First of all, dispense with any phobias you may have regarding clothes shopping that are lurking around from a previous life of avoiding anything that even resembled a women's clothing store. Now is the time to enjoy your new incarnation, embrace clothes shopping and create your new image. Never again will you need to lurk sullenly in aisles of women's clothing glaring at the ridiculous shapes, sizes and inflated prices. You are now a member of the boys club where you are not expected to change your wardrobe on the whim of each new season; your clothes will now be made from durable fabrics, built to last and even withstand an acceptable amount of misuse; they will be available in a decent range of sizes; your underwear won't ride up your arse and best of all everything (except the one suit you need to invest some serious money in) will be cheaper. How good is that?
Shopping for a new wardrobe need not be expensive. Start with the basics and work up over the course of your treatment. Don't buy too much at the start as your body shape and weight will change. Then once you are fairly settled, increase your wardrobe by building on what you already have. Try to avoid items that will date or are one-offs (unless you have the budget) and aim to coordinate your purchases so that each item goes with at least three others. This way you will get as much choice and flexibility as possible from your wardrobe and your budget. If you purchase items in a cheap or discount shop, choose plain colours rather than patterns as these are not readily identifiable as coming from a particular store.
Until you feel comfortable about passing and living as a guy it is probably easier to choose middle of the road clothing styles and then develop your own personal style from there. If you are choosing clothes for work, check out what your co-workers are wearing and buy something similar. Comfort first, style second (with the exception of tracksuit pants and sheepskin moccasins which if you must own them are strictly at- home wear).
Read men's magazines e.g. FHM, Men's Health, GQ, Ralph, Loaded etc with the attention and skill of a detective looking for the murder weapon. Analyse the adverts and fashion sections looking for the main trends and then make a note of what the basic items are for the look you like. No one ever dresses like a magazine model so all you need to do is get a feel for the colours, styles, cuts and lengths. Then head to a shop or department store and try them out to see what works for you - a critical friend will help here. If you don't feel comfortable doing this in the shop, ask to take them home and do the fashion show in private. Never buy something because you are feeling uncomfortable or are being pressured by a salesperson on commission - the only people who will thank you are the Mission shop when you donate it next year.
Note: no one looks good in cubicle mirrors.
Finally if you hang around with a lot of lesbians who wear reasonably androgynous clothing, then you will need to find a way to make yourself look different from them if you want to pass as a guy. Start slowly and as your confidence increases - get bolder.
For a basic wardrobe you will need:
STARTING FROM THE BOTTOM UP:
Shoes: You may find that your feet grow slightly on T so don't invest too much in your shoes straight away. The main problem you are likely to face is that men's shoes are huge in comparison to the average FtM. This can mean that your choice of styles is limited but then again you are more likely to find something on the bargain table. Guy's shoes are bulkier in style and tend to make your feet look larger which is all good. If you have small feet try to avoid tapering styles as these will make your feet look smaller. Choose square (ish) toes (depending on current fashion) and a solid style. Initially these will feel strange and may even look a bit like clown shoes - maybe they are, so make sure you have that critical friend with you! Men's dress shoes are different and tend to feel weird for the first few weeks but you will get used to them in no time at all.
If you are on a tight budget you can either buy something cheaper and replace them after a year or invest in a good pair of slightly higher cut shoes that can be dressed up or down for both work and semi-casual. Either way you should polish them regularly as this will extend the life of your shoes. Try to buy two pair of shoes for work as it is important to "rest" leather shoes between wearing them as this will ensure that they have an opportunity to 'dry out' and last longer.
Casual shoes - go for comfort and minimalism. Look at what other men are wearing and follow like a sheep.
Avoid at all costs: grey shoes, blue shoes, white shoes, zips, Velcro (except on Vans, Airwalk or similar trendoid items), tassels and anything that resembles a golf shoe.
Elevated heel and/or heel lifts? Personally I think they just let the whole world know you have a problem with your height but it is up to you.
Socks: Black or navy coloured socks with dress shoes. White socks with sports shoes. Never swap them over. Your socks are on show every time you cross your legs so buy socks that will stay up and throw them out when they have holes or lots of pilling [the scruffy pulled bits that make your socks look hairier than your legs].
