almost black – the darker, the more formal)
Grey sweater (solid color, no patterns, thickness and style to taste)
Navy blazer (the sleeve should come no lower than your wrist joint)
Beige chinos (anywhere in the range from camel to coffee works)
Pea Coat (grey, navy, or brown, for fall and winter wear)
Dark brown derby shoes (leather or vegan leather, matte and not shiny)
Dark brown belt (leather or vegan leather, matched to your shoes)

 

These items should all be solid and neutral – again, this is about creating a base upon which you can add one or two flourishes. These eight items equip you to get started on your journey to being a well-dressed, finely aged version of your younger self – still true to your sense of style and your sense of self, but just a little more grown up. This is the middle ground before you get to the point where you’re wearing button-ups and suit jackets and pressed pants – you won’t feel weirdly overdressed or weirdly underdressed when you’ve got these simple staples ready to go.

For every one of the above on the list, there’s wiggle room in terms of the cut, the neckline, the fit – these are the swatches for using as a guideline, but ultimately whether you prefer your clothing to be from the women’s section or the men’s section – or you’re lucky enough to have stores that don’t bother distinguishing between the two – is up to you. You can still have the perfect capsule wardrobe without having to sacrifice wearing only clothes that make you feel comfortable.

With the capsule wardrobe created, you can start expanding based on things you see that you find yourself wanting, whether that’s a bright accessory, some patterned shirts, or a more fun color of shoes.  You have the essential foundation to build upwards and outwards according to what speaks to your most dapper self.

 

Step Four: Learn to Love the Local Tailor – Fitted Doesn’t Have to Mean Feminine

Have you ever looked at a candid celebrity photo where they were caught going to the grocery store in a pair of jeans and a plain white t-shirt, and you think to yourself: “How in the heck do they look so beautiful and put together in even that?” The answer is tailoring. A surprising number of celebrities have absolutely every piece of clothing they own custom tailored for their bodies after it’s been purchased.

Now, we’re not about to suggest you try to do the same. That would get pretty expensive, pretty quickly. However, having pants professionally hemmed or a nice shirt taken in is not something you should only do for the most special of occasions. Often times the difference between a suit that looks fantastic on you and a suit that looks bulky and unflattering is a quick adjustment by a tailor.

It’s important to clarify here that folks who have bodies that would be considered female may be made nervous by this idea. You think – or you worry – that it will mean the tailor turns your handsome masculine blazer into something pinched and feminine that you specifically avoided buying in the first place. This is an understandable fear, as well as the fear of “tailored” meaning “tight”, but we promise that’s not what we mean.

Think about going to the tailor the same as going to a hairdresser. You can go to a barber who specializes in men’s haircuts in the same way that you can go to a tailor who specializes in men’s suits, if you’re willing to hold your head high and be unfazed by any awkwardness on their part because they’re not sure what to make of your style decisions and whether they consider them “appropriate” for your gender. That can be scary, but you can check reviews online to see if it sounds like they’ll just roll with it. You can also ask around for recommendations – like a good hairdresser, a good tailor will have happy clients who are all too eager to recommend them. It’s worth noting that if you get a referral from a professional’s existing customer, you should mention it when you go in. It holds them accountable not just to you but also to your friend who referred you, so they’ll be more likely to make sure to treat you right to retain double the business.

If going to a specialist doesn’t seem necessary, there’s no reason not to drop in to the generic tailor in your local mall, especially for small easy tweaks on less expensive items. Like with a haircut, go in with a clear description of what you’re going for (“the shoulders are a little big on me right now, so I want them taken in, but I don’t want them too tight or feminine; I really like how strong it makes my shoulders look”) and don’t be afraid to say no to any suggestions you think would make the end result a little too femme for your tastes. You may want to bring a buddy just to keep you calm, and to help you stand up for yourself if you’re habitually too polite to say no to things you’ve been talked into.

Tailoring is really the difference between a B+ look and your ultimate A+ look – that outfit that is super comfortable and makes you feel like a million bucks. We can’t all afford to have every piece of clothing we own custom-tailored to our bodies, but it can be a dependable way to take a great off-the-rack find and really, truly make it yours in a way that elevates you.

 

Step Five: Yes, You Are Worthy – Extinguish The Doubt That You Deserve Nice Things

 This last step may be the most important step. If you feel trapped by the contents of your closet, if you look wistfully at the silent, unmoving swagger of a well put-together mannequin, and believe that you’ll never be able to pull those clothes off – well, you’re wrong.

Different people with different bodies can face a lot of obstacles when it comes to assembling the wardrobe they wish they had. Oftentimes, it’s simply not as easy as just believing you should have nice clothes, and then getting them. Barriers like a lack of size ranges or the sheer cost of “nice” clothing are not to be laughed at, and we’re not going to pretend they don’t exist.


We encourage you, however, to consider whether you yourself are presenting an additional barrier. Do you doubt that you should wear those clothes? Do you worry you won’t actually look like the mannequin? Maybe you’re afraid you’ll look foolish?

It’s okay – you’re not alone. There are hundreds of thousands of people out there who struggle to believe that they’re already worthy, and always were worthy, of any of the clothing they aspired to.

You are worthy, and always have been. If you’re toying with upgrading your tomboy’s wardrobe to something a little more dashing, elegant, and mature, we want to affirm that you do deserve to look fantastic. So squash the notion that the right to wear something has to be earned. Go buy that dapper dinner jacket you’ve always wanted. Get yourself some pants that make you feel like you just sold your tech startup for ten million dollars. You are fantastic – now go get yourself a wardrobe to match.


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