Patterns and funny pictures are a matter of personal taste and style. Remember if you want to be taken seriously at work, and you don't work in an ad agency or IT, then cartoons on your socks as an everyday item probably don't say "career ladder".
JEANS AND TROUSERS:
In general the waist on men's pants will sit lower on your body than women's pants did previously. This is a bit of a bonus as having the waistband below your actual waist will tend to minimise wide hips and thighs. Always buy pants that fit and be prepared to replace them as your shape/ weight changes. Tight pants tend to accentuate female body shapes but don't be tempted to go too baggy as this can make you look like a large rubbish bag and worse can make you look even wider in the hips and butt.
Jeans: Choose a good shop and look confused. This should enlist the services of an enthusiastic salesperson that has just been to the "Levi's (or whatever brand that particular shop promotes) can accommodate all body types" seminar - your mission is to make them prove it.
Before you go shopping, try to work out your waist and inseam sizes so that you can appear more confident. If you are not entirely sure, measure yourself roughly at home and then give a range - "I think that I am a 34/ 36 inch waist". Inches or centimetres for measurements are both fine for jeans as most follow American sizes which for some reason are in imperial measurements. The inseam is the length from your crotch to your ankle and is usually the second measurement e.g. a common measurement is 36W/34L.
If you want to hide hips and/or a more feminine body shape, choose a loose fit or wide leg style. Avoid anything too baggy as they will make you look as attractive as a sack of spuds and even make you look shorter. Once you have a pair of jeans on and they seem okay - make sure that the buttons aren't pulling (or the zip straining); check that your packer will survive the crotch seam and not end up being pushed down one leg (well not too much anyway) nor will it be squashed into oblivion; and finally, bend over and check that you can keep breathing. If all this checks out and your hyper- critical, tell-it-how-it-is friend says the butt looks good, hand over the money.
Trousers: As with jeans these are sized by waist and inseam and come in two basic styles - flat fronted and pleated. Pleated front trousers are a safe standard style that suits thinner guys who don't have any lower abdominal fat hanging on from pre-FtM days. They always look neat and can be worn casually or to work. On some body shapes, pleats hide stomach and hips but in for others they tend to flare out and make it even more obvious. Pleats come in three basic styles: reverse, box and front - the only way to find out what works best on you is to brave a session in the changing room. Again the "honest friend" can be a real bonus here. If you are not sure and don't feel comfortable standing out in the shop (it can be difficult getting a true picture in the cubicle), especially if you want to know what each style "hides", ask to take them home overnight.
Flat fronted are great on some body shapes for hiding abdominal bulges as they will sit slightly lower on you hips and hang 'flat' over the bit you want to minimise. Another trick is to avoid pockets that are sewn on an angle as these can pull, drawing attention to your shape. Most flat fronted trousers come with pockets that are sewn in line with the waistband.
If you are shorter than the average guy, avoid cuffs on the bottom of your trousers as these will make you look shorter. If you have the height, cuffs (watch for fashion trends though) help dress trousers drape better.
Ask the assistant to pin your trousers to the correct length with a break in the length where it meets your foot i.e. a bagging of the fabric on top of your shoe. This will ensure that your trousers hang properly and you don't show off too much of your hairy untanned legs when you sit down and cross your legs. Make sure you are wearing the shoes you will be wearing with this particular pair of trousers or jeans, stand still and look carefully before agreeing to a length - you can always shorten them but not vice versa.
Choose neutral colours until you have covered the basics in your wardrobe e.g. navy blue, black, charcoal grey etc. dark colours will help to make your legs look thinner, especially with a lighter coloured shirt (avoid the reverse combination even if you are tall). Avoid seasonal or trendy colours until you have some spare cash and you are ready to start establishing your own personal style.
Lastly, invest in a couple of belts - brown or black only, and wear with pants to complete the look. This can be difficult at first as a belt will emphasise the waist/hip disparity but once you can wear one it is an important part of the "office outfit".
Shirts: These are sold in three sizings: generic i.e. "one size fits all", basic i.e. S, M, L etc and by neck size for dress shirts.
The "one size fits all" really means that it will fit an average guy who usually has longer arms and torso, broader shoulders and a larger neck than the average FtM. You may get lucky but always try before you part with any cash.
Small (S), Medium (M), Large (L), Extra Large (XL) etc are easier to choose from but watch arm length and body length especially if you don't want to tuck your shirt in to your trousers/ jeans - the tent over jeans look doesn't really work. If you want to leave your shirt out then you will need to choose one with a square hem otherwise it will look untidy.
Dress shirts are sold by neck size and arm length. Again, do a rough measurement at home and ask to try the shirt on before you buy it. Most FtM's will need to buy shirts with regular length sleeves [or shorter sleeves if available] preferably with an extra button on the cuff for narrower wrists. While it can be helpful to buy a baggier/ fuller cut style of shirt to hide binding and also make your torso appear more substantial (can help to hide hips as well) don't compromise on sleeve length - too long and you will look sloppy. Never buy shirts with sleeves which are so long that when you take the cuff in you look like you are wearing a pirate's shirt - it was a bad look in the eighties and it hasn't got any better. Some shirts are also sold as slim fit - should be obvious enough.
Long sleeve only for business and if you are wondering what goes best with walk shorts and sandals then you are reading the booklet. White is a safe option but coloured shirts are widely available and acceptable in almost all work and social settings.
According to FHM magazine, plain collars generally suit thinner necks and button-down collars do wonders for thick prop forward necks. Thick necks also benefit from a collar that is not as deep and shows more neck that the regular styles. You can pick and choose between the two but remember that button-downs will make very thin necks look like pencil necks which can be a bit girly. On the other hand other magazines recommend tab collars for long necks and suggest that round/ wide faces will benefit from straight or long point collars. One thing is definite though; if you are thin avoid wide collars as they make your shoulders look too narrow.
Once you have a brand and size that sits, memorise it: if a salesperson knows what they are doing they should be able to offer something similar if your favourite brand is out of stock. Invest in good quality shirts for work/ dress - there is nothing worse than a shirt that is badly made from a semi-transparent material with pulled seams and threads hanging off. Business shirts are always in stock, change very little and are often on sale so take advantage by buying when they are cheaper.
Plain short sleeve shirts (available from Just Jeans, Jeans West, Hallensteins and trendier clothing shops etc) are an easy option to dress up or down with dress trousers, casual khakis, jeans or 'long shorts', depending on the occasion.
One last tip - don't tuck you shirt tight down into your pants - unless of course you want to look like a 1950's schoolboy who was dressed by his mother. Tuck your shirt in loosely but flat, do up your fly and waistband then raise your hands above your head - that is how loose your shirt should be all round.
Jackets and Suits: A suit is probably the most expensive investment you will make in your wardrobe. Wait for a sale if possible or at the very least find a good shop that offers a second pair of trousers free as these will wear out first. Sales can be a bit of a nightmare so it is best to be prepared ahead of time. Do your homework first: visit a couple of good quality suit shops and get measured and fitted by someone who knows what they are doing. Then wait for the sale and grab something the same or similar for half price.
Suit styles do date and if you don't wear a suit to work you will probably never need one. Besides if you need one to go to a wedding once a year, a rental suit is not a bad option - particularly if you accidentally spill a few beers on the night.
Suits are expensive and you want to get something that will last. A good salesperson will be able to tell you the best style for your build. Choose a suit from the conservative but fashionable end of the spectrum, as you don't want to be spending another couple of thousand dollars again next year. Generally a two-button jacket will work if you have wider hips and want to appear taller while taller guys will suit a three-button style. Choose a classic style or a style that will be staying in for another couple of years in a standard colour. Beige safari suits should be avoided unless you are a standing for president of the local bowling club or an endocrinologist. And never buy a white suit or jacket unless you want a part on Fantasy Island.
Jackets are a great investment as they hide binding, square off shoulders and can be used to dress up a casual outfit quickly without getting out of your favourite shirt and jeans. Choose a length to suit your height and build and if necessary get a tailor to adjust the sleeves - never roll them up.
Ties: Ties can be expensive but are often on sale so look around and increase your selection gradually. If you need to wear one for work, check out what is the office standard for your area and buy accordingly. Once you have the basics covered then you can experiment with your own style and taste. If you haven't worn a tie before it can take a bit of getting used to so do some trial runs at home over a weekend or in the evening. That way you can avoid looking uncomfortable in the office or at dinner.
One last comment: if you wear a bowtie, buy a proper one and learn how to tie it - it isn't hard and it has a lot more panache than the ready-made variety